We are happy to advise you that the board of directors of AIM Bancshares, Inc. (“AIM”) has unanimously approved the merger (the “merger”) of AIM into Heartland Financial USA, Inc. (“Heartland”) in accordance with an Agreement and Plan of Merger dated as of February 11, 2020 (the “merger agreement”). Before we can complete the merger, we must obtain the approval of the AIM shareholders. We are sending you this proxy statement/prospectus to ask you to vote in favor of approval of the merger agreement. The AIM board of directors unanimously recommends that you vote “FOR” approval of the merger agreement.

In the merger, AIM will merge with and into Heartland, and holders of shares of AIM common stock will receive 207.0 shares of Heartland common stock (the “stock exchange ratio”) and $685.00 of cash (the “cash exchange ratio”) for each share of AIM common stock owned by such holders immediately prior to the effective time of the merger, subject to adjustment as described below, plus cash in lieu of any fractional shares. As of the date of this proxy statement/prospectus, AIM shareholders owned 24,553.98 shares of AIM common stock.

Holders of options to acquire shares of AIM common stock outstanding and unexercised on the closing date of the merger will receive a cash payment equal to the product of (a) the number of shares of AIM common stock subject to such AIM stock option, and (b) the excess of (i) an amount determined by (A) multiplying 207.0 by the volume-weighted average trading prices for shares of Heartland common stock for each of the fifteen (15) consecutive trading days ending on and including the trading day immediately preceding the fifth business day preceding the closing date, rounded to three decimal places, as quoted on the NASDAQ Global Select Market on such trading day plus (B) $685.00 (subject to adjustment as described below), less (ii) the exercise price per share of such AIM stock option (the amount determined by the foregoing formula, the “option consideration”), less any applicable taxes required to be withheld. If the option consideration for an AIM stock option is a negative number, the holder of the stock option will not be entitled to any such cash payment. As of the date of this proxy statement/prospectus, 1,735 shares of AIM common stock are reserved for issuance to holders of AIM stock options.

The stock exchange ratio is fixed and, except as described below, will not be adjusted to reflect changes in the price of Heartland common stock occurring prior to the completion of the merger. If the price of Heartland common stock drops below a certain level and the performance of Heartland common stock is also below a certain level of performance of the KBW NASDAQ Regional Banking Index, as described under the section titled “The Merger Agreement—Termination” in this proxy statement/prospectus, AIM may exercise a “walk-away” right to terminate the merger agreement unless Heartland increases, at its option, either the stock exchange ratio or the cash exchange ratio by exercising a “top-up” option.

Alternatively, if the price of Heartland common stock increases above a certain level and the performance of Heartland common stock is also above a certain level of performance of the KBW NASDAQ Regional Banking Index, as described under the section titled “The Merger Agreement—Termination” in this proxy statement/prospectus, Heartland may exercise a “walk-away” right to terminate the merger agreement unless AIM accepts, at its option, either a decrease in either the stock exchange ratio or cash exchange ratio to avoid Heartland's termination of the merger agreement.

The cash exchange ratio is fixed, but may be adjusted in two instances. First, in the event the closing date of the merger occurs on or after June 30, 2020 and AIM's Adjusted Tangible Common Equity (as defined in this proxy statement/prospectus in the section titled “The Merger Agreement—The Merger—Determination of Merger Consideration”) as of the last business day of the month immediately preceding the month in which the closing date of the merger occurs (the “determination date”) is less than $145,000,000 (the “minimum equity”), then the cash component of the merger consideration will be reduced by an amount equal to the amount by which the Adjusted Tangible Common Equity is below the minimum equity. If the closing date of the merger occurs before June 30, 2020, the minimum equity will be reduced by an amount equal to the product of $70,000 multiplied by the number of calendar days from the effective time through June 30, 2020 for purposes of determining whether a downward adjustment of the cash exchange ratio will be made.

Second, if AIM's Adjusted Tangible Common Equity as of the determination date is greater than $148,000,000, the cash component of the merger consideration will be increased by an amount equal to the lesser of (a) $5,000,000 and (b) the amount by which the Adjusted Tangible Common Equity is above $148,000,000.

Based on the closing price of a share of Heartland common stock as of February 10, 2020 (the last trading day before the merger agreement was executed) of $49.88, the aggregate merger consideration was valued at $280.4 million with (a) AIM shareholders receiving aggregate consideration of approximately $270.3 million, or $11,010.16 for each share of AIM common stock and (b) holders of AIM stock options receiving aggregate option consideration of approximately $10.0 million. Based on the price of a share of Heartland common stock as of May 15, 2020 (the last trading date before the date of this proxy statement/prospectus) of $26.76, the aggregate merger consideration was valued at $155.4 million with (i) AIM shareholders receiving aggregate consideration of approximately $152.8 million, or $6,224.32 for each share of AIM common stock and (ii) holders of AIM stock options receiving aggregate option consideration of approximately $2.6 million. These valuations are based on the assumption that no adjustments will be made to the cash exchange ratio based on AIM's Adjusted Tangible Common Equity. As of March 31, 2020, the book value per share of AIM common stock was $6,779.50 and the tangible book value per share of AIM common stock was $5,768.47. Heartland common stock is listed on the NASDAQ Global Select Market under the symbol “HTLF.” Because the market price for Heartland common stock will fluctuate prior to the effective date of the merger and the Adjusted Tangible Common Equity of AIM may increase or decrease, the value and amount, respectively, of the actual consideration you will receive may be different from the amounts described above.

At the closing of the merger, Heartland will assume all obligations of AIM with respect to certain subordinated debentures (which have a par value of approximately $3,100,000) issued in connection with a trust preferred securities financing by AIM.

To complete the merger, we must receive certain regulatory approvals and the holders of at least two-thirds of the issued and outstanding shares of AIM common stock entitled to vote must approve the merger agreement.

At its 2020 annual meeting of shareholders (the “annual meeting”), AIM will be seeking the shareholder approval necessary to complete the merger. The annual meeting will be held at              , at         local time on       , 2020, unless adjourned to a later date. At the annual meeting, AIM will ask its shareholders to consider and vote upon the following matters:

Your vote is important. Whether or not you plan to attend the annual meeting, please submit voting instructions for your shares of AIM common stock in accordance with the instructions contained in this proxy statement/prospectus. If you mark “ABSTAIN” on your proxy card or do not vote your shares of AIM common stock at the annual meeting, it will have the same effect as voting against the merger.

We urge you to read this proxy statement/prospectus carefully before voting, including the section titled “Risk Factors.” This proxy statement/prospectus gives you detailed information about the merger and includes a copy of the merger agreement as Appendix A.

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved the securities to be issued in connection with the merger or determined if this proxy statement/prospectus is truthful or complete. Any representation to the contrary is a criminal offense.

The securities that Heartland is offering pursuant to this document are not savings accounts, deposits or other obligations of any bank and are not insured or guaranteed by the Federal Deposit Insurance Corporation or any other governmental agency.

The date of this proxy statement/prospectus is    , 2020, and it is first being mailed to AIM shareholders on or about   , 2020.

AIM Bancshares, Inc. (“AIM”) will hold an annual meeting of its shareholders (the “annual meeting”) at              , at      local time on     , 2020, to consider and vote upon the following matters:

Upon completion of the merger, each share of AIM common stock will be converted into the right to receive shares of Heartland common stock and cash, and each AIM stock option will be converted into the right to receive a cash payment equal to the amount of merger consideration per share received by holders of AIM common stock less the exercise price of the option to acquire such share of AIM common stock. If the exercise price per share of an AIM stock option exceeds the merger consideration per share, the holder of the stock option will not be entitled to receive any such cash payment. The accompanying proxy statement/prospectus contains a detailed discussion of the merger and certain related transactions, and includes a copy of the merger agreement as Appendix A.

The board of directors has fixed    , 2020 as the record date for the annual meeting. Holders of record of AIM common stock at the close of business on such date are entitled to notice of, and to vote on the above proposals.

The AIM board of directors has unanimously approved the merger agreement and unanimously recommends that holders of AIM common stock vote “FOR” approval of the merger proposal. In addition, the AIM board of directors unanimously recommends that you vote for “FOR” the election of the AIM director nominees and “FOR” the adjournment of the annual meeting for the purpose described above.

AIM shareholders who do not vote in favor of the merger agreement and who strictly comply with Chapter 10, Subchapter H of the Texas Business Organizations Code have the right to assert dissenters' rights under that statute. For a description of the procedures that must be followed to make written demand for dissenters' rights, see the copy of the statute which is attached as Appendix B to this proxy statement/prospectus. In addition, a summary of the procedures to be followed in order to obtain payment for dissenting shares is set forth under the section titled “Dissenters' Rights of AIM Shareholders” in the proxy statement/prospectus.

Whether or not you plan to attend the annual meeting, please vote your shares of AIM common stock using one of the methods described on the enclosed proxy card. Any holder of AIM common stock present at the annual meeting may vote in person instead of voting prior to the annual meeting, and a vote by any such holder prior to the annual meeting may be revoked in writing at any time before or at the annual meeting. The presence of an AIM shareholder at the annual meeting will not automatically revoke that shareholder's previous vote. An AIM shareholder may revoke such shareholder's vote by (a) filing with the Secretary of AIM a written notice of revocation, (b) delivering to AIM a duly executed proxy bearing a later date, or (c) attending the meeting and voting in person.

COVID-19. In March 2020, the outbreak of COVID-19 was recognized as a pandemic by the World Health Organization. The spread of COVID-19 has created a global public health crisis that has resulted in unprecedented uncertainty, volatility and disruption in financial markets and in governmental, commercial and consumer activity in the United States, as well as globally. Governmental responses to the COVID-19 pandemic have included orders closing businesses not deemed essential and directing individuals to restrict their movements, observe social distancing and shelter in place. These actions, together with responses to the COVID-19 pandemic by businesses and individuals, have resulted in rapid decreases in commercial and consumer activity, temporary closures of many businesses, which have led to a loss of revenues and a rapid increase in unemployment, material decreases in commodity prices and business valuations, disruptions in global supply chains, market downturns and volatility, changes in consumer behavior related to fears from the COVID-19 pandemic, emergency response legislation and an expectation that the Federal Reserve will maintain a low interest rate environment for the foreseeable future.

Heartland's business is dependent upon the willingness and ability of its employees and customers to conduct banking and other financial transactions. If the global response to contain COVID-19 escalates further or is unsuccessful, Heartland could experience a material adverse effect on its business, financial condition, results of operations, liquidity and prospects. The full extent of the impact of the COVID-19 pandemic, and resulting measures to curtail its spread, will depend on future developments that are highly uncertain, including the scope,

severity and duration of the pandemic, the actions taken to contain COVID-19 or mitigate its impact, and the direct and indirect economic effects of the COVID-19 pandemic and containment measures.

Adoption of ASU 2016-13, “Financial Instruments – Credit Losses (Topic 326).” On January 1, 2020, Heartland adopted ASU 2016-13, “Financial Instruments - Credit Losses (Topic 326),” commonly referred to as “CECL.” The impact of Heartland's adoption of CECL on January 1, 2020 resulted in the following:

The allowance calculation under CECL is an expected loss model, which encompasses expected losses over the life of loan and held to maturity securities portfolios, including expected losses due to changes in economic conditions and forecasts, such as those caused by the COVID-19 pandemic. Heartland recorded $21.5 million of provision for credit losses in the first quarter of 2020, primarily due to a deteriorating economic outlook resulting in an increase in expected credit losses.

Governmental authorities worldwide have taken unprecedented measures to stabilize economic markets and support economic growth. The success of these measures is unknown, and they may not be sufficient to address the negative economic effects of COVID-19 or avert severe and prolonged reductions in economic activity.

Heartland's subsidiary banks and AimBank are participating lenders in the PPP, a loan program administered through the SBA, that was created to help eligible businesses, organizations and self-employed persons fund their operational costs during the COVID-19 pandemic. Under this program, the SBA guarantees 100% of the amounts loaned under the PPP. The PPP opened on April 3, 2020; however, because of the short window between the passing of the CARES Act and the opening of the PPP, there is some ambiguity in the laws, rules and guidance regarding the operation of the PPP, which has exposed Heartland and AIM to risks relating to noncompliance with the PPP. For instance, other financial institutions have experienced litigation related to their procedures used in processing applications for the PPP. Under the PPP, lending banks are generally entitled to rely on borrower representations and certifications of eligibility to participate in the PPP, and lending banks may also be held harmless by the SBA in certain circumstances for actions taken in reliance on borrower representations and certifications. Notwithstanding the foregoing, Heartland's subsidiary banks and AimBank have been, and may continue to be, exposed to credit risk on PPP loans if a determination is made by the SBA that there is a deficiency in the manner in which the loan was originated, funded or serviced. If a deficiency is identified, the SBA may deny its liability under its guaranty, reduce the amount of the guaranty, or, if it has already paid under the guaranty, seek recovery of any loss related to the deficiency from Heartland's subsidiary banks and AimBank.

Heartland's subsidiary banks and AimBank's participation in and execution of these and other measures taken by governments and regulatory authorities in response to the COVID-19 pandemic could result in reputational harm and may also lead to litigation, including class actions, or regulatory and government actions and proceedings. Such actions and proceedings may result in judgments, settlements, penalties and fines levied against Heartland's subsidiary banks and AimBank.

Heartland's and AimBank's current period results of operations are not necessarily indicative of results that may be expected for any other interim period or for 2020 as a whole. During the quarter ended March 31, 2020, the COVID-19 outbreak had a material impact on the provision for credit losses of Heartland and AIM, but they are unable to fully predict the impact that COVID-19 will have on its business financial position, results of operations, liquidity and prospects due to numerous uncertainties. Heartland and AIM will continue to assess the potential impacts on their financial positions and results of operations.

The extent to which the COVID-19 pandemic impacts Heartland's and AIM's businesses, results of operations and financial conditions will depend on future developments, which are highly uncertain and are difficult to predict, including, but not limited to, the duration and spread of COVID-19, its severity, the actions to contain the virus or treat its impact, and how quickly and to what extent normal economic and operating conditions can resume. Even after the COVID-19 pandemic has subsided, Heartland and AIM may continue to experience materially adverse impacts to their businesses as a result of the COVID-19’s global economic impact, including the availability of credit, adverse impacts on liquidity and any recession or depression that has occurred or may occur in the future.

There are no comparable recent events that provide guidance as to the effect the spread of COVID-19 as a global pandemic may have, and, as a result, the ultimate impact of COVID-19 is highly uncertain and subject to change. Neither Heartland nor AIM knows the full extent of the impacts of COVID-19 on its business, operations or the economy as a whole. However, the effects could have a material impact on Heartland's and AIM's results of operations, and, in the case of Heartland, heighten many of the known risks described in the “Risk Factors” sections of its Annual Report on Form 10-K for the year ended December 31, 2019 and its Quarterly Report on Form 10-Q for the quarter ended March 31, 2020.

At the effective time of the merger, each share of AIM common stock will be converted into the right to receive 207.0 shares of Heartland common stock (the “stock exchange ratio”) and $685.00 of cash (the “cash exchange ratio”), subject to adjustment as described herein. The stock exchange ratio will not increase based on

fluctuations in the market price of Heartland common stock. However, if (a) the price of Heartland common stock decreases below certain levels and (b) the performance of the Heartland common stock is also below a certain level of performance of the KBW NASDAQ Regional Banking Index, then AIM may invoke its “walk-away” right to terminate the merger agreement. Heartland may subsequently exercise its right to make a “top-up” election and increase, at its option, either the stock exchange ratio or cash exchange ratio to void the “walk-away” right as described in the section of this proxy statement/prospectus titled “The Merger Agreement—Termination.” Alternatively, if (a) the price of Heartland common stock increases above a certain level and (b) the performance of Heartland common stock is also above a certain level of performance of the KBW NASDAQ Regional Banking Index, as described under the section titled “The Merger Agreement—Termination” in this proxy statement/prospectus, Heartland may exercise a “walk-away” right to terminate the merger agreement unless AIM agrees to a decrease, at its option, in either the stock exchange ratio or cash exchange ratio used to calculate the merger consideration to avoid the termination of the merger agreement by Heartland. The market value of Heartland common stock has declined significantly since Heartland and AIM entered into the merger agreement and will continue to vary in the future due to changes in the business, operations or prospects of Heartland, developments related to the coronavirus pandemic, market and economic conditions, market assessments of the merger, regulatory considerations, and other factors both within and beyond the control of Heartland. Therefore, prior to and at the time of the annual meeting, AIM's shareholders will not know or be able to calculate the market value of the Heartland common stock they will receive upon completion of the merger.

The cash exchange ratio will determine the amount of cash that AIM shareholders will receive in the merger, which is dependent upon the Adjusted Tangible Common Equity of AIM as of the determination date and will be reduced to the extent that Adjusted Tangible Common Equity is less than $145 million. Reductions in Adjusted Tangible Common Equity may result from higher loan loss provisions, ordinary business conditions that impact the net interest and noninterest income of AIM, the financial effects of the coronavirus pandemic or more general market and economic conditions that impact AIM operations.

The spread of the coronavirus throughout the United States, and the measures taken by national, regional and local governmental authorities attempting to contain the spread and impact of the coronavirus, such as travel bans and restrictions, quarantines, shelter in place orders, and limitations on business activity, including closures, are, among other things, severely restricting economic activity in the United States and the Texas and New Mexico banking markets of FB&T and AIM in particular, which is disrupting national and regional supply chains, lowering asset valuations, significantly increasing unemployment and underemployment levels, decreasing liquidity in markets for certain securities and causing significant volatility and disruptions in the financial markets, Given the ongoing and dynamic nature of the circumstances, it is difficult to predict the impact of the coronavirus outbreak on businesses of Heartland and AIM, and there is no guarantee that efforts by Heartland and AIM to address the adverse impacts of the coronavirus will be effective. The extent of such impact will depend on future developments, which are highly uncertain and cannot be predicted, including new information which may emerge concerning the continued severity of COVID-19 and actions taken to contain COVID-19 or its impact, among others. The merger may also be delayed and adversely affected by the COVID-19 outbreak, and become more costly. Each of Heartland and AIM may also incur additional costs to remedy economic disruptions caused by the effect of the COVID-19 crisis, which are expected to adversely affect its financial condition and results of operations.

AIM common stock is not traded on any public markets. Any market for AIM common stock has been illiquid and irregular. This lack of liquidity makes it difficult to determine the fair value of AIM common stock.

Before the merger may be completed, approvals must be obtained from federal and state bank regulators, including the FRB, the FDIC and the TDB. The New Mexico Branch Transfers are also subject to receipt of

approvals from the FDIC, the TDB and the NMFID. The bank regulators will consider, among other factors, the competitive impact of the merger and the New Mexico Branch Transfers, the financial and managerial resources of Heartland and AIM, the convenience and needs of the communities to be served, the capital position of the combined company, safety and soundness, legal and regulatory compliance matters, and Community Reinvestment Act matters, and may impose conditions, limitations, obligations or restrictions on the completion of the merger or require changes to or waivers of certain terms of the merger agreement. There can be no assurance as to whether regulatory approvals will be received, the timing of those approvals, or whether any conditions, limitations, obligations or restrictions will be imposed and, if imposed, whether such conditions, limitations, obligations or restrictions will have the effect of preventing or materially delaying the completion of the merger, imposing additional material costs on or materially limiting the revenues of Heartland following the merger, or otherwise materially reducing the anticipated benefits of the merger. Further, the effects of the coronavirus may delay the regulatory approvals necessary to complete the merger.

AIM shareholders should bear in mind that regulatory approval reflects only the view that the merger does not contravene applicable competitive standards imposed by law, and that the merger is consistent with regulatory policies relating to safety and soundness. Further, regulatory approval is not an opinion that the proposed merger is favorable to the shareholders of either party to the merger from a financial point of view or that the regulatory authority has considered the adequacy of the terms of the merger. Regulatory approval is not an endorsement or recommendation of the merger.

Certain executive officers and directors of AIM have interests in the merger that are different from, or in addition to, the interests of AIM's shareholders generally. For a description of these interests, see the sections titled “Background and Reasons for the Merger—Certain Interests of AIM Directors and Executive Officers in the Merger.” These interests and arrangements may cause the directors and executive officers to view the merger proposal differently than you may view it. AIM's board of directors was aware of these interests and considered them, among other matters, when making a decision to approve the merger agreement and recommend that AIM shareholders approve the merger agreement.

Consummation of the merger is subject to customary conditions to closing in addition to the receipt of required bank regulatory approvals and approval of the merger agreement by the requisite vote of the AIM shareholders. If any condition to the merger is not satisfied or waived, the merger will not be completed. In addition, Heartland and AIM may terminate the merger agreement under certain circumstances even if the merger agreement is approved by the AIM shareholders, including the circumstance that the merger has not been completed on or before September 30, 2020. If the merger is not completed, the trading prices of Heartland common stock may decline to the extent that the current price reflects a market assumption that the merger will be completed. Also, the continued operations of AIM may be impaired because of costs, the departure of employees and customers, or other dislocation caused by the terminated merger. In addition, neither Heartland nor AIM would realize any of the expected benefits of having completed the merger. In addition, if the merger is not completed, Heartland and AIM may experience negative reactions from their respective shareholders, customers and employees. Heartland and AIM also could be subject to litigation related to any failure to complete the merger or to proceedings commenced by Heartland or AIM against the other party seeking damages or to compel the other to perform its obligations under the merger agreement. These factors and similar risks could have an adverse effect on the results of operations and business of Heartland and AIM and the price of Heartland common stock. For more information on the closing conditions to the merger, see the section titled “The Merger Agreement—Conditions to Completion of the Merger.”

Upon completion of the merger, AIM shareholders will become Heartland stockholders, and their rights as shareholders will be governed by the Delaware General Corporation Law and the Heartland certificate of

incorporation and bylaws, as they may be amended from time to time. The rights associated with AIM common stock are different from the rights associated with Heartland common stock. See the section titled “Comparison of Rights of Holders of Heartland Common Stock and AIM Common Stock.”

Until the completion of the merger, with certain exceptions, AIM is prohibited from initiating, soliciting, knowingly encouraging or taking other actions to facilitate any inquiries, discussions or the making of any proposals that may lead to an acquisition proposal, such as a merger or other business combination transaction, with any entity other than Heartland. In addition, AIM has agreed to pay a termination fee to Heartland if the merger agreement is terminated in specified circumstances, including the circumstance in which AIM terminates the merger agreement to enter into a superior proposal with another entity. These provisions could discourage other companies from trying to acquire AIM even though those other companies might be willing to offer greater value to AIM's shareholders than Heartland has offered in the merger proposal. See the sections titled “The Merger Agreement—Termination” and “The Merger Agreement—Termination Fee and Payment of Expenses” for more information about the termination fee and AIM's restrictions on solicitation.

Magstar, AIM's financial advisor in connection with the merger, has delivered to the board of directors of AIM its opinion dated as of February 10, 2020. The Magstar opinion states that as of such date, and based upon and subject to the factors and assumptions set forth therein, the consideration to be paid to the holders of the outstanding shares of AIM common stock pursuant to the merger agreement was fair from a financial point of view to AIM shareholders. The opinion does not reflect changes that may occur or may have occurred after the date of such opinion, including, increases in the severity of the coronavirus, the decrease in the trading price of Heartland common stock, changes to the operations and prospects of AIM, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which such opinion is based, may materially alter or affect the estimated valuation conclusions reached in such opinion. The opinion does not speak as of any date other than its date.

As noted above, COVID-19 has significantly disrupted economic markets and its prolonged economic impact is uncertain. Some economists and major investment banks have expressed concern that the continued spread of the virus in the United States and globally could lead to a world-wide recession or depression. If Heartland is unable to recover from any business disruption resulting from the COVID-19 pandemic on a timely basis following the closing of the merger, Heartland's business, results of operations, financial condition, liquidity and prospects would be adversely affected and the market price of shares of Heartland common stock could decline. The efforts to integrate the businesses of FB&T and AimBank may also be adversely affected by the COVID-19 outbreak.

The combination of AIM with Heartland may cause Heartland to have difficulty in achieving the full strategic objectives and operating efficiencies it hopes to achieve from the merger. The success of the merger will depend on a number of factors, including Heartland's ability to:

These factors could contribute to the combined company consisting of Heartland and AIM not achieving the expected benefits from the merger within the desired time frames, if at all.

Risks that may impact Heartland's net income and the strength of its balance sheet depend on a number of factors, including the following: (i) the strength of the national economy and the economies of local communities in which Heartland conducts business; (ii) the economic and other effects of the coronavirus; (iii) the economic impact of past and any future terrorist threats and attacks and any acts of war; (iv) changes in state and federal banking laws and regulations and governmental policies affecting financial institutions; (v) changes in interest rates and prepayment rates of Heartland's loans; (vi) increased competition in the financial services sector and the inability of Heartland to attract new customers; (vii) changes in technology and Heartland's ability to develop and maintain secure and reliable electronic systems; (viii) the potential impact of future acquisitions and Heartland's ability to successfully integrate acquired banks (which are discussed in the risk factor below relating to acquisitions by Heartland); (ix) the loss of key executives or employees; (x) changes in consumer spending; (xi) unexpected outcomes of existing or new litigation involving Heartland; and (xii) changes in accounting policies and practices. These factors are described in the section of this proxy statement/prospectus titled “Forward-Looking Statements” and are discussed in detail in Heartland's Annual Report on Form 10-K incorporated by reference into this proxy statement/prospectus.

The coronavirus, the general stock market downturn, industry factors and general economic and political conditions and events recently have caused a decline in Heartland's stock price, and these factors, as well as interest rate changes, unfavorable credit loss trends, or unforeseen events such as terrorist attacks could cause Heartland's stock price to be volatile regardless of its operating results. If a recession or depression results from the continued spread of the coronavirus, the price of Heartland's common stock could continue to decline.

Heartland intends to continue to investigate strategic acquisitions of other bank holding companies, banks and other businesses after the merger. Acquiring other banks and businesses will involve risks commonly associated with acquisitions, including:

These risks and uncertainties should be considered in evaluating forward-looking statements, and undue reliance should not be placed on these statements.

The forward-looking statements included in this proxy statement/prospectus are made only as of the date of this proxy statement/prospectus, and Heartland and AIM undertake no obligation to update any statement in light of new information or future events. Further information concerning Heartland and its business, including additional factors that could materially affect Heartland's financial results, is included in Heartland's filings with the Securities and Exchange Commission (the “SEC”). See the section titled “Where You Can Find More Information.”

The annual meeting will be held at             , at      local time on     , 2020.

At the annual meeting, holders of shares of AIM common stock will be asked to consider:

The AIM board of directors unanimously recommends that you vote “FOR” the approval of the merger proposal and “FOR” the election of the AIM director nominees set forth and described below under the section titled “The AIM Annual Meeting—Election of AIM Directors.” In addition, the AIM board of directors unanimously recommends that you vote “FOR” the adjournment of the annual meeting, if necessary or appropriate, to permit further solicitation of proxies if there are not sufficient votes at the time of the annual meeting to approve the merger proposal.

After you have carefully read this proxy statement/prospectus and have decided how you wish to vote your shares of AIM common stock, please indicate on the enclosed proxy card your vote and sign, date and mail your proxy card in the enclosed postage paid return envelope as soon as possible so that your shares of AIM common stock may be represented at the annual meeting.

If your shares of AIM common stock are indirectly owned by you through the KSOP, you will receive separate voting instructions from the KSOP trustees with your proxy materials. In order to have your shares voted at the annual meeting by the KSOP trustees, you must follow such voting instructions.

You may change your vote at any time by (i) filing with the Secretary of AIM a written notice of revocation, (ii) delivering to AIM a duly executed proxy card bearing a date later than the date of your previous proxy card, or (iii) attending the annual meeting and voting in person. Your presence at the annual meeting will not automatically revoke your proxy. All written notices of revocation and other communications with respect to revocation of proxies in connection with the annual meeting should be addressed as follows:

All shares of AIM common stock, unless the vote is revoked, will be voted in accordance with the instructions received from each AIM shareholder. If you submit a proxy card and make no specification on your proxy card as to how you want your shares of AIM common stock voted before signing and returning it, your proxy will be voted “FOR” the merger proposal, “FOR” the election of the AIM director nominees, and “FOR” the adjournment proposal, if necessary or appropriate.

AIM will bear the entire cost of soliciting votes from you. If necessary, AIM may also use several of its regular employees, who will not be specially compensated, to solicit the vote from holders of AIM common stock, either personally or by telephone, facsimile, email or letter.

The AIM board of directors has fixed the close of business on      , 2020 as the record date for determining the holders of AIM common stock entitled to receive notice of and to vote at the annual meeting. At that time,      shares of AIM common stock were outstanding. As of the record date, there were approximately      holders of record of AIM common stock.

General. The presence, in person or by proxy, of the holders of a majority of the issued and outstanding shares of AIM common stock entitled to vote at the meeting is necessary to constitute a quorum at the annual meeting. Abstentions, if any, will be counted solely for the purpose of determining whether a quorum is present.

Approval of the merger proposal requires the affirmative vote of the holders of at least two-thirds of the issued and outstanding shares of AIM common stock. If you mark “ABSTAIN” on your proxy card, fail to vote by proxy or in person at the annual meeting or fail to submit valid proxy instructions to your broker, bank or other nominee with respect to the merger proposal, it will have the effect of a vote “AGAINST” the merger proposal.

Directors will be elected by the affirmative vote of the holders of a majority of the shares of AIM common stock entitled to vote in the election of directors and represented in person or by proxy at the annual meeting. If you are represented in person or by proxy at the annual meeting but abstain or fail to vote on the proposal to elect the AIM director nominees, it will have the effect of a vote “AGAINST” such proposal. If you are not represented in person or by proxy at the annual meeting, and therefore, fail to vote prior to or at the annual meeting, it will have no effect on the proposal to elect the AIM director nominees.

Approval of the adjournment proposal, if necessary or appropriate, requires a majority of the votes cast with respect to the proposal. With respect to the adjournment proposal, if you mark “ABSTAIN” on your proxy card or fail to vote prior to or at the annual meeting, it will have no effect on the adjournment proposal.

You are entitled to one vote for each share of AIM common stock you held as of the record date. As of the record date of the annual meeting, directors and executive officers of AIM and their respective affiliates held      % of the outstanding shares of AIM common stock.

The failure to vote prior to the annual meeting or in person at the annual meeting will have the same effect as a vote against the merger agreement, which is required to be approved by two-thirds of the issued and outstanding shares of AIM common stock. Abstentions also will have the same effect as a vote against the merger proposal. Accordingly, the AIM board of directors urges holders of AIM common stock to vote on the merger proposal prior to or at the annual meeting.

Voting Agreement. Pursuant to a shareholder voting agreement, certain holders of AIM common stock have agreed to vote their shares in favor of the merger proposal. Under the terms of the shareholder voting agreement, such shareholders have also appointed Heartland as their proxy for voting their shares of AIM common stock at the annual meeting with respect to the merger proposal. The holders of AIM common stock that have signed the shareholder voting agreement have the right to vote, or direct the voting of,  % of the outstanding shares of AIM common stock as of the record date. In the event the merger agreement is terminated, the shareholder voting agreement will terminate, and none of the AIM shareholders who have signed such agreement will be required to vote in favor of the merger proposal.

Brokers, banks and other nominees who hold shares of AIM common stock in “street name” for a beneficial owner of those shares typically have the authority to vote in their discretion on “routine” proposals when they have not received instructions from beneficial owners. However, brokers, banks and other nominees are not allowed to exercise their voting discretion with respect to the approval of matters determined to be

“non-routine,” without specific instructions from the beneficial owner. Broker non-votes are shares held by a broker, bank or other nominee that are represented at the AIM annual meeting, but with respect to which the broker, bank or other nominee is not instructed by the beneficial owner of such shares to vote on the particular proposal and the broker, bank or other nominee does not have discretionary voting power on such proposal. The merger proposal is a non-routine matter. Accordingly, if your broker, bank or other nominee holds your shares of AIM common stock in “street name,” your broker, bank or other nominee will vote your shares of AIM common stock with respect to the merger proposal only if you provide instructions on how to vote by filling out the voter instruction form sent to you by your broker, bank or other nominee with this proxy statement/prospectus. If you do not instruct your broker, bank or other nominee on how to vote your shares of AIM common stock on the merger proposal, your broker, bank or other nominee may not vote your AIM common stock, which will have the same effect as a vote against the merger proposal for purposes of the required vote. You should therefore provide your broker, bank or other nominee with instructions as to how to vote your shares of AIM common stock. Please note that you may not vote your shares of AIM common stock held in “street name” on the merger proposal by returning a proxy card directly to AIM or by voting in person at the annual meeting unless you provide a “legal proxy,” which you must obtain from your broker, bank or other nominee.

The bylaws of AIM require that AIM hold an annual meeting of shareholders each year and that AIM directors be elected at the annual shareholder meeting. The annual meeting will constitute AIM's 2020 annual meeting of shareholders, and, therefore, AIM directors must be elected. In the event the holders of AIM common stock do not approve the merger proposal at the annual meeting, AIM will not be required to hold an additional meeting of shareholders to elect directors because directors will have been elected at the annual meeting.

The board of directors of AIM has nominated the following four persons to stand for election at the annual meeting: Buford Duff; Jeremy Ferrell; Scott L. Wade; and Kenneth D. Willmon. Each nominee is currently a director of AIM, and has served as a director for the periods indicated below. The following information is furnished with respect to each AIM director nominee:

Holders of AIM common stock are also being asked to vote at the annual meeting on a proposal to adjourn the meeting. However, the annual meeting will only be adjourned if there are not sufficient votes at the time of the annual meeting to approve the merger proposal. The annual meeting will be adjourned if it is necessary and appropriate to permit further solicitation of proxies in order to obtain AIM shareholder approval of the merger proposal.

AIM is not currently aware of any business to be acted upon at the annual meeting other than the matters discussed in this proxy statement/prospectus.

The merger agreement provides that AIM will be merged with and into Heartland. Each share of AIM common stock outstanding immediately prior to the effective time of the merger will be converted, upon completion of the merger, into the right to receive 207.0 shares of Heartland common stock and $685.00 in cash, subject to adjustment as further described in this proxy statement/prospectus. Cash will be paid in lieu of any fractional shares. At or immediately after the effective time of the merger, AimBank will be merged with and into FB&T.

The board of directors and management of AIM regularly review AIM's future prospects for earnings and asset growth as well as the implementation and viability of AIM's strategic initiatives. From time to time, the board of directors and management of AIM will review and discuss AIM's long-term objectives and consider ways to enhance shareholder value and performance of the consolidated organization. This strategic planning exercise generally included an evaluation of the merits and drawbacks of (a) continuing to operate as an independent institution, (b) continued expansion through the strategic acquisition of other institutions and branch offices, and (c) entering into a strategic merger with another financial institution. These reviews and strategic discussions have focused on, among other things, prospects and developments in the financial services industry, in the regulatory environment, in the economy and financial markets, and the implications of such developments for financial institutions in general and AIM and the West Texas market in particular. Management of AIM has also engaged in, from time to time and as part of its stated mergers and acquisitions strategy, discussions with executives of other institutions in the financial services industry, including with respect to potential strategic transactions to enhance shareholder value, liquidity and return on investment. AIM has periodically received inquiries from potential acquirors and other merger partners in the industry.

Heartland's board of directors and management regularly reviews Heartland's business strategies, opportunities and challenges, with the goal of enhancing stockholder value. These strategic reviews have focused on, among other things, the business and regulatory environment facing Heartland and financial institutions generally, as well as ongoing consolidation in the financial services industry. The reviews conducted by Heartland's board of directors and management have included discussions regarding potential transactions that would further Heartland's strategic objectives, and the potential benefits and risks of these transactions. Through acquisition and organic growth, Heartland's goal is to reach at least $1.0 billion in assets in each state where Heartland operates.

In December 2018, Scott L. Wade, Chairman of the Board and Chief Executive Officer of AIM, and Jeremy Ferrell, Secretary, Treasurer and a Director of AIM, contacted representatives of Hillworth LLC (“Hillworth”), to discuss potential business combination opportunities, including the prospect of merging AIM into a larger institution, and to identify potential strategic merger partners. As part of these preliminary discussions with Hillworth, Messrs. Wade and Ferrell expressed the AIM board's desire to continue executing AIM's growth strategy both organically and through acquisitions, but that AIM would also be interested in establishing relationships with potential strategic merger partners. Messrs. Wade and Ferrell also indicated to Hillworth the AIM board's expectations regarding the economic terms of a proposed transaction.

During December 2018 and January 2019, AIM management met several times with representatives of Hillworth to discuss market conditions and to identify potential strategic merger partners. At the request of AIM management, Hillworth performed additional research and analysis during this time period to identify potential merger partners. As a result of these discussions and analyses, AIM management and Hillworth identified four institutions with which to initiate discussions regarding a potential business combination, as well as planned a course of action for determining the interest of each institution in such a transaction. The four institutions identified were Heartland, a second institution, referred to as Bank A, a third institution, referred to as Bank B, and a fourth institution, referred to as Bank C.

On January 3, 2019, AIM management met for dinner in Lubbock, Texas with the Chief Executive Officer and the President of Bank A. Shortly following the dinner meeting, the Chief Executive Officer of Bank A visited with representatives of Hillworth and indicated Bank A's interest in continuing to explore a potential business combination with AIM. In addition, following the dinner meeting, the Chief Executive Officer of Bank A invited AIM management to visit with Bank A's executive management team at Bank A's principal office.

On January 27 and 28, 2019, AIM management met separately with representatives of Bank B and Bank C. At these initial meetings, AIM management and representatives of Bank B and Bank C generally discussed their respective institutions, business plans and strategic objectives. At the conclusion of each meeting, it was agreed that representatives of Hillworth would follow up with both Bank B and Bank C to discuss their respective interests regarding a potential merger with AIM.

On January 28, 2019, AIM management met with representatives of Heartland. During this meeting, AIM management discussed AIM's recent performance and outlook for the future. Representatives from Heartland

discussed the Heartland organization generally, as well as Heartland's desire to continue to grow its banking presence in West Texas markets through strategic acquisitions. At the conclusion of the meeting, representatives of Heartland indicated that they would like AIM to consider Heartland in the event AIM decided to move forward with a potential business combination.

AIM met with the executive management team of Bank A at Bank A's principal office on February 22, 2019. After this meeting, Hillworth provided Bank A with preliminary economic analyses regarding a potential merger with AIM and communicated to Bank A's Chief Executive Officer the AIM board's expectations regarding the economic terms of a potential transaction. During the first and second quarters of 2019, Hillworth held multiple discussions with the Chief Executive Officer of Bank A in furtherance of a potential transaction, including discussions regarding proposed economic terms and deal metrics. Following these discussions, in June 2019, Bank A determined that it was in Bank's A best interest to cease discussions regarding a potential acquisition of AIM in order for Bank A to focus on completing its then-pending acquisition transactions. This would allow Bank A to integrate those acquisitions before making a determination regarding whether Bank A could meet AIM's expectations of the economic terms of a proposed transaction. Bank A indicated that it would revisit a potential transaction with AIM later in the year of 2019.

On February 28, 2019, AIM formally engaged Hillworth and Magstar Capital, LLC (“Magstar”) collectively to serve as AIM's exclusive financial advisor in the event AIM decided to pursue a transaction in which AIM would merge into an acquiror institution, as well as to explore potential merger opportunities with Heartland, Bank A, Bank B and Bank C. Hillworth, is an advisory firm specializing in community bank/banks holding companies, and Magstar is a registered FINRA-broker dealer that provides investment banking advisory services, of which Hillworth’s principals are registered representatives, and through which broker-dealer and investment banking services are provided.

On May 1, 2019, Hillworth visited with the Chief Executive Officer of Bank C. The Chief Executive Officer of Bank C requested financial analysis regarding a potential business combination with AIM, which was provided by Hillworth on May 3, 2019. On May 29, 2019, the Chief Executive Officer of Bank C communicated to Hillworth that Bank C would not be interested in pursuing a potential acquisition of AIM due to the geographic location of the AIM franchise in relation to Bank C's franchise footprint.

On May 13, 2019, representatives of Bank B met with representatives of AIM in Lubbock, Texas. After this meeting, AIM management directed Hillworth to request Bank B to execute a mutual non-disclosure agreement to allow preliminary due diligence investigations by both parties in order to continue to assess the viability of a potential merger. Hillworth granted Bank B and Bank B's investment bankers access to a virtual electronic data room for them to further evaluate a potential transaction with AIM. In the following weeks, Hillworth visited with Bank B to discuss deal consideration and communicate AIM's expectations. After further discussions, it was decided that representatives of Bank B would contact Hillworth later in 2019 if Bank B determined to pursue to a transaction with AIM.

On April 30, 2019, the Heartland board of directors held a regularly-scheduled meeting. At the meeting, members of Heartland's management reported on the status of discussions with AIM regarding a possible acquisition of AIM by Heartland. Management informed the board that an introductory in-person meeting had been held with AIM's management in January 2019, and that a second in-person meeting was expected to be held in the Summer of 2019. Heartland's management also provided the board with financial information regarding AIM and the general terms of a possible acquisition of AIM.

In early May 2019, representatives from Heartland contacted Hillworth to request a meeting with AIM management. This meeting was arranged for May 28, 2019 at AIM's principal office in Levelland, Texas. During this meeting, representatives of Heartland indicated Heartland's interest in being considered as a strategic merger partner for AIM if AIM's board of directors would be willing to consider an acquisition proposal from Heartland. AIM management indicated to Heartland that AIM was in discussions with another potential merger partner and that it would be appropriate for AIM and Heartland to follow up later in the Summer of 2019. The Heartland representatives also invited AIM management to visit with Heartland's executive management team at Heartland's headquarters in Dubuque, Iowa.

On June 28, 2019, AIM entered into a definitive agreement to acquire Union BancShares, Inc. and its wholly-owned subsidiary, FNB New Mexico. After this transaction was announced, representatives of Heartland contacted Hillworth and AIM management to congratulate them on the proposed acquisition. Heartland further

indicated that, because of Heartland's presence in New Mexico, AIM's expansion in New Mexico would make a potential business combination with AIM more attractive to Heartland. At this time, Heartland reiterated its invitation to host AIM management at its headquarters in Dubuque, Iowa. On August 26 and 27, 2019, with the assistance of Hillworth facilitating discussions between the parties, AIM management met with Heartland's executive management team in Dubuque, Iowa. As a condition precedent to attending this meeting, AIM requested a mutual non-disclosure agreement between AIM and Heartland, which was entered into on August 22, 2019.

On August 13, 2019, Heartland announced that it had signed a purchase and assumption agreement to acquire the assets of Rockford Bank & Trust Company, an Illinois state-chartered bank and wholly owned subsidiary of QCR Holdings, Inc.

Because AIM had not yet received any formal acquisition proposal from Heartland, Bank A, Bank B or Bank C, in furtherance of AIM's business plan and growth objectives, in August 2019, AIM management contacted two separate banking institutions (which are referred to herein as “Target A” and “Target B”), with which AIM management had long-established relationships, to ascertain whether or not either institution would be interested in considering an acquisition proposal from AIM. Both Target A and Target B expressed an interest in engaging in formal acquisition discussions with AIM. AIM promptly entered into non-disclosure agreements with both Target A and Target B, began receiving due diligence information from the parties and worked with respective advisors of the parties in preparing and negotiating proposed terms. On September 5, 2019, AIM executed a formal, non-binding indication of interest with the Target A, and on September 12, 2019 AIM executed a formal, non-binding indication of interest with Target B. In September and October of 2019, AIM conducted formal due diligence investigations of Target A and Target B and began negotiating definitive agreements with representatives of Target A and representatives of Target B.

On September 3, 2019, Heartland contacted Hillworth to request initial due diligence items on AIM to assist Heartland in formulating a formal merger proposal. AIM indicated to Heartland that AIM intended to continue pursuing its proposed acquisitions of Target A and Target B. Heartland nevertheless requested the opportunity to submit a formal acquisition proposal in writing, to which AIM agreed. In early October 2019, Hillworth established a virtual electronic data room and uploaded certain information regarding AIM for Heartland's preliminary due diligence investigation of AIM.

On October 6, 2019, AIM provided Heartland with access to an electronic virtual data room to allow Heartland to conduct a preliminary due diligence investigation of AIM. From October 6, 2019 through October 14, 2019, Heartland conducted due diligence regarding AIM's business, including its results of operations, financial condition, loan portfolio and tax, litigation and other matters. On October 14, 2019, Heartland's management developed a financial model containing proposed terms on which Heartland would consider acquiring AIM. In addition, Heartland's management prepared a term sheet for the acquisition to be reviewed by Heartland's board at its next regularly-scheduled meeting.

On October 21, 2019, Heartland's board held its regularly-scheduled quarterly meeting. At the meeting, Heartland management updated Heartland's board on the status of discussions with AIM. Management also presented its financial model for the acquisition of AIM and the proposed financial terms of such acquisition. After review of financial information and discussion with Heartland management, Heartland's board authorized the submission to AIM of a preliminary, non-binding term sheet providing for the merger of AIM with and into Heartland.

On October 23, 2019, Heartland provided Hillworth with an initial term sheet outlining the proposed terms by which Heartland would consider acquiring AIM. The term sheet provided for an aggregate merger consideration value range of $250 million to $260 million, consisting of 90% in shares of Heartland common stock and 10% in cash, in exchange for 100% of the outstanding capital stock and stock options of AIM.

On October 29, 2019, AIM met with representatives of Hillworth to discuss the proposed term sheet from Heartland. At this meeting, representatives of AIM informed Hillworth that Heartland's proposed merger consideration value range was less than the minimum merger consideration value that AIM's board expected in exchange for relinquishing AIM's independence. Hillworth subsequently responded to Heartland with AIM's expected range of merger consideration value.

On October 31, 2019, in light of the advance of discussions with Heartland, among other factors, AIM terminated discussions with Target B. Within a few weeks thereafter, AIM decided to defer discussions with Target A.

On November 12, 2019, Heartland's board held a special board meeting to discuss the proposed acquisition of AIM. At the meeting, Heartland's management reported on negotiations with AIM and provided an updated valuation of AIM and the proposed financial terms of a possible acquisition of AIM based on additional due diligence performed to date. After an in-depth discussion, Heartland's board of directors authorized management to deliver a formal, non-binding letter of intent to AIM proposing terms under which Heartland would acquire AIM.

On November 12, 2019, Heartland delivered to Hillworth a formal, non-binding letter of intent outlining the terms by which Heartland would propose to acquire AIM. The letter of intent indicated a proposal of 206.7028 shares of Heartland common stock and $684.88 in cash in exchange for each outstanding share of AIM common stock, providing for aggregate merger consideration of approximately 5,076,000 shares of Heartland common stock and approximately $16.8 million in cash, based on the number of outstanding shares of common stock of AIM as of September 30, 2019. In addition, Heartland offered to pay cash consideration to holders of AIM stock options in an amount based on the value of the price per share for AIM common stock in the transaction and the exercise price of the AIM stock options. The letter of intent also provided for a reduction, on a dollar-for-dollar basis, to the cash portion of the merger consideration to the extent that AIM's adjusted tangible common equity at closing was less than $148.0 million, and an increase, on a dollar-for-dollar basis, to the cash portion of the merger consideration to the extent that AIM's adjusted tangible common equity at closing was greater than $149.0 million, subject to a maximum increase of $5.0 million. The letter of intent included an exclusivity period of 60 days to allow the parties to conduct reciprocal due diligence investigations and negotiate the definitive agreement.

On November 19, 2019, AIM's board of directors met with representatives of Hillworth. At this meeting, Hillworth provided the AIM board of directors with its analyses of the financial terms of the Heartland offer as set forth in the letter of intent. As part of its evaluation of the Heartland offer, the AIM board of directors considered, among other factors, the financial, business and legal terms of the letter of intent, historical payments and rates of cash and stock dividends on outstanding common stock of Heartland, historical trading multiples and performance of Heartland's common stock, the timetable for completing the proposed transaction and exclusivity period proposed by Heartland, and the potential economies of scale and increased efficiencies of operations that could result from a combination with Heartland. After due consideration of these and other factors, and further deliberations, the AIM board of directors unanimously determined that it was advisable and in the best interest of AIM and its shareholders to execute the Heartland letter of intent and pursue a transaction with Heartland generally based on the terms of the letter of intent, subject to Heartland agreeing to a few changes to the letter of intent, which Hillworth negotiated with Heartland.

On November 21, 2019, Heartland provided a revised letter of intent, which incorporated most of the changes that AIM and Hillworth had requested. The revised letter of intent provided for merger consideration of 207.0 shares of Heartland common stock and $685.00 in cash in exchange for each outstanding share of AIM common stock, providing for aggregate merger consideration of approximately 5,083,000 shares of Heartland common stock and approximately $16.8 million in cash, based on the number of outstanding shares of common stock of AIM as of September 30, 2019. Based on Heartland's closing stock price of $47.21 per share on November 19, 2019, three days prior to the date of the letter of intent, the merger consideration would have a value of approximately $256.8 million, or $10,457 per share of AIM common stock. The revised letter of intent also provided that Heartland would pay cash consideration to holders of AIM stock options in an amount based on the value of the price per share for AIM common stock in the transaction and the exercise price of the AIM stock options, providing for aggregate consideration of approximately $9.8 million to the option holders. The letter of intent provided for a reduction, on a dollar-for-dollar basis, to the cash portion of the merger consideration to the extent that AIM's adjusted tangible common equity at closing was less than $145.0 million, and an increase, on a dollar-for-dollar basis, to the cash portion of the merger consideration to the extent that AIM's adjusted tangible common equity at closing was greater than $148.0 million, subject to a maximum increase of $5.0 million. The letter of intent included an exclusivity period of 60 days to allow the parties to conduct reciprocal due diligence investigations and negotiate the definitive agreement.

On November 22, 2019, after further review of the revised letter of intent by AIM management and Hillworth, AIM signed and delivered the revised letter of intent to Heartland.

Upon the execution of the letter of intent, Hillworth expanded the contents of the virtual electronic data room to facilitate due diligence investigations by both of the parties. From November 24, 2019 through February 10, 2020, Heartland and AIM conducted reciprocal due diligence on each organization's businesses, including with respect to regulatory, litigation, tax, financial and other matters.

On November 30, 2019, Heartland announced that it had completed its acquisition of the assets of Rockford Bank & Trust Company.

On December 10, 2019, Heartland's board of directors held a special meeting. At the meeting, Heartland management updated the board on the status of Heartland's due diligence investigation of AIM. Heartland's board directed management to continue negotiations with AIM and submit a draft merger agreement to AIM.

AIM received the initial draft of the merger agreement from Heartland on December 20, 2019, and the parties negotiated the terms of the merger agreement until the document was executed on February 11, 2020.

On January 28, 2020, AIM's financial advisor, Hillworth, and AIM's legal counsel, Fenimore, Kay, Harrison & Ford, LLP, conducted a reverse due diligence conference call with senior management of Heartland covering, among other topics, Heartland's corporate strategy, credit quality and loan portfolio trends, financial performance for 2019 and key assumptions related to Heartland's projected performance and earnings, certain operational matters and regulatory compliance and legal matters.

On February 10, 2020, AIM's board of directors met with its financial advisor to discuss the merger agreement, which was in its substantially final form. The AIM board of directors heard a presentation from representatives of Magstar on the financial aspects of the transaction. Also at this meeting, representatives of Magstar reviewed certain other material terms of the merger agreement and ancillary legal documents to the merger agreement, including the provisions of the merger agreement that permit the AIM board to terminate the merger agreement under certain circumstances in order for the AIM board to comply with its fiduciary duties as directors of AIM. Magstar also reviewed in detail the business points, contingencies and timing considerations related to the merger. The AIM board of directors asked a series of questions to the Magstar representatives regarding the terms and conditions of the merger agreement and engaged in a full discussion regarding the proposed transaction. At the conclusion of this discussion and after responding to questions from the directors, Magstar rendered to the AIM board of directors its oral opinion that, subject to the assumptions, limitations and qualifications set forth in the opinion, the aggregate merger consideration to be received by shareholders of AIM from Heartland in the merger, which consisted of 207.0 shares of Heartland common stock and $685.00 in cash for each outstanding share of AIM common share, along with a cash value to AIM option holders based on the per share value of the merger consideration to AIM shareholders and the exercise price of the options, subject to adjustment as provided in the merger agreement, was fair to the shareholders of AIM, from a financial point of view. Magstar's oral opinion was subsequently confirmed by delivery of its written opinion, dated February 10, 2020, to the AIM board of directors. The AIM board of directors asked a series of questions to AIM's advisors regarding the terms and conditions of the merger agreement and engaged in a full discussion regarding the proposed transaction.

Based upon the AIM board's review and discussion of the merger agreement, the opinion of AIM's financial advisor and other relevant factors, the AIM board of directors unanimously approved the merger agreement, the merger and the other transactions contemplated by the merger agreement, and authorized AIM's management to execute and deliver the merger agreement.

On February 11, 2020, the trustees of the AIM Bancshares, Inc. 401(k) and Employee Stock Ownership Plan, dated January 1, 2007, as amended (the “KSOP”), received an opinion from an independent valuation firm stating that (i) the consideration to be received by the KSOP pursuant to the merger agreement for the shares of AIM common stock held by the KSOP is not less than the “adequate consideration” (as defined in Section 3(18) of ERISA) of such shares, and (ii) the terms and conditions of the merger agreement, taken as a whole, are in the best interest of the KSOP from a financial point of view.

On February 11, 2020, Heartland's board of directors held a special meeting to review and discuss the proposed merger and the merger agreement. At this meeting, Heartland's board of directors received presentations from Heartland's executive management (including its General Counsel) regarding the terms of the

merger agreement and strategic and financial considerations relating to the merger. Heartland's financial advisor, Stephens Inc. (“Stephens”), discussed financial aspects of the proposed transaction, and Stephens rendered an oral opinion (subsequently confirmed in writing) to Heartland's board of directors to the effect that, as of that date and subject to the procedures followed, assumptions made, matters considered, and qualifications and limitations on the review undertaken by Stephens as set forth in such opinion, the merger consideration in the merger was fair to Heartland from a financial point of view. Heartland's board of directors asked a number of questions of management and Stephens regarding the terms and conditions of the merger agreement and the strategic and economic aspects of the merger and engaged in a full discussion regarding the proposed transaction. Following this discussion, Heartland's board of directors unanimously voted to approve the merger agreement and the transactions contemplated by the merger agreement, including the merger, and authorized Heartland's management to execute the merger agreement.

On February 11, 2020, AIM and Heartland executed the merger agreement, and certain directors and executive officers of AIM and AimBank delivered to Heartland the shareholder voting agreement. Heartland announced the transaction after the close of trading on the NASDAQ Stock Exchange on February 11, 2020.

After careful consideration, at its meeting on February 10, 2020, the AIM board determined that the merger was in the best interests of AIM and its shareholders and that the consideration to be received in the merger was fair to the AIM shareholders. Accordingly, the AIM board unanimously approved the merger agreement and recommends that the AIM shareholders vote “FOR” the AIM merger proposal.

In reaching its decision to approve the merger agreement and recommend the merger proposal to its shareholders, the AIM board evaluated the merger and the merger agreement, in consultation with AIM's management, as well as its legal and financial advisors, and considered a number of positive factors, including the following material factors, which are not presented in order of priority:

The AIM board also considered potential risks and potential negative factors concerning the merger in connection with its deliberations of the proposed transaction, including the following material factors:

The foregoing discussion of the factors considered by the AIM board is not intended to be exhaustive, but is believed to include the material factors considered by the AIM board. The AIM board collectively reached the unanimous conclusion to approve the merger agreement and the merger in light of the various factors described above and other factors that each member of the AIM board determined was appropriate. In view of the wide variety of the factors considered in connection with its evaluation of the merger and the complexity of these matters, the AIM board did not find it useful, and did not attempt, to quantify, rank or otherwise assign relative weights to these factors. In considering the factors described above, the individual members of the AIM board may have given different weight to different factors. The AIM board conducted an overall analysis of the factors described above (which included thorough discussions with AIM management and AIM's advisors), and considered the factors overall to be favorable to, and to support, its determination. It should be noted that this explanation of the AIM board's reasoning and all other information presented in this section is forward-looking in nature and, therefore, should be read in light of the factors discussed under the heading “Forward-Looking Statements.”

The AIM board of directors unanimously recommends that you vote “FOR” the merger proposal.

The fairness opinion and a summary of the underlying financial analyses of AIM's financial advisor is described below. The description contains projections, estimates and other forward-looking statements about the future earnings or other measures of the future performance of AIM. The projections were based on numerous variables and assumptions, which are inherently uncertain, including factors related to general economic and competitive conditions. Accordingly, actual results could vary significantly from those set forth in the projections. You should not rely on any of these statements as having been made or adopted by AIM or Heartland. You should review the copy of the fairness opinion, which is attached as Appendix C.

Magstar acted as AIM’s financial advisor in connection with the proposed merger. Magstar is a nationally recognized investment banking firm with substantial experience in transactions similar to the merger and is familiar with AIM and its operations. As part of its investment banking business, Magstar is continually engaged in the valuation of businesses and their securities in connection with, among other things, mergers and acquisitions.

Magstar reviewed the financial aspects of the proposed merger with AIM’s board of directors and, on February 10, 2020, delivered a written opinion to AIM’s board of directors that, subject to the review, assumptions and limitations set forth in the opinion, the merger consideration to be received by the shareholders of AIM in the merger was fair to the shareholders of AIM from a financial point of view. In requesting Magstar’s advice and opinion, no limitations were imposed by AIM upon Magstar with respect to the investigations made or procedures followed by Magstar in rendering its opinion.

The full text of Magstar's written opinion is included in this proxy statement/prospectus as Appendix C and is incorporated herein by reference. You are urged to read the opinion in its entirety for a description of the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken by Magstar. The summary of Magstar's opinion included in this proxy statement/prospectus is qualified in its entirety by reference to the full text of such opinion. Magstar's opinion was directed to AIM's board of directors and addresses only the fairness of the merger consideration to be paid to AIM shareholders in connection with the merger. Magstar did not opine on any individual stock, cash, or other components of consideration payable in connection with the merger. Magstar's opinion does not address the underlying business decision to proceed with the merger and does not constitute a recommendation to any of the shareholders as to how such shareholder should vote at the AIM annual meeting on the merger or any related matter.

During the course of its engagement and for the purposes of the opinion set forth herein, Magstar:

Magstar assumed, without investigation, that there have been, and from the date hereof through the effective date of the merger there will be, no material changes in the financial condition and results of operations of AIM, AimBank, Heartland, or FB&T since the date of the latest financial information described above. Magstar relied, without independent verification or investigation, on the assessments of the management of AIM, AimBank, Heartland, or FB&T as to their existing and future relationships with key employees and partners, clients, products and services, and Magstar assumed that there will be no developments with respect to any such matters that would affect Magstar's analyses or opinion. Magstar further assumed, without independent verification, that the representations and financial and other information included in the merger agreement and all other related documents and instruments that are referred to therein or otherwise provided to Magstar by AIM, AimBank, Heartland, or FB&T are true and complete. Magstar relied upon the management of AIM, AimBank, Heartland, or FB&T as to the reasonableness and achievability of the financial forecasts, and projections, estimates and other forward-looking information (including the Synergies) provided to Magstar by AIM, AimBank, Heartland, or FB&T, and Magstar assumed such forecasts, projections, estimates and other forward-looking information (including the Synergies) have been reasonably prepared by AIM, AimBank, Heartland, or FB&T on a basis reflecting the best currently available information and AIM's, AimBank's, Heartland's, or FB&T's judgments and estimates. Magstar assumed that such forecasts, projections, estimates and other forward-looking information (including the Synergies) would be realized in the amounts and at the times contemplated thereby, and Magstar

did not, in any respect, assume any responsibility for the accuracy or reasonableness thereof. Magstar has been authorized by AIM and AimBank to rely upon such forecasts, projections, estimates and other information and data, and Magstar expressed no view as to any such forecasts, projections, estimates or other forward-looking information or data, or the bases or assumptions on which they were prepared.

In performing its review, Magstar assumed and relied upon the accuracy and completeness of all of the financial and other information that was available to Magstar from public sources, that was provided to Magstar by AIM, AimBank, Heartland, and FB&T or their respective representatives or that was otherwise reviewed by Magstar for purposes of rendering the opinion. Magstar further relied on the assurances of the respective management of AIM, AimBank, Heartland, and FB&T and that they are not aware of any facts or circumstances that would make any of such information inaccurate or misleading. Magstar has not been asked to and has not undertaken an independent verification of any of such information, and Magstar has not assumed any responsibility or liability for the accuracy or completeness thereof. Magstar assumed that each party to the merger agreement would advise Magstar promptly if any information previously provided to Magstar became inaccurate or was required to be updated during the period of Magstar's review.

Magstar is not an expert in the evaluation of loan and lease portfolios for purposes of assessing the adequacy of the allowances for losses with respect thereto. Magstar assumed that such allowances for AIM, AimBank, Heartland and FB&T are, in the aggregate, adequate to cover such losses and will be adequate on a pro forma basis for the combined entity. Magstar was not requested to make, and did not make, an independent evaluation, physical inspection or appraisal of the assets, properties, facilities, or liabilities (contingent or otherwise) of AIM, AimBank, Heartland and FB&T, the collateral securing any such assets or liabilities, or the collectability of any such assets, and Magstar was not furnished with any such evaluations or appraisals; nor did Magstar review any loan or credit files of AIM, AimBank, Heartland and FB&T.

Magstar did not evaluate the solvency of AIM, AimBank, Heartland, or FB&T, under any state or federal law relating to bankruptcy, insolvency or similar matters. Accordingly, Magstar expressed no opinion regarding the liquidation value of AIM, AimBank, Heartland, or FB&T, or any other entity. Magstar has also assumed that AIM, AimBank, Heartland, and FB&T would remain as a going concern for all periods relevant to Magstar's analysis. Accordingly, Magstar expressed no opinion with respect to the foregoing. Further, without limiting the generality of the foregoing, Magstar has not undertaken an independent analysis of any pending or threatened litigation, regulatory action, possible unasserted claims or other contingent liabilities to which AIM, AimBank, Heartland, or FB&T is a party or may be subject, and Magstar's opinion makes no assumption concerning, and therefore does not consider, the possible assertion of claims, outcomes or damages arising out of any such matters. Magstar has also assumed that neither AIM, AimBank, Heartland, nor FB&T is a party to any material pending transaction, including without limitation any financing, recapitalization, acquisition or merger, divestiture or spin-off, other than the merger contemplated by the merger agreement.

Magstar relied upon and assumed, with AIM’s consent and without independent verification, that the merger will be consummated substantially in accordance with the terms set forth in the merger agreement, without any waiver of material terms or conditions by AIM, Heartland, or any other party to the merger agreement and that the final agreement will not differ materially from the draft Magstar reviewed. Magstar assumed that the merger will be consummated in compliance with all applicable laws and regulations. AIM advised Magstar that they were not aware of any factors that would impede any necessary regulatory or governmental approval of the merger. Magstar assumed that the necessary regulatory and governmental approvals as granted would not be subject to any conditions that would be unduly burdensome on AIM, AimBank, Heartland or FB&T, or would have a material adverse effect on the contemplated benefits of the merger. Magstar further assumed that the merger will qualify as a tax-free reorganization for United States federal income tax purposes.

Magstar’s opinion does not consider, include or address: (i) any legal, tax, accounting, or regulatory consequences of the merger on AIM, Heartland or their respective shareholders; (ii) any advice or opinions provided by any other advisor to the Board of Directors of AIM or Heartland; (iii) any other strategic alternatives that might be available to AIM; or (iv) whether Heartland has sufficient cash or other sources of funds to enable it to pay any consideration contemplated by the Merger.

In performing its analyses, Magstar made numerous assumptions with respect to industry performance, general business, economic, market and financial conditions and other matters, many of which are beyond the control of Magstar, AIM, AimBank, Heartland and FB&T. Magstar's opinion was necessarily based on financial,

economic, market and other conditions and circumstances as they existed on, and on the information made available to Magstar as of, the dates used in its opinion. Any estimates contained in the analyses performed by Magstar are not necessarily indicative of actual values or future results, which may be significantly more or less favorable than suggested by these analyses. Additionally, estimates of the value of businesses or securities do not purport to be appraisals or to reflect the prices at which such businesses or securities may be sold or the prices at which any securities may trade at any time in the future. Accordingly, these analyses and estimates are inherently subject to substantial uncertainty. Magstar's opinion does not address the relative merits of the merger as compared to any other business combination in which AIM might engage. In addition, Magstar's fairness opinion was among several factors taken into consideration by AIM's board of directors in making its determination to approve the merger agreement and the merger. Consequently, the analyses described below should not be viewed as solely determinative of the decision of AIM's board of directors or AIM's management with respect to the fairness of the merger consideration to be received by AIM's shareholders in connection with the merger.

Magstar’s opinion was based solely upon the information available to Magstar and described above, and the economic, market and other circumstances as they existed as of the date thereof. Events occurring and information that becomes available after the date thereof could materially affect the assumptions and analyses used in preparing its opinion. Magstar has not undertaken to update, revise, reaffirm or withdraw its opinion or to otherwise comment upon events occurring or information that becomes available after the date thereof.

In arriving at its opinion, Magstar did not attribute any particular weight to any single analysis or factor considered by it, but rather made qualitative judgments as to the significance and relevance of each analysis and factor. Accordingly, Magstar believes that its analyses must be considered as a whole and that selecting portions of its analyses, without considering all analyses, would create an incomplete view of the process underlying its opinion.

The following is a summary of the material analyses prepared by Magstar and delivered to AIM's board of directors on February 10, 2020, in connection with the delivery of its fairness opinion. This summary is not a complete description of the analyses underlying the fairness opinion or the presentation prepared by Magstar, but it summarizes the material analyses performed and presented in connection with such opinion. The preparation of a fairness opinion is a complex analytical process involving various determinations as to the most appropriate and relevant methods of financial analysis and the application of those methods to the particular circumstances of the contemplated merger. Therefore, a fairness opinion is not readily susceptible to partial analysis or summary description. In arriving at its opinion, Magstar did not attribute any particular weight to any analysis or factor that it considered, but rather made qualitative judgments as to the significance and relevance of each analysis and factor. The financial analyses summarized below include information presented in tabular format. The analyses and the summary of the analyses must be considered as a whole and selecting portions of the analyses and factors or focusing on the information presented below in tabular format, without considering all analyses and factors or the full narrative description of the financial analyses, including the methodologies and assumptions underlying the analyses, could create a misleading or incomplete view of the process underlying the analyses and opinion of Magstar. The tables alone are not a complete description of the financial analyses. For purposes of the analysis, deal value is comprised of the merger consideration plus option consideration.

Market Approach – Comparable Transactions. As part of its analysis, Magstar reviewed publicly available information related to two comparable groups (a “Regional Group” and a “Nationwide Group”) of select acquisition transactions of banks. The Regional Group consisted of acquisition transactions of banks in the Southern Region of the United States (consisting of the states of Alabama, Arkansas, Colorado, Florida, Georgia, Louisiana, Mississippi, North Carolina, New Mexico, Oklahoma, South Carolina, Tennessee, Texas, Utah, Virginia, and West Virginia) in Non-Major Metropolitan Statistical Areas (“MSAs”), defined as MSAs with a population of less than 2 million, announced since January 1, 2013, in which the targets' total assets were between $500 million and $5.0 billion, last-twelve-months (“LTM”) return on average assets (“ROAA”) was more than 0.90%, tangible common equity to tangible assets (“TE/TA”) was less than 15.0%, and nonperforming assets were less than 2.0% of total assets. The Nationwide Group consisted of acquisition transactions of banks in the United States announced since January 1, 2018, in which the targets ' total assets were between $1.0 billion and $3.0 billion, LTM ROAA was between 0.75% and 2.0%, and nonperforming assets were less than 1.0% of total assets. In each case, for which financial information was available, no transaction that fit the

selection criteria was excluded. Information for the target institutions was based on balance sheet data as of, and income statement data for the twelve months preceding the most recent quarter prior to announcement of the transactions. The resulting two groups consisted of the following transactions (18 transactions for the Regional Group and 10 transactions for the Nationwide Group):

For each precedent transaction, Magstar compared the implied ratio of deal value to certain financial characteristics of AIM as follows:

The results of the analysis are set forth in the table below. Transaction multiples for the merger were based on the deal value assumed by Magstar of $279,589,828 for AIM and were based on December 31, 2019 financial results of AIM.

Using publicly available information, Magstar compared the financial performance of AIM with that of the median of the precedent transactions from both the Regional and Nationwide Groups. The performance highlights are based on December 31, 2019 financial results of AIM.

No company or transaction used as a comparison in the above transaction analyses is identical to AIM, and no transaction was consummated on terms identical to the terms of the merger agreement. Accordingly, an analysis of these results is not strictly mathematical. Rather, it involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies. The resulting median values of the Precedent Transactions Regional Group using the median values indicated an implied aggregate valuation ranging between $244.4 million and $334.6 million compared to the estimated deal value of $279.6 million. The resulting median values of the Precedent Transactions Nationwide Group using the median values indicated an implied aggregate valuation ranging between $232.4 million and $327.8 million compared to the estimated deal value of $279.6 million.

Income Approach – Discounted Cash Flow Analysis. Taking into account various factors including, but not limited to, AIM's recent performance, the current banking environment and the local economy in which AIM operates, Magstar determined, in consultation with and based on information provided by management of AIM, earnings estimates for AIM over a forward looking five year period, and AIM management developed the forward-looking projections and key assumptions, which formed the basis for the discounted cash flow analyses. The resulting projected net income numbers used for the analysis were $24.8 million for 2020, $26.6 million for 2021, $28.0 million for 2022, $29.5 million for 2023, $31.1 million for 2024, and $32.7 million for 2025.

To determine present values of AIM based on these projections, Magstar utilized three discounted cash flow models, each of which capitalized terminal values using a different methodology: (a) Perpetuity Model (“DCF

Present Value of Future Free Cash Flow”); (b) Terminal Price/Earnings Multiple (“DCF Terminal P/E Multiple”); and (c) Terminal Price/Tangible Book Value Multiple (“DCF Terminal P/TBV Multiple”).

In the DCF Present Value of Future Free Cash Flow analysis, a perpetuity model was used assuming AIM's assets increase perpetually at an annual growth rate of 2.0%. The terminal value was then calculated assuming a range of discount rates between 11.0% and 15.0%, with a midpoint of 13.0%. The resulting aggregate values of AIM's present value of future free cash flows ranged between $235.8 million and $335.8 million, with a midpoint of $279.5 million.

In the DCF Terminal P/E Multiple analysis, an estimated value of AIM's common stock was calculated based on the present value of AIM's after-tax net income based on AIM management's forward-looking projections. Magstar utilized a terminal value at the end of 2025 by applying a range of price-to-earnings multiples of 13.7x to 17.7x, with a midpoint of 15.7x, which is based around the median price-to-earnings multiple derived from transactions in the Nationwide Group. The present value of AIM's projected dividends, plus the terminal value was then calculated assuming a range of discount rates between 11.0% and 15.0%, with a midpoint of 13.0%. This range of discount rates was chosen to reflect different assumptions regarding the required rates of return of holders or prospective buyers of AIM's common stock. The resulting aggregate values of AIM's common stock of the DCF Terminal P/E Multiple ranged between $237.8 million and $288.9 million, with a midpoint of $261.9 million.

In the DCF Terminal P/TBV Multiple analysis, the same earnings estimates and projected net income were used as in the preceding DCF Terminal P/E Multiple analysis, however, in arriving at the terminal value at the end of 2025, Magstar applied a range of price-to-tangible book value multiples of 1.64x to 1.84x with the midpoint being 1.74x, which is based around the median price-to-tangible book value multiple derived from transactions in the Nationwide Group. The present value of projected dividends, plus the terminal value, was then calculated assuming a range of discount rates between 11.0% and 15.0%, with a midpoint of 13.0%. The resulting aggregate values of AIM's common stock of the DCF Terminal P/TBV Multiple ranged between $252.4 million and $306.6 million, with a midpoint of $278.0 million.

These analyses and their underlying assumptions yielded a range of implied multiple values for AIM, which are outlined in the table below:

Magstar noted that while the discounted cash flow present value analysis is a widely used valuation methodology, it relies on numerous assumptions, including asset and earnings growth rates, projected dividend payouts, terminal values and discount rates. Magstar's analysis does not purport to be indicative of the actual values or expected values of AIM's common stock.

Heartland Comparable Companies Analysis. Magstar used publicly available information to compare selected financial and trading information for Heartland and a group of 11 publicly-traded financial institutions selected by Magstar which was based on publicly-traded banks in the United States with total assets between $10.0 billion and $15.0 billion, LTM ROAA between than 1.0% and 1.5%, and traded on a major exchange. The following publicly-traded financial institutions comprised the comparable peer group:

The analysis compared publicly available financial and market trading information for Heartland and the data for the 11 financial institutions identified above as of and for the most recent twelve-month period which was publicly available. The table below compares the data for Heartland and the median data for the 11 financial institutions identified above, with pricing data as of February 7, 2020:

Heartland fell within the range of pricing metrics of comparable companies. No company used as a comparison in the above analyses is identical to Heartland. Accordingly, an analysis of these results is not strictly mathematical. Rather, it involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies.

AIM Comparable Companies Analysis. Magstar compared selected financial information and the deal value of AIM to selected publicly available financial and trading information for a group of 10 publicly-traded financial institutions selected by Magstar which was based on publicly-traded banks in the Southwest United States with total assets between $1.0 billion and $5.0 billion, LTM ROAA between 0.5% and 1.5%, and traded on a major exchange. The following publicly-traded financial institutions comprised the comparable peer group:

The analysis compared selected financial information and the deal value of AIM to the selected publicly available financial and market trading information for the 10 financial institutions identified above as of and for the most recent twelve-month period which was publicly available. The table below compares the data for AIM and the median data for the 10 financial institutions identified above, with pricing data as of February 7, 2020:

The estimated deal value to AIM fell within the range of pricing metrics of comparable companies. No company used as a comparison in the above analyses is identical to AIM. Accordingly, an analysis of these results is not strictly mathematical. Rather, it involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies.

Accretion / Dilution Analysis. Magstar performed pro forma merger analyses that combined projected income statement and balance sheet information of AIM and Heartland. Assumptions regarding the accounting treatment, acquisition adjustments and cost savings were used to calculate the financial impact that the merger would have on certain projected financial results of Heartland. In the course of this analysis, Magstar used the median S&P CapIQ mean consensus estimates for earnings estimates for Heartland for the years ending December 31, 2020 and December 31, 2021 and used earnings estimates provided by AIM's management for AIM for the years ending December 31, 2020 and December 31, 2021. This analysis indicated that the merger is expected to be dilutive to Heartland's consensus estimated earnings per share in 2020 and accretive to Heartland's estimated earnings per share in 2021. The analysis also indicated that the merger is expected to be dilutive to tangible book value per share for Heartland in 2020 and 2021 and that Heartland would maintain

capital ratios in excess of those required for Heartland to be considered well-capitalized under existing regulations. For all of the above analyses, the actual results achieved by AIM and Heartland prior to and following the merger will vary from the projected results, and the variations may be material.

Other Factors and Analyses. Magstar took into consideration various other factors and analyses, including but not limited to: current market environment; merger and acquisition environment; movements in the common stock valuations of selected publicly-traded banking companies; and movements in the S&P 500 Index.

Magstar's Relationship. AIM engaged Hillworth and Magstar on February 28, 2019 to serve collectively as AIM's exclusive financial advisor in connection with the proposed merger and to issue a fairness opinion to AIM's board of directors in connection with the proposed merger. AIM understands that Hillworth is an advisory services firm that provides services that do not require it to register as a broker-dealer with the Financial Industry Regulatory Authority (“FINRA”), the SEC or U.S. state regulators. Any services in connection with this merger that were required to be performed by or through a registered broker-dealer were performed by Magstar (Member FINRA/SIPC), through the employees of Magstar and employees of Hillworth that are registered representatives of Magstar.

Pursuant to the terms of the engagement agreement, at the time the merger is completed, AIM will pay Magstar a completion fee of 1.0% of the aggregate purchase consideration in the merger, which payment is contingent upon the completion of the merger. Magstar received a $250,000 fee upon rendering its fairness opinion to the AIM board of directors, which opinion fee will be credited in full toward the completion fee that will become payable to Magstar at the time the merger is completed. Pursuant to the engagement agreement, in addition to its fees and regardless of whether the merger is consummated, AIM has agreed to reimburse Magstar for certain reasonable out-of-pocket expenses incurred by Magstar in performing its services and to indemnify Magstar and its affiliates against certain claims, losses and expenses arising out of the merger or Magstar's engagement.

In the two years preceding the date of its opinion, Hillworth and Magstar provided certain financial advisory services to AIM and received customary compensation for such services. Affiliates and employees of Hilworth hold investments in AIM, which has been disclosed to AIM. Magstar or its affiliates, as well as Hillworth (whose principals are registered with Magstar) may presently or in the future seek or receive compensation from AIM or Heartland in connection with future transactions, or in connection with potential advisory services and corporate transactions, although to Magstar’s knowledge none are expected at this time. Except for the foregoing, during the two years preceding the date of this opinion there have not been, and there currently are no mutual understandings contemplating in the future, any material relationships between Magstar and AIM or Heartland.

Conclusion. Based upon the foregoing analyses and other investigations and assumptions set forth in its opinion, without giving specific weightings to any one factor, analysis or comparison, Magstar determined that, subject to the review, assumptions and limitations set forth in the opinion, the merger consideration to be paid in connection with the merger is fair from a financial point of view to AIM’s shareholders. Each shareholder is encouraged to read Magstar’s fairness opinion in its entirety. The full text of this fairness opinion is included as Appendix C to this proxy statement/prospectus.

AIM does not as a matter of course make public projections as to future performance, revenues, earnings or other financial results due to, among other reasons, the uncertainty of the underlying assumptions and estimates. However, AIM is including in this document certain unaudited prospective financial information that was made available to AIM's financial advisor in connection with the merger. The inclusion of this information should not be regarded as an indication that any of AIM, Magstar or Heartland or any of their respective representatives considered, or now considers, the information to be necessarily predictive of actual future results.

This information, which was prepared by management of AIM, was prepared solely for internal use and is subjective in many respects. The unaudited prospective financial information reflects numerous estimates and assumptions made with respect to business, economic, market, competition, regulatory and financial conditions and matters specific to the business of AIM, all of which are difficult to predict and many of which are beyond the control of AIM. The unaudited prospective financial information reflects assumptions as to certain business decisions that are subject to change and, in many respects, subjective judgment, and thus is susceptible to multiple interpretations and periodic revisions based on actual experience and business developments. AIM can

give no assurance that the unaudited prospective financial information and the underlying estimates and assumptions will be realized. In addition, because the unaudited prospective financial information covers multiple years, the information by its nature becomes less predictive with each successive year. Actual results may differ materially from those set forth below, and important factors that may affect actual results and cause the unaudited prospective financial information to be inaccurate include, but are not limited to, risks and uncertainties relating to the business of AIM, industry performance, general business and economic conditions, customer requirements, competition and adverse changes in applicable laws, regulations or policies. For other factors that could cause actual results to differ, see the sections titled “Risk Factors” and “Forward-Looking Statements.”

The unaudited prospective financial information was not prepared with a view toward public disclosure, nor was it prepared with a view toward compliance with GAAP, published guidelines of the SEC or the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial information. In addition, the unaudited prospective financial information requires significant estimates and assumptions that make it inherently less comparable to the similarly titled GAAP measures in the historical GAAP financial statements of AIM. Neither AIM's independent accountants, nor any other independent accountants, have compiled, examined or performed any procedures with respect to the unaudited prospective financial information shown below, nor have they expressed any opinion or any other form of assurance on such information or its achievability.

Furthermore, the unaudited prospective financial information does not take into account any circumstances or events occurring after the date it was prepared. AIM can give no assurance that, had the unaudited prospective financial information been prepared either as of the date of the reorganization agreement or as of the date of this proxy statement/prospectus, similar estimates and assumptions would be used. AIM does not intend to, and disclaims any obligation to, make publicly available any update or other revision to the unaudited prospective financial information to reflect circumstances existing since their preparation or to reflect the occurrence of unanticipated events, even in the event that any or all of the underlying assumptions are shown to be in error, or to reflect changes in general economic or industry conditions. The unaudited prospective financial information does not take into account the possible financial and other effects on either Heartland or AIM, as applicable, of the merger and does not attempt to predict or suggest future results of the combined company. The unaudited prospective financial information does not give effect to the impact of negotiating or executing the reorganization agreement, the expenses that may be incurred in connection with consummating the merger, the potential synergies that may be achieved by the combined company as a result of the merger, the effect of any business or strategic decision or action that has been or will be taken as a result of the reorganization agreement having been executed, or the effect on either AIM or Heartland, as applicable, of any business or strategic decisions or actions that would likely have been taken if the reorganization agreement had not been executed, but which were instead altered, accelerated, postponed or not taken in anticipation of the merger. Further, the unaudited prospective financial information does not take into account the effect on either Heartland or AIM, as applicable, of any possible failure of the merger to occur. None of Heartland, AIM or Magstar or their respective affiliates, officers, directors, advisors or other representatives has made, makes or is authorized in the future to make any representation to any shareholder of AIM or Heartland, or any other person, regarding AIM's actual performance compared to the information contained in the unaudited prospective financial information or that the projected results will be achieved. The inclusion of the unaudited prospective financial information should not be deemed an admission or representation by AIM or Heartland that it is viewed as material information of AIM, particularly in light of the inherent risks and uncertainties associated with such forecasts. The summary of the unaudited prospective financial information included below is not being included to influence your decision whether to vote for the merger and the transactions contemplated in connection with the merger, but is being provided solely because it was made available to AIM's financial advisor in connection with the merger.

In light of the foregoing, and considering that the annual meeting of shareholders of AIM will be held several months after the unaudited prospective financial information was prepared, as well as the uncertainties inherent in any forecasted information, shareholders of AIM are cautioned not to place unwarranted reliance on such information in connection with their consideration of the merger.

The following table presents selected unaudited prospective financial data of AIM for the years ending December 31, 2020, 2021 and 2022:

As part of Heartland's business strategy, Heartland regularly evaluates opportunities to acquire bank holding companies, banks and other financial institutions. In reaching its conclusion to adopt and approve the merger agreement, Heartland's board of directors evaluated the merger in consultation with Heartland's financial and legal advisors.

Heartland's board of directors approved the merger because:

In considering the recommendation of the AIM board of directors to approve and adopt the merger agreement, you should be aware that AIM's directors and executive officers have financial interests in the merger that are different from, or in addition to, the interests of AIM shareholders generally. These financial interests are described below. The AIM board of directors was aware of these interests and considered them, among other matters, in approving the merger agreement and the transactions contemplated by the merger agreement.

Treatment of AIM Stock Options. The merger agreement provides that, at the effective time of the merger, each AIM stock option outstanding and unexercised immediately prior to the effective time of the merger will be cancelled in exchange for the right to receive a cash payment equal to the product of (a) the number of shares of AIM common stock subject to such AIM stock option, and (b) the excess of (i) an amount determined by (A) multiplying 207.0 by the volume-weighted average trading prices for the Heartland common stock for each of the fifteen (15) consecutive trading days ending on and including the trading day immediately preceding the fifth business day preceding the closing date, rounded to three decimal places, as quoted on the NASDAQ Global Select Market on such trading day plus (B) $685.00 (subject to adjustment as described below), less (ii) the exercise price per share of such AIM stock option (the amount determined by the foregoing formula, the “option consideration”), minus any applicable taxes required to be withheld. If the option consideration for any AIM stock option is a negative number, the holder of the stock option will not be entitled to any such cash payment.

Wade Employment Agreement. Heartland, FB&T, AIM and AimBank have executed an employment agreement with Mr. Scott Wade that will become effective upon completion of the merger (the “Wade employment agreement”). The Wade employment agreement provides that Mr. Wade will serve as the President of the South Division of FB&T, reporting to the Chief Executive Officer of FB&T, and as the vice chairman of the board of directors of FB&T. The Wade employment agreement provides for an initial term of three years. Pursuant to the Wade employment agreement, if Mr. Wade continues to be employed by FB&T after the initial three-year term, he will do so as an at-will employee and not pursuant to the Wade employment agreement, unless otherwise agreed to by the parties to the agreement. The Wade employment agreement provides for a base salary of $300,000 per year, a one-time signing bonus of $100,000, an annual retention bonus of $50,000 for the first three years of employment, an annual cash incentive bonus targeted at 45% of his base salary, and annual grants of Heartland restricted stock units having a fair market value on the date of grant of up to 35% of his annual base salary. Mr. Wade will also be subject to certain ongoing confidentiality, noncompetition and nonsolicitation obligations. If Mr. Wade's employment is terminated by Heartland or FB&T without cause (as defined in the Wade employment agreement), subject to execution of a general release of claims, he will be entitled to receive (a) salary and benefits through though the date of termination and (b) his base salary for the remainder of the initial three-year term of the Wade employment agreement.

Ferrell Employment Agreement. Heartland, FB&T, AIM and AimBank have executed an employment agreement with Mr. Jeremy Ferrell that will become effective upon completion of the merger (the “Ferrell employment agreement”). The Ferrell employment agreement provides that Mr. Ferrell will serve as Chief Integration Officer of FB&T, reporting to the Chief Executive Officer of FB&T, and as an advisory member of the board of directors of FB&T. The Ferrell employment agreement provides for an initial term of three years. Except as otherwise agreed, if Mr. Ferrell continues to be employed by FB&T after the initial three-year term, he will do so as an at-will employee and not pursuant to the Ferrell employment agreement. The Ferrell

employment agreement provides for a base salary of $285,000 per year, a one-time signing bonus of $100,000, an annual retention bonus of $50,000 for the first three years of employment, an annual cash incentive bonus targeted at 45% of his base salary and annual grants of Heartland restricted stock units having a fair market value on the date of grant of up to 35% of his annual base salary. Mr. Ferrell will also be subject to certain ongoing confidentiality, noncompetition and nonsolicitation obligations. If Mr. Ferrell's employment is terminated by Heartland or FB&T without cause (as defined in the Ferrell employment agreement), subject to execution of a general release of claims, he will be entitled to received (a) salary and benefits through though the date of termination and (b) his base salary for the remainder of the initial three-year term of the Ferrell agreement.

Deferred Compensation Payments. In connection with the closing of the merger, AIM will terminate certain outstanding deferred compensation agreements, salary continuation agreements and additional compensation agreements and pay the amounts accelerated thereunder to the applicable beneficiaries of those agreements, which include certain executive officers of AIM, including Jeremy Ferrell, Scott L. Wade and Kenneth D. Willmon.

Retention Agreements. The merger agreement provides that AIM will use commercially reasonable efforts to cause certain senior executives of AimBank to execute retention agreements, providing for, among other things, (a) payments to be made to such senior executives if they remain in the employment of FB&T for the periods specified therein, and (b) the termination of any existing compensation agreements currently in effect with such senior executives.

Appointment of AimBank Directors to FB&T Board of Directors. The bank merger agreement provides that at or immediately following the effective time of the merger, at least four members of AimBank's board of directors will be appointed to FB&T's board of directors, one of whom will be Scott L. Wade, Chairman of the Board and Chief Executive Officer of AIM and AimBank.

Indemnification and Insurance of Directors and Officers. From and following the effective time, the current and former directors and officers of AIM will be entitled to indemnification from Heartland to the same extent and subject to the conditions set forth in the certificate of formation and bylaws of AIM or as required by law. Heartland has also agreed to maintain in effect for a period of six years following the effective time of the merger the directors' and officers' liability insurance policy currently maintained by AIM or to provide a policy with comparable or higher coverage, provided that, to obtain such insurance coverage, Heartland is not obligated to expend more than 200% of the annual cost currently expended by AIM for such insurance. Any indemnification provided to current and former officers and directors of AIM is only to the extent such indemnification is permitted by any applicable federal or state laws.

Employee Matters. Certain key employees of AimBank with important customer relationship responsibilities have entered into employment agreements with FB&T, Heartland, AimBank and AIM that will become effective upon completion of the merger (the “key employee employment agreements”). The key employee employment agreements supersede all existing compensation agreements among the key employees, AIM and AimBank. Under the key employee employment agreements, the key employees receive a base salary and signing and retention bonuses and are eligible to receive cash incentive bonuses. The key employee are subject to confidentiality, noncompetition and employee nonsolicitation agreements provided for in the key employee employment agreements.

Each person who is an employee of AIM or any of its subsidiaries as of the effective time of the merger will (a) become an employee of Heartland or FB&T, and (b) be eligible to participate in the health, vacation, and other non-equity based employee benefit plans of Heartland or its subsidiaries. With respect to any group health plan, Heartland will waive or cause to be waived any eligibility waiting periods or pre-existing condition limitations or similar limitations and credit each continuing employee for any co-payments or deductibles paid prior to the transfer to a Heartland group health plan in satisfying applicable deductible and annual out-of-pocket expense requirements under any Heartland such group health plan.

Continuing employees will receive prior service credit under Heartland's employee benefit plans for purposes of eligibility, vesting and level of benefits, provided that such recognition of service will not (a) operate to duplicate any benefits with respect to the same period of service or (b) apply if such service was not recognized under the corresponding AIM benefit plan.

Each employee of AIM or its subsidiaries whose employment is terminated without cause following the closing date of the merger will be offered severance benefits approximately equivalent to one week of base compensation for each full year of service to AIM (or its subsidiaries) with a minimum of two and a maximum of 12 weeks of severance pay, on terms and conditions to be established in the sole discretion of Heartland.

Heartland and AIM have agreed to use all commercially reasonable efforts to obtain all regulatory approvals required to complete the transactions contemplated by the merger agreement. Heartland is required to file an application with the FRB for approval to acquire AIM pursuant to the Bank Holding Act of 1956 (or obtain a waiver of such approval). FB&T must obtain approval from the FDIC to acquire AimBank under the Bank Merger Act and from the Texas Department of Banking (the “TDB”). FB&T and NMB&T also are required to obtain the approval of the FDIC, the TDB and the NMFID to transfer the assets and liabilities of AimBank's New Mexico branches to NMB&T. Heartland and AIM intend to complete the filing of applications (or waiver requests) with respect to these required regulatory approvals from the FRB, the FDIC, the TDB and the NFID shortly after the date of this proxy statement/prospectus.

A transaction approved pursuant to the Bank Holding Company Act of 1956 may not be completed until 30 days after approval is received. During which time, the Antitrust Division of the U.S. Department of Justice may challenge such transaction. The commencement of an antitrust action would stay the effectiveness of an approval unless a court specifically orders otherwise. With the consent of the Antitrust Division, the waiting period may be reduced to no less than 15 days.

Heartland and AIM are not aware of any material governmental approvals or actions that are required for completion of the merger other than those described above. It is presently contemplated that if any such additional government approvals or actions are required, those approvals or actions will be sought.

Heartland and AIM believe that neither the merger of AIM with and into Heartland nor the merger of AimBank with and into FB&T raises significant regulatory concerns and that they will be able to obtain all requisite regulatory approvals on a timely basis without the imposition of any condition that could reasonably be expected to have a material adverse effect on AIM, AimBank, FB&T or Heartland. However, there can be no assurance that all of the regulatory approvals described above will be obtained, and, if obtained, that the approvals will be received on a timely basis or that there will not be any litigation challenging such approvals. Likewise, no assurance can be provided that the Antitrust Division of the U.S. Department of Justice or any state attorney general will not attempt to challenge the merger on antitrust grounds. If such a challenge is made, the result of the challenge cannot be predicted.

Introduction. The following discussion describes the anticipated material U.S. federal income tax consequences to U.S. Holders (as defined below) that exchange their shares of AIM common stock for Heartland common stock and cash in the merger.

This discussion is based on the Code, administrative pronouncements, judicial decisions and Treasury Regulations, each as in effect as of the date of this proxy statement/prospectus. The legal authority on which this discussion is based is subject to change at any time, possibly with retroactive effect, and all of the federal tax consequences of the merger are subject to differing interpretations. No advance ruling has been or will be sought or obtained from the U.S. Internal Revenue Service (the “IRS”) regarding the U.S. federal income tax consequences of the merger. As a result, no assurance can be given that the IRS would not assert, or that a court would not sustain, a position contrary to any of the tax consequences set forth herein.

For purposes of this discussion, a “U.S. Holder” is a beneficial owner of AIM common stock that is for U.S. federal income tax purposes:

If a partnership (including for this purpose any entity or arrangement treated as a partnership for U.S. federal income tax purposes) holds shares of AIM common stock, the tax treatment of a partner will generally depend on the status of the partner and the activities of the partnership. Any entity or arrangement treated as a partnership for U.S. federal income tax purposes that holds shares of AIM common stock, and any owners of such an entity or arrangement, should consult their own tax advisors regarding the tax consequences of the merger in light of their specific circumstances.

This discussion does not address any tax consequences of the merger to persons who are not U.S. Holders. This discussion assumes that U.S. Holders hold their AIM common stock as capital assets within the meaning of Section 1221 of the Code (generally, as property held for investment). This discussion does not address any tax consequences arising under U.S. federal tax laws other than U.S. federal income tax laws, nor does it address the laws of any state, local, foreign or other taxing jurisdiction. In addition, this discussion does not address all aspects of U.S. federal income taxation that may apply to U.S. Holders in light of their particular circumstances, or U.S. Holders that are subject to special rules under the Code, such as holders of AIM common stock that are pass-through entities or trusts, persons who acquired shares of AIM common stock as a result of the exercise of employee stock options or otherwise as compensation or through a tax-qualified retirement plan, persons subject to the U.S. federal alternative minimum tax or net investment income tax, persons required to accelerate the recognition of any item of gross income in connection with the merger as a result of recognition of such income on an applicable financial statement, tax-exempt organizations, banks and other financial institutions, insurance companies, regulated investment companies, real estate investment trusts, broker-dealers, traders in securities that have elected to apply a mark-to-market method of accounting, persons having a “functional currency” other than the U.S. dollar, U.S. expatriates, persons who acquired their AIM common stock through the conversion of a debt instrument and persons holding their AIM common stock as part of a straddle, hedging, constructive sale, conversion transaction or other integrated investment.

U.S. Holders should consult with their own tax advisors regarding the specific tax consequences of the merger in light of their particular circumstances, including the tax consequences under state, local, foreign and other tax laws and the possible effects of changes in the U.S. federal or other tax laws.

Tax Classification of the Merger. The merger is intended to qualify as a reorganization under Section 368(a) of the Code. The obligations of AIM to complete the merger are subject to (among other conditions, as described in this proxy statement/prospectus and the merger agreement) the receipt of the opinion of Fenimore, Kay, Harrison & Ford, LLP (“FKHF”), counsel to AIM, that the merger will qualify as a “reorganization” under Section 368(a) of the Code. AIM does not currently intend to waive this opinion condition to its obligations to complete the merger.

In rendering its opinion, FKHF will rely on certain assumptions, including assumptions regarding the absence of changes in existing facts and law and the completion of the merger in the manner contemplated by the merger agreement, and on representations and covenants made by AIM and Heartland, including those contained in representation letters of officers of AIM and Heartland. If any of these assumptions or representations is incomplete or inaccurate in any way, or any of these covenants is not satisfied, the tax consequences of the merger could be materially different from what is described herein. An opinion of counsel represents counsel's best legal judgment and is not binding on the IRS or any court, nor does it preclude the IRS from adopting a contrary position.

Exchange of AIM Common Stock for Heartland Common Stock. Based on and subject to the foregoing, provided that, in accordance with the opinion described above, the merger qualifies as a “reorganization” within the meaning of Section 368(a) of the Code, the U.S. federal income tax consequences of the merger to U.S. Holders are as follows:

If a U.S. Holder exchanges more than one “block” of shares of AIM common stock (that is, groups of shares that the U.S. Holder acquired at different times or at different prices), the U.S. Holder must calculate gain, adjusted tax basis and holding period separately as to each block of shares. Any such U.S. Holder should consult with his, her or its own tax advisors regarding the manner in which shares of Heartland common stock and cash received in the merger should be allocated among different blocks of shares of AIM common stock for purposes of determining recognized gain and the tax bases and holding periods of the particular shares of Heartland common stock received in the merger.

Cash in lieu of Fractional Shares. To the extent that a U.S. Holder receives cash in lieu of a fractional share of Heartland common stock, the U.S. Holder will be deemed to have received that fractional share in the merger and then to have received the cash in redemption of that fractional share by Heartland. The U.S. Holder generally will recognize gain or loss equal to the difference between the cash received and the portion of the U.S. Holder's adjusted tax basis in the shares of AIM common stock surrendered allocable to that fractional share. This gain or loss generally will be long-term capital gain or loss if the holding period for those shares of AIM common stock is more than one year as of the date of the merger, unless the receipt of cash has the effect of a distribution of a dividend under the provisions of the Code (as discussed above). The deductibility of capital losses is subject to limitations.

Backup Withholding. Backup withholding at the applicable rate may, under certain circumstances, apply unless a U.S. Holder (a) is a corporation or is within certain other exempt categories and, when required, demonstrates this fact, or (b) provides a correct taxpayer identification number, certifies as to no loss of exemption from backup withholding and otherwise complies with applicable requirements of the backup withholding rules. A U.S. Holder who does not provide his, her or its correct taxpayer identification number may be subject to penalties imposed by the IRS. Any amounts withheld under the backup withholding rules may be allowed as a refund or a credit against the U.S. Holder's U.S. federal income tax liability, provided the U.S. Holder furnishes certain required information to the IRS.

Reporting Requirements. A U.S. Holder will be required to retain records pertaining to the merger and will be required to file with such U.S. Holder's U.S. federal income tax return for the year in which the merger takes place a statement setting forth certain facts relating to the merger. In addition, each U.S. Holder who is a “significant holder” that receives Heartland common stock in the merger will be required to file a statement with his, her or its U.S. federal income tax return setting forth his, her or its adjusted tax basis in the AIM common stock surrendered and the fair market value of the Heartland common stock received in the merger. A “significant holder” is a holder of AIM common stock who, immediately before the merger, owned at least one percent (by vote or value) of the outstanding shares of AIM common stock or owned AIM securities with an adjusted tax basis of $1,000,000 or more.

TAX MATTERS REGARDING THE MERGER ARE COMPLICATED, AND THE TAX CONSEQUENCES OF THE MERGER TO ANY PARTICULAR AIM SHAREHOLDER WILL DEPEND ON THAT SHAREHOLDER'S PARTICULAR SITUATION. AIM SHAREHOLDERS SHOULD CONSULT THEIR OWN TAX ADVISORS REGARDING THE SPECIFIC TAX CONSEQUENCES OF THE MERGER, INCLUDING TAX RETURN REPORTING REQUIREMENTS, THE APPLICABILITY OF FEDERAL, STATE, LOCAL AND FOREIGN TAX LAWS AND THE EFFECT OF ANY PROPOSED CHANGE IN THE TAX LAWS TO THEM.

The merger of AIM into Heartland will be accounted for under the acquisition method of accounting by Heartland, as that term is used under GAAP, for accounting and financial reporting purposes. As a result, the historical financial statements of Heartland will continue to be the historical financial statements of Heartland following the completion of the merger. The assets (including identifiable intangible assets) and liabilities (including executory contracts and other commitments) of AIM as of the effective time of the merger will be recorded at their respective fair values and added to the assets and liabilities of Heartland. Any excess of the aggregate merger consideration over the net fair values of AIM assets and liabilities is recorded as goodwill (i.e., excess purchase price). Financial statements of Heartland issued after the merger will reflect such fair values and will not be restated retroactively to reflect the historical financial position or results of operations of AIM. The results of operations of AIM will be included in the results of operations of Heartland beginning on the effective date of the merger.

The composition of Heartland's board of directors and its senior management will not be changed as a result of the merger. Information about the current Heartland directors and executive officers can be found in Heartland's proxy statement dated April 6, 2020 for its 2020 Annual Meeting of Shareholders. See the section of this proxy statement/prospectus titled “Where You Can Find More Information.”

General. If you hold one or more shares of AIM common stock, you have the right to dissent from the merger and have the appraised fair value of your shares of AIM common stock paid to you in cash. The ultimate amount that a dissenting shareholder receives in an appraisal proceeding may be less than, equal to or more than the amount he or she would have received under the merger agreement. If you are contemplating exercising your right to dissent, we urge you to read carefully the provisions of Chapter 10, Subchapter H of the TBOC, which are attached as Appendix B to this proxy statement/prospectus, and consult with your legal counsel before electing or attempting to exercise these rights. The following summary describes the steps you must take if you want to exercise your right to dissent. This summary, however, is not a complete statement of all applicable requirements and is qualified in its entirety by reference to Chapter 10, Subchapter H of the TBOC. You should read this summary and the full text of the law carefully.

How to Exercise and Perfect Your Right to Dissent. To be eligible to exercise your right to dissent to the merger: