We are happy to advise you that the board of directors of AIM Bancshares, Inc. (“AIM”) has unanimously approved a transaction in which Heartland Financial USA, Inc. (“Heartland”), will effectively acquire AIM and AimBank, a Texas state-chartered bank and wholly owned subsidiary of AIM (“AimBank”), in a two-step transaction. In the first step, AIM will merge with and into AimBank (the “AIM/AimBank merger”) in accordance with an Agreement and Plan of Merger dated as of September 22, 2020 (the “AIM/AimBank merger agreement”). In the second step, which will occur immediately following the consummation of the AIM/AimBank merger, AimBank will merge with and into First Bank & Trust (“FB&T”), a Texas-state chartered bank and wholly owned subsidiary of Heartland (the “FB&T/AimBank merger”, which, together with the AIM/AimBank merger, is sometimes collectively referred to herein as the “merger”) in accordance with an Amended and Restated Agreement and Plan of Merger dated as of October 19, 2020 (the “amended and restated merger agreement”, which, together with the AIM/AimBank merger agreement, is sometimes collectively referred to herein as the “merger agreement”). Before we can complete the AIM/AimBank 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 AIM/AimBank merger agreement. The AIM board of directors unanimously recommends that you vote “FOR” approval of the AIM/AimBank merger agreement.

In the AIM/AimBank merger, AIM will merge with and into AimBank, and holders of shares of AIM common stock will receive one share of AimBank common stock for each share of AIM common stock owned by such holders immediately prior to the effective time of the AIM/AimBank merger. As of the date of this proxy statement/prospectus, AIM shareholders owned 24,553.98 shares of AIM common stock, which will be converted into an equal number of shares of AimBank common stock in the AIM/AimBank merger. The consummation of the FB&T/AimBank merger will occur immediately following the consummation of the AIM/AimBank merger (such date and time, the “closing date” and the “effective time”, respectively), and you, as the holder of shares of AimBank common stock after the AIM/AimBank merger, will receive in exchange for each share of AimBank common stock that you own as of the effective time of the FB&T/AimBank merger, 207.0 shares of Heartland common stock (the “stock exchange ratio”) and $685.00 of cash (the “cash exchange ratio”, and together with the stock exchange ratio, the “merger consideration”), each ratio subject to adjustment as further described in this proxy statement/prospectus, plus cash in lieu of any fractional shares. The merger consideration payable as a result of the FB&T/AimBank merger may be reduced by a holdback amount, if any, to be determined on the closing date based on the status of a certain litigation proceeding as of three business days prior to the closing date and the amount of net income earned by AIM from December 1, 2020 to the closing date, if any, as described under the section titled “The Amended and Restated Merger Agreement – The FB&T/AimBank Merger – Aggregate Holdback Amount”. As of the date of the amended and restated merger agreement, the aggregate holdback amount was $5.0 million (or $203.63 per share of AimBank common stock), which amount is subject to adjustment as described herein.

In the AIM/AimBank merger, options to acquire shares of AIM common stock outstanding and unexercised on the closing date of the AIM/AimBank merger (the “AIM stock options”) will be converted into options to purchase AimBank common stock (the “AimBank stock options”) on exactly the same terms and conditions as the AIM stock options (including the option exercise price), except that AimBank common stock rather than AIM common stock, will be issued upon the exercise of the AimBank stock options. In the FB&T/AimBank merger, holders of AimBank stock options will be entitled to receive a cash payment equal to the product of (a) the number of shares of AimBank common stock subject to such AimBank stock option, and (b) the excess of (i) an amount determined by (A) multiplying 207.0 (subject to adjustment) 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), over (ii) the exercise price per share of such AimBank 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 AimBank stock option is a negative number, the holder of the AimBank stock option will not be entitled to any such cash payment. However, the option consideration will not be reduced by the aggregate holdback amount, if any, that may be applied to the cash component of the merger consideration. As of September 30, 2020, 1,660 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, it 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 Amended and Restated Merger Agreement—Termination” in this proxy statement/prospectus, AIM may exercise a “walk-away” right to terminate the amended and restated 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 Amended and Restated Merger Agreement—Termination” in this proxy statement/prospectus, Heartland may exercise a “walk-away” right to terminate the amended and restated merger agreement unless AIM accepts, at its option, either a decrease in the stock exchange ratio or the cash exchange ratio to avoid Heartland's termination of the amended and restated merger agreement.

The cash exchange ratio is fixed, but may be adjusted in two instances. First, in the event AIM's adjusted tangible common equity (as defined in this proxy statement/prospectus in the section titled “The Amended and Restated Merger Agreement—The FB&T/AimBank 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 $145.0 million, 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 $145.0 million.

Second, if AIM's adjusted tangible common equity as of the determination date is greater than $146.0 million, the cash component of the merger consideration will be increased by an amount by which the adjusted tangible common equity is above $146.0 million.

Based on the closing price of a share of Heartland common stock as of October 16, 2020 of $33.30, the aggregate merger consideration was valued at approximately $218.1 million with (a) AimBank shareholders (as former AIM shareholders) receiving aggregate consideration of approximately $212.0 million, or $8,635.56 for each share of AimBank common stock and (b) holders of AimBank stock options (as former holders of AIM stock options) receiving aggregate option consideration of approximately $6.1 million. These valuations are based on the assumption that the cash exchange ratio is adjusted based on AIM's adjusted tangible common equity of approximately $172.0 million as of September 30, 2020, and before adjusting for an aggregate holdback amount of $5.0 million. As of September 30, 2020, the book value per share of AIM common stock was $7,736.11 and the tangible book value per share of AIM common stock was $6,755.28. 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 closing date of the merger, the adjusted tangible common equity of AIM may increase or decrease, and the aggregate holdback amount may increase or decrease, the value and amount, respectively, of the actual consideration you will receive may be different from the amounts described above.

For illustration purposes only, the following table presents the value of the merger consideration for each share of AimBank common stock, based upon various levels of AIM’s adjusted tangible common equity. As of September 30, 2020, AIM’s adjusted tangible common equity was approximately $172.0 million

To complete the AIM/AimBank merger, certain regulatory approvals must be received and the holders of at least two-thirds of the issued and outstanding shares of AIM common stock entitled to vote must approve the AIM/AimBank merger proposal (as defined below). The FB&T/AimBank merger will not require a separate vote of the holders of AIM common stock.

At its 2020 annual meeting of shareholders (the “annual meeting”), AIM will be seeking the shareholder approval necessary to approve the AIM/AimBank merger proposal. 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 AIM/AimBank merger proposal.

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 both the AIM/AimBank merger and the FB&T/AimBank merger and includes a copy of the AIM/AimBank merger agreement as Appendix A and a copy of the amended and restated merger agreement as Appendix B.

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. will hold an annual meeting of its shareholders at              , at      local time on     , 2020, to consider and vote upon the following matters:

The accompanying proxy statement/prospectus contains a detailed discussion of the AIM/AimBank merger, the FB&T/AimBank merger and certain transactions related thereto, and includes a copy of the AIM/AimBank merger agreement as Appendix A and a copy of the amended and restated merger agreement as Appendix B.

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” the AIM/AimBank merger proposal. In addition, the AIM board of directors unanimously recommends that you vote “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 AIM/AimBank merger proposal 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 C to the accompanying 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 accompanying 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.

The following section provides answers to some commonly asked questions about (i) the merger of AIM Bancshares, Inc. (“AIM”) with and into AimBank, a wholly owned subsidiary of AIM and Texas-state chartered bank (the “AIM/AimBank merger”), (ii) the merger of AimBank with and into First Bank & Trust (“FB&T”), a wholly owned subsidiary of Heartland Financial USA, Inc. (“Heartland”) and a Texas-state chartered bank (the “FB&T/AimBank merger”, which, together with the AIM/AimBank merger, is sometimes collectively referred to herein as the “merger”), and (iii) the annual meeting of AIM shareholders (the “annual meeting”) to be held to approve the AIM/AimBank merger and elect the four AIM director nominees named in this proxy statement/prospectus. This section may not include all the information that may be important to you. You should read this entire proxy statement/prospectus carefully, including the Appendices, and any additional documents incorporated by reference herein to fully understand the AIM/AimBank merger agreement (as defined below), the amended and restated merger agreement (as defined below), and the transactions contemplated thereby, including the AIM/AimBank merger, the FB&T/AimBank merger, the proposals to be considered at the annual meeting, the voting procedures for the annual meeting, the issuance of Heartland common stock in connection with the merger and the risks of owning Heartland common stock.

COVID-19. The spread of COVID-19 has created a global public health crisis 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, and 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 Board will maintain a low interest rate environment for the foreseeable future. Although some previously-closed businesses have resumed operations, the COVID-19 pandemic continues to impact Heartland’s business in material ways.

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, cash flows, 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 which are highly uncertain, including the scope, severity and duration of the COVID-19 pandemic, the actions taken to contain the COVID-19

pandemic or mitigate its impact, and the direct and indirect economic effects of the COVID-19 pandemic and containment measures, among other future developments.

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 and $26.8 million of provision for credit losses in the first quarter of 2020 and the second quarter of 2020, respectively, primarily due to a deteriorating economic outlook resulting in an increase in expected credit losses.

These factors may remain prevalent for a significant period of time and may continue to adversely affect Heartland's business, results of operations, financial conditions, liquidity and prospects even after the COVID-19 pandemic has subsided.

In addition, the COVID-19 pandemic has significantly affected the financial markets and has resulted in a number of Federal Reserve actions. Market interest rates have declined significantly. In March 2020, the Federal Reserve reduced the target federal funds rate, and in September 2020, it announced that the low rate would be maintained until (i) labor market conditions have reached levels consistent with the Committee’s assessments of maximum employment and (ii) inflation has risen to 2 percent and is expected to moderately exceed 2 percent for some time. Heartland expects that these reductions in interest rates, especially if prolonged, could adversely affect Heartland’s net interest income and margins and profitability. The Federal Reserve also (i) announced a $700 billion quantitative easing program in response to the expected economic downturn caused by COVID-19 and (ii) launched the Main Street Lending Program, which will offer deferred interest on four-year loans to small and mid-sized businesses. The full impact of the COVID-19 pandemic on Heartland’s business activities as a result of new government and regulatory policies, programs and guidelines, as well as market reactions to such activities, remains uncertain.

Heartland's subsidiary banks 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 amount of time between the passage of the CARES Act and the opening of the PPP, there was some ambiguity in the laws, rules and guidance regarding the operation of the PPP, which has exposed Heartland 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. The PPP was modified on June 5, 2020, with the adoption of the Paycheck Protection Program Flexibility Act (the “PPFA”). The PPFA increased the amount of time that borrowers have to use PPP loan proceeds and apply for loan forgiveness and made other changes to make the program more favorable to borrowers. Notwithstanding the foregoing, Heartland's subsidiary banks 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.

Heartland's subsidiary banks 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.

In addition, while the COVID-19 pandemic had a material impact on the provision for credit losses, Heartland is unable to fully predict the impact that the COVID-19 pandemic will have on the credit quality of

the loan portfolios of Heartland’s subsidiary banks, and any acquired banks, Heartland financial position or results of operations due to numerous uncertainties. Heartland will continue to assess the potential impacts on the credit quality of the loan portfolios of Heartland’s subsidiary banks and any acquired banks, its financial positions and results of operations.

The extent to which the COVID-19 pandemic impacts Heartland's business, 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 COVID-19 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 its 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 June 30, 2020.

At the effective time of the AIM/AimBank merger, each share of AIM common stock will be converted into the right to receive one share of AimBank common stock. Immediately thereafter, at the effective time of the FB&T/AimBank merger, each share of AimBank common stock will be converted into the right to receive the stock exchange ratio (207.0 shares of Heartland common stock) and the cash exchange ratio ($685.00 of cash), each ratio subject to adjustment as further described in this proxy statement/prospectus. The stock exchange ratio will not increase or decrease solely 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 amended and restated 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 the cash exchange ratio to void the “walk-away” right as described in the section of this proxy statement/prospectus titled “The Amended and Restated 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 Amended and Restated Merger Agreement—Termination” in this proxy statement/prospectus, Heartland may exercise a “walk-away” right to terminate the amended and restated merger agreement unless AIM agrees to a decrease, at its option, in either the stock exchange ratio or the cash exchange ratio to avoid the termination of the amended and restated merger agreement by Heartland. The market value of Heartland common stock has declined significantly since Heartland and AIM entered into the original 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 COVID-19 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 $145.0 million. Although it appears unlikely AIM’s adjusted tangible common equity will fall below $145.0 million, reductions in adjusted tangible common equity could result from higher loan loss provisions, ordinary business conditions that impact the net interest and noninterest income of AIM, the financial effects of the COVID-19 pandemic or more general market and economic conditions that impact AIM operations.

As of September 30, 2020, AIM’s adjusted tangible common equity was approximately $172.0 million.

The aggregate amount of cash consideration that AIM shareholders receive in the merger may be reduced by an amount equal to the aggregate holdback amount. The aggregate holdback amount will be equal to the sum of (a) $5.0 million, plus (b) the net income earned by AIM from December 1, 2020 to the closing date, if any, plus (c) the amount by which the damages sought in the Reagor-Dykes litigation as of three business days prior to the closing date exceed the amount of damages sought in the Reagor-Dykes litigation as of the date of the amended and restated merger agreement. These amounts are unknown at this time, and AIM shareholders may receive considerably less cash consideration then they would otherwise be paid in the merger because of the holdback provision in the amended and restated merger agreement.

The spread of COVID-19 throughout the United States, and the measures taken by national, regional and local governmental authorities attempting to contain the spread and impact of COVID-19, including the declaration of a federal National Emergency; multiple cities’ and states’ declarations of states of emergency; school and business closings; limitations on social or public gatherings and other social distancing measures, such as working remotely; travel restrictions, quarantines and shelter-in-place orders. Such measures have significantly contributed to rising unemployment and negatively impacted consumer and business spending, borrowing needs, and savings habits. Although some of the measures have been lifted, it remains possible that these measures could be reinstated. In addition, the COVID-19 pandemic is still 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 COVID-19 pandemic on the businesses of Heartland and AIM, and there is no guarantee that efforts by Heartland and AIM to address the adverse impacts of the COVID-19 pandemic 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 regarding the nature 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 pandemic, 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 pandemic, 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.

The transactions contemplated by the Aim/AimBank merger agreement and the FB&T/AimBank merger have been approved by the FDIC. However, before the FB&T/AimBank merger may be completed, approvals must be obtained from state bank regulators, including the TDB. The TDB will consider, among other factors, 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 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. Although all regulatory applications have

been filed, these applications were filed prior to the execution of the amended and restated merger agreement and will be amended to reflect the changes made in the amended and restated merger agreement. Regulatory approvals of the AIM/AimBank merger and the FB&T/AimBank merger will be subject to regulatory review of the amended applications. There can be no assurance as to whether approvals from the TDB will be received, the timing of such approval, 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 COVID-19 pandemic 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—Interests of AIM’s Directors and Executive Officers in the Merger.” These interests and arrangements may cause the directors and executive officers to view the AIM/AimBank 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 unanimously approve the merger agreement and unanimously recommend that AIM shareholders approve the AIM/AimBank merger proposal.

Consummation of the AIM/AimBank merger and the FB&T/AimBank merger are subject to customary conditions to closing in addition to the receipt of required bank regulatory approvals and approval of the AIM/AimBank merger proposal by the requisite vote of the AIM shareholders. If any condition to the AIM/AimBank merger is not satisfied or waived, neither the AIM/AimBank merger nor the FB&T/AimBank will be completed. In addition, Heartland and AIM may terminate the amended and restated merger agreement under certain circumstances even if the AIM/AimBank merger agreement is approved by the AIM shareholders, including the circumstance that the merger has not been completed on or before February 28, 2021. 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 amended and restated 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 AIM/AimBank merger and the FB&T/AimBank merger, see the sections titled “The AIM/AimBank Merger Agreement—Conditions to Completion of the AIM/AimBank Merger” and “The Amended and Restated Merger Agreement—Conditions to Completion of the FB&T/AimBank 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 and AimBank are 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 amended and restated merger agreement is terminated in specified circumstances, including the circumstance in which AIM terminates the amended and restated merger agreement to enter into a superior proposal with another entity. These provisions could discourage other companies from trying to acquire AimBank even though those other companies might be willing to offer greater value to AIM's shareholders than Heartland has offered in the amended and restated merger agreement. See the sections titled “The Amended and Restated Merger Agreement—Termination” and “The Amended and Restated 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 transaction, has delivered to the board of directors of AIM its opinion dated as of October 8, 2020. The Magstar opinion states that as of such date, and based upon and subject to the factors and assumptions set forth therein, the merger 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 COVID-19 pandemic, 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 COVID-19 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 pandemic.

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 COVID-19 pandemic; (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 COVID-19 pandemic, 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 COVID-19, 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:

The COVID-19 pandemic is adversely affecting Heartland and AIM and their customers, counterparties, employees and third-party service providers. The COVID-19 pandemic’s severity, its duration and the extent of its impact on Heartland’s and AIM’s business, financial condition, results of operations, liquidity and prospects remain uncertain. The deterioration in general business and economic conditions and turbulence in domestic and global financial markets caused by the COVID-19 pandemic have negatively affected Heartland’s and AIM’s net income, total equity and book value per common share, and continued economic deterioration could adversely affect the value of their assets and liabilities, reduce the availability of funding to Heartland and AIM, lead to a tightening of credit and increase stock price volatility in the case of Heartland. Some economists and investment banks believe that a recession or depression may result from the continued spread of COVID-19 and the economic consequences.

These risks and uncertainties should be considered in evaluating forward-looking statements, and undue reliance should not be placed on these statements. Heartland and AIM do not undertake, and specifically disclaim any obligation, to publicly release the result of any revisions which may be made to any forward-looking statements to reflect events or circumstances after the date of such statements or to reflect the occurrence of anticipated or unanticipated events.

There can be no assurance that other factors not currently anticipated by Heartland and AIM will not materially and adversely affect Heartland’s and AIM’s business, financial condition and results of operations. In addition, many of these risks and uncertainties are currently amplified by and may continue to be amplified by or may, in the future, be amplified by, the recent outbreak of the COVID-19 pandemic and the impact of varying governmental responses that affect Heartland’s and AIM’s customers and the economies where they operate. You are cautioned not to place undue reliance on any forward-looking statements made by Heartland, AIM, or on their behalf. Please take into account that forward-looking statements speak only as of the date of this proxy statement/prospectus or, in the case of documents incorporated by reference herein or therein, the date of any such document. Except as required by applicable law, neither Heartland nor AIM undertakes any obligation to publicly correct or update any forward-looking statement. 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 has unanimously approved the merger agreement and unanimously recommends that holders of AIM common stock vote “FOR” the AIM/AimBank merger proposal. In addition, the AIM board of directors unanimously recommends that you vote “FOR” the election of the AIM director nominees set forth above (and described below under the section titled “The Annual Meeting—Election of AIM Directors.”) and “FOR” the adjournment of the annual meeting for the purpose described above.

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 on the AIM/AimBank merger proposal, you must follow such voting instructions. The KSOP plan committee will direct the KSOP trustee with respect to voting on all other matters to be considered at the annual meeting.

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 AIM/AimBank 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 AIM/AimBank merger proposal requires the affirmative vote of the holders of at least two-thirds of the issued and outstanding shares of AIM common stock entitled to vote on such proposal. 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 AIM/AimBank merger proposal, it will have the effect of a vote “AGAINST” the AIM/AimBank 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.

The affirmative vote of the holders of a majority of the shares of AIM common stock entitled to vote and represented in person or by proxy at the annual meeting is required to approve the adjournment proposal. If you are represented in person or by proxy at the annual meeting but abstain or fail to vote on the adjournment proposal, 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 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 27.9% 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 AIM/AimBank merger proposal, which is required to be approved by the holders of two-thirds of the issued and outstanding shares of AIM common stock entitled to vote on such proposal. Abstentions also will have the same effect as a vote “AGAINST” the AIM/AimBank merger proposal. Accordingly, the AIM board of directors urges holders of AIM common stock to vote on the AIM/AimBank merger proposal prior to or at the annual meeting.

Voting Agreement. Pursuant to an amended and restated shareholder voting agreement, certain holders of shares of AIM common stock have agreed to vote their shares in favor of the AIM/AimBank merger proposal. Under the terms of the amended and restated 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 AIM/AimBank merger proposal. The holders of AIM common stock who have agreed to vote for the AIM/AimBank merger proposal have the right to vote, or direct the voting of, 27.9% of the outstanding shares of AIM common stock as of the record date. In the event the amended and restated merger agreement is terminated, the amended and restated 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 AIM/AimBank 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 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 AIM/AimBank 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 AIM/AimBank 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 AIM/AimBank 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 AIM/AimBank 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 AIM/AimBank 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 AIM/AimBank 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 A. Duff; Jeremy C. 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 AIM/AimBank 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 AIM/AimBank 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 AIM/AimBank merger agreement provides that AIM will be merged with and into AimBank and AIM shareholders will receive one share of AimBank common stock for each share of AIM common stock owned by such holders immediately prior to the effective time of the AIM/AimBank merger. The amended and restated merger agreement provides that, immediately following the consummation of the AIM/AimBank merger, the FB&T/AimBank merger will occur, and AimBank will be merged with and into FB&T, and the holders of AimBank common stock issued and outstanding immediately prior to the effective time of the FB&T/AimBank merger will be converted into the right to receive the stock exchange ratio (207.0 shares of Heartland common stock) and the cash exchange ratio ($685.00 in cash), each ratio subject to adjustment as further described in this proxy statement/prospectus, plus cash in lieu of any fractional shares.

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 in which 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 the 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 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 and bank 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 acquisition 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 of the original merger agreement to AIM.

Heartland’s counsel sent an initial draft of the original merger agreement to AIM’s counsel on December 20, 2019, and Heartland and AIM negotiated the terms of the original merger agreement until it was finalized and executed in early February 2020.

On January 28, 2020, Hillworth and Fenimore 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 Magstar to discuss the original 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 original merger agreement and the ancillary documents thereto, including the provisions of the original merger agreement that permitted the AIM board to terminate the 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 of AIM into Heartland. The AIM board of directors addressed a series of questions to the representatives of Magstar 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 with AIM, which consisted of 207.0 shares of Heartland common stock and $685.00 in cash for each outstanding share of AIM common stock, 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 original 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.

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

On February 11, 2020, the trustees of the KSOP received an opinion from an independent valuation firm stating that (i) the consideration to be received by the KSOP pursuant to the original 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 the Employee Retirement Income Security Act of 1974) of such shares, and (ii) the terms and conditions of the original merger agreement, taken as a whole, were 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 of AIM into Heartland and the original 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 original merger agreement and strategic and financial considerations relating to the merger of AIM into Heartland. Heartland’s financial advisor, Stephens Inc. discussed financial aspects of the proposed transaction, and Stephens, Inc. 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, Inc. as set forth in such opinion, the merger consideration in the merger of AIM into Heartland was fair to Heartland from a financial point of view. Heartland's board of directors asked a number of questions of management and Stephens, Inc. regarding the terms and conditions of the original merger agreement and the strategic and economic aspects of the acquisition of AIM and engaged in a full discussion regarding the proposed transaction. Following this discussion, Heartland's board of directors unanimously voted to approve the original merger agreement and the transactions contemplated by the original merger agreement, including the merger of AIM into Heartland, and authorized Heartland's management to execute the original merger agreement.

On February 11, 2020, AIM and Heartland executed the original 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.

In the weeks following the announcement of the original merger agreement, the COVID-19 pandemic began adversely affecting U.S. financial markets and economic conditions and increasing stock market volatility. In March 2020, the World Health Organization declared the outbreak a global pandemic and President Donald J. Trump declared a national emergency to reduce the spread of COVID-19 and to provide for emergency funding to state and local governments for this purpose. During March and April 2020, federal, state and local authorities implemented numerous measures intended to contain the spread of COVID-19, such as travel bans and restrictions, quarantines, shelter in place orders and limitations on business activity, including closures.

On March 17, 2020, Heartland held a special board meeting. At this meeting, the board discussed the impact of the COVID-19 pandemic and stock market volatility on the proposed transaction between AIM and Heartland. Management informed the board that the transaction was expected to close in July 2020.

During March and April 2020, management of both AIM and Heartland were engaged in regular communication regarding the pending merger of AIM into Heartland and the effects of COVID-19 and the government efforts to contain its spread on both companies.

On May 18, 2020, Heartland filed a registration statement on Form S-4 with the SEC with respect to the shares of Heartland common stock to be issued pursuant to the original merger agreement. On May 26, 2020, the SEC notified Heartland that the SEC would not review the registration statement.

On May 22, 2020, Heartland filed a request with the Federal Reserve Board for a waiver of the application and prior approval requirements of Section 3 of the Bank Holding Company Act with respect to the proposed merger of AIM into Heartland. At that time, Heartland and FB&T also filed an Interagency Bank Merger Act Application with the FDIC seeking approval for the merger of AimBank into FB&T. In addition, Heartland and FB&T also filed an application with the TDB relating to the merger of AimBank into FB&T.

On May 28, 2020, representatives of Hillworth discussed with AIM’s management the impact of the COVID-19 pandemic on AIM. Also, financial forecasts were reviewed, especially in light of the lower interest rate environment. As a result of the drop in interest rates, AIM’s securities portfolio had a significant unrealized

gain in value. AIM and Hillworth also discussed the performance of AIM as well as the results of the recent PPP loan program under the CARES Act. AIM’s management requested Hillworth to provide an analysis of the current financial markets, and the effect of financial market conditions on the pending merger between AIM and Heartland.

On June 5, 2020, representatives of Hillworth discussed its analysis of the financial markets with AIM’s management. AIM directed Hillworth to contact Heartland to discuss the significant unrealized gain in AIM’s securities portfolio and certain AIM employee matters.

Between June 14, 2020, and June 18, 2020, Hillworth and Heartland held several telephone conferences to discuss AIM’s securities portfolio, the employee issues and an updated timetable for the transaction.

From June 25, 2020 to July 10, 2020, the Federal Reserve Board staff held discussions with Heartland representatives during which the staff raised concerns regarding the proposed transaction as it was structured in the original merger agreement. Heartland and the Federal Reserve Board discussed several options to address the Federal Reserve Board’s concerns, including a restructuring of the proposed transaction so that approval by the Federal Reserve Board would not be required. The proposed restructuring was also discussed with the FDIC and the TBD.

On July 13, 2020, Heartland further discussed the Federal Reserve Board’s concerns regarding the transaction and, with the prior approval of AIM, agreed to restructure the transaction in a manner consistent with the terms of the amended and restated merger agreement to eliminate the merger of AIM into Heartland. The Federal Reserve Board agreed that this restructuring of the transaction would eliminate the need for approval of the transaction by the Federal Reserve Board (or a waiver of the requirement that the Federal Reserve Board approve the transaction). On July 14, 2020, Heartland withdrew the waiver request made to the Federal Reserve Board.

On June 30, 2020, AIM’s management and board of directors discussed the acquisition of AIM with representatives from Hillworth. Hillworth provided an analysis of the current markets for regional banks and the broader mergers and acquisitions market and economic conditions in the United States. Hillworth also provided an update on the volatility of the trading price of Heartland common stock and its effect on the merger consideration provided for in the original merger agreement.

On July 3, 2020, AIM received a confidential settlement communication asserting claims against AimBank relating to the bankruptcy of the Reagor-Dykes automotive dealership, a former customer of AimBank. AIM promptly notified Heartland of the settlement communication.

During the month of July 2020, AIM and Hillworth, with the advice of legal counsel, discussed the claims against AimBank and explored various options for addressing these claims in light of the pending transaction with Heartland. AIM also had discussions with Heartland regarding the potential impact of the claims on the pending transaction if litigation was in fact initiated. In addition, discussions between AIM and Heartland continued regarding AIM’s securities portfolio, the impact of the COVID-19 pandemic on the businesses and operations of Heartland and AIM, U.S. economic conditions and volatility in the U.S. financial markets.

On July 16, 2020, AIM provided Heartland with a term sheet summarizing proposed revisions to the original merger agreement to reflect the restructuring of the transaction and to address certain other matters, including adjustments to the cash component of the merger consideration due to the delays in the closing of the transaction. Specifically, the term sheet provided that the threshold amount of AIM’s adjusted tangible common equity for determining an increase in the cash component of the merger consideration would be reduced to $146.0 million and the elimination of the cap on the increase in cash consideration, which was limited to $5.0 million under the original merger agreement. The term sheet also provided that any unrealized gains in AIM’s securities portfolio would adjust AIM’s adjusted tangible common equity upward by the amount of such unrealized gains. In addition, AIM proposed that certain retention payments (which totaled approximately $1.1 million) to be made to certain AimBank employees would be excluded from AIM’s transaction expenses when calculating the cash consideration to be paid pursuant to the amended and restated merger agreement. Finally, the term sheet provided that the cap on AIM’s transaction expenses (which had the potential to reduce the cash component of the merger consideration paid to AIM shareholders) would be increased from $8.5 million

to $8.8 million. In connection with its delivery of the term sheet, AIM requested that Heartland make a proposal regarding the manner in which liabilities, if any, resulting from the claims against AimBank in the Reagor-Dykes bankruptcy case would affect the terms of the proposed transaction.

Throughout July 2020, AIM provided Heartland with a further updates relating to the developments with respect to these claims against AimBank.

On July 21, 2020, Heartland’s board held a regularly-scheduled quarterly meeting. At the meeting, Heartland’s management updated the Heartland board on the various topics relating to the proposed acquisition of AIM, including the changes in the transaction structure, the proposed additional cash consideration to be paid to AIM shareholders, the Reagor-Dykes claims against AimBank and updated expectations regarding the closing date for the transaction.

On July 23, 2020, AIM and Heartland and their respective legal counsel held a telephone conference to discuss the term sheet that AIM provided to Heartland on July 16, 2020.

On July 24, 2020, Heartland circulated the proposed AIM/AimBank merger agreement, along with draft applications that would be filed by AimBank with the FDIC and the TDB for approval of the AIM/AimBank merger. The parties proceeded to finalize the AIM/AimBank merger agreement.

On July 31, 2020, the complaint in the Reagor-Dykes litigation was filed. The complaint sought approximately $9.0 million in damages against AimBank. After promptly informing Heartland of the Reagor-Dykes litigation, a telephone conference among AIM, Heartland and Hillworth was held on August 3, 2020 to discuss the lawsuit. Also, Heartland delivered to AIM term sheet outlining the proposed terms of the amended and restated merger agreement. The Heartland term sheet provided that the calculation of AIM’s adjusted tangible common equity would take into account the fair market value of the investment portfolio of AIM prior to the effective time, and that the threshold amount of AIM’s adjusted tangible common equity for determining an increase in the cash component of the merger consideration to be paid to AIM shareholders would be $146.0 million. In addition, Heartland proposed that the amended and restated merger agreement would contain a provision holding back a portion of the cash consideration payable to AIM shareholders in order to mitigate liabilities Heartland could incur as a result of the Reagor-Dykes litigation.

On August 4, 2020, Heartland’s counsel provided a draft of the new merger agreement among Heartland, FB&T, AIM and AimBank to AIM and its counsel. After such date, counsel to Heartland and AIM exchanged a number of drafts of the amended and restated merger agreement, and the parties negotiated the terms of the amended and restated merger agreement until it was finalized in October 2020.

On August 5, 2020, Heartland and AIM filed an Interagency Bank Merger Act Application with the FDIC relating to the AIM/AimBank merger. On the same date, Heartland also filed an application with the TDB requesting approval of the AIM/AimBank merger.

At meetings held in early August and early September, 2020, Heartland management provided detailed updates to Heartland’s board of directors regarding the status and terms of the proposed acquisition of AIM.

On August 28, 2020, Heartland filed a Current Report on Form 8-K with the SEC disclosing that AimBank was a party to the Reagor-Dykes litigation and that the closing date for Heartland’s acquisition of AIM would be delayed until the fourth quarter of 2020 or early in the first quarter 2021. On the same day, AIM sent a letter to its shareholders providing an update regarding the anticipated timetable for the completion for the transaction with Heartland and discussing other matters relating to AIM.

On September 18, 2020, subject to the receipt of the final amended and restated merger agreement and certain routine conditions, the FDIC approved the AIM/AimBank merger application and the application relating to the FB&T/AimBank merger.

On September 22, 2020, the boards of directors of AIM and AimBank held a joint meeting to consider the AIM/AimBank merger agreement. Based upon the AIM and AimBank boards’ review and consideration of the AIM/AimBank merger agreement and other relevant factors, the boards of directors of AIM and AimBank unanimously approved the AIM/AimBank merger agreement and the transactions contemplated thereby, and, on the same day, AIM and AimBank entered into the AIM/AimBank merger agreement.

On September 30, 2020, Heartland and AIM signed a letter agreement extending the “drop-dead” date of the original merger agreement from September 30, 2020 to October 31, 2020.

On October 6, 2020, Heartland, AIM, Hillworth and counsel to Heartland and AIM held a telephone conference to discuss remaining open issues relating to amended and restated merger agreement. Based on the negotiations that took place during this telephone conference, Heartland’s counsel prepared a substantially final draft of the amended and restated merger agreement and distributed it to Heartland and AIM and its counsel.

On October 8, 2020, Heartland's board of directors held a special meeting to review and discuss the amended and restated merger agreement, a copy of which had been distributed to the board in advance of the meeting in substantially final form. Heartland's board of directors received presentations from Heartland's executive management (including its General Counsel) regarding the terms of the amended and restated merger agreement and strategic and financial considerations relating to the merger. Heartland's board of directors asked a number of questions of management regarding the terms and conditions of the amended and restated merger agreement and such strategic and financial considerations, and engaged in a full discussion regarding the proposed transaction. Following this discussion, Heartland's board of directors unanimously voted to approve the amended and restated merger agreement and the transactions contemplated thereby, including the FB&T/AimBank merger, and authorized the appropriate officers of Heartland to execute and deliver the amended and restated merger agreement.

Also, on October 8, 2020, the board of directors of AIM and AimBank held a joint special meeting to consider the approval of the amended and restated merger agreement. Representatives of Hillworth, Magstar and Fenimore were in attendance. The board of directors of AIM and AimBank had been provided with materials in advance of the meeting containing information regarding the current draft of the amended and restated merger agreement and the FB&T/AimBank merger. At the meeting, the board of directors of AIM and AimBank discussed the current draft of the amended and restated merger agreement, which was in substantially final form. Representatives from Magstar rendered its opinion (which was initially rendered verbally and then confirmed in a written opinion dated October 8, 2020) to the effect that, as of October 8, 2020 and subject to the procedures followed, assumptions made, matters considered and qualifications and limitations on the review undertaken by Magstar as set forth in such opinion, the merger consideration provided was fair, from a financial point of view, to AIM’s shareholders. The AIM and AimBank boards of directors addressed a number of questions to AIM’s advisors regarding the terms and conditions of the amended and restated merger agreement and engaged in a full discussion regarding the proposed transaction.

Based upon AIM’s and AimBank’s board of directors’ review and in-depth discussion of the terms of the amended and restated merger agreement, the opinion of Magstar and other relevant factors, the board of directors of each of AIM and AimBank unanimously approved the amended and restated merger agreement, the FB&T/AimBank merger and the other transactions contemplated by the amended and restated merger agreement, and authorized the appropriate officers of AIM and AimBank to execute and deliver the amended and restated merger agreement.

By written action dated October 14, 2020, FB&T’s board approved the amended and restated merger agreement and the FB&T/AimBank merger, and authorized the appropriate officers of FB&T to execute and deliver the amended and restated merger agreement.

On October 19, 2020, Heartland, FB&T, AIM, AimBank and the shareholder representative executed the amended and restated merger agreement.

After careful consideration, at its meeting on September 22, 2020, the AIM board determined that the AIM/AimBank merger agreement and the transactions contemplated thereby, including the AIM/AimBank merger, were in the best interests of AIM and its shareholders and at its meeting on October 8, 2020, the AIM board determined that the amended and restated merger agreement and the transactions contemplated thereby, including the FB&T/AimBank merger, were in the best interests of AIM and its shareholders, and that the merger consideration to be received in the merger was fair to the AIM shareholders. Accordingly, the AIM board unanimously approved the merger agreement and the merger and unanimously recommends that the AIM shareholders vote “FOR” the AIM/AimBank merger proposal.

In reaching its decision to approve the merger and recommend the AIM/AimBank 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 AIM/AimBank merger proposal.

The fairness opinion and a summary of the underlying financial analyses of Magstar (AIM’s financial adviser) 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, AimBank, Heartland, or FB&T. You should review the copy of the fairness opinion, which is attached as Appendix D.

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 October 8, 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. This opinion supersedes any prior opinion relating to the merger described herein. 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 D 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 annual meeting on the AIM/AimBank merger proposal 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 closing 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 (including the Reagor-Dykes litigation), and with AIM’s consent and the assumption that the Reagor-Dykes litigation will be brought to final resolution prior to the Closing Date, Magstar’s opinion makes no other assumption concerning, and therefore does not consider, the possible assertion of actual or potential claims, outcomes or damages arising out of any such matters, including the aggregate holdback amount or its adequacy with respect to the Reagor-Dykes litigation or otherwise. Magstar has also assumed that none of 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. Furthermore, no opinion, counsel or interpretation was intended by Magstar on matters that require legal, accounting, regulatory or tax advice. Magstar assumed that such opinions, counsel or interpretations had been or would be obtained from appropriate professional sources. Furthermore, Magstar relied, with the consent of AIM, on the fact that AIM was assisted by legal, accounting and tax advisors, and, with the consent of AIM, relied up and assumed the accuracy and completeness of the assessment by AIM and its advisors, as to all legal, accounting and tax matters with respect to AIM, AimBank, Heartland, FB&T and the merger, including without limitation, that the merger, whether the AIM/AimBank merger and the FB&T/AimBank merger are treated collectively or, if applicable, independently, will qualify as a tax-free reorganization for U.S. 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 necessarily based upon conditions as they existed and could be evaluated on the date of such opinion and the information made available to Magstar through such date. There has been widespread disruption, extraordinary uncertainty and unusual volatility arising from the effects of the COVID-19 pandemic,

including the effect of evolving governmental interventions and non-interventions. Developments subsequent to the date of Magstar’s opinion may have affected, and may affect, the conclusion reached in Magstar’s opinion and Magstar did not and does not have an obligation to update, revise or reaffirm its opinion.

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 October 8, 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, plus any cash received in lieu of fractional shares.

Market Approach – Selected Transaction Analysis. As part of its analysis, Magstar reviewed publicly available information related to a group (a “Selected Transactions Group”) of select acquisition transactions of banks in the United States announced since March 1, 2020, in which the deal value exceeded $50 million and the target’s last-twelve-months (“LTM”) return on average assets (“ROAA”) was more than 0.85% (the “ post-COVID selected transactions analysis”). 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 Selected Transactions Group consisted of the following five transactions: