We are pleased to invite you to attend the 2022 Annual Meeting of Stockholders (the “Annual Meeting”) of Trean Insurance Group, Inc. (the “Company”) to be held virtually on Tuesday, May 17, 2022 at 10:00 a.m., Central Time. You will be able to attend and participate in the Annual Meeting online, vote your shares electronically and submit your questions during the meeting by visiting www.virtualshareholdermeeting.com/TIG2022 on the meeting date and at the time described in the accompanying Notice of Annual Meeting of Stockholders and Proxy Statement. There is no physical location for in-person attendance at the Annual Meeting.

This booklet contains the Notice of Meeting as well as the Company’s Proxy Statement associated with the Annual Meeting.

We are aware that you may be unable to attend the Annual Meeting. The proxies that we solicit give you the opportunity to vote on the matters that are scheduled to be put to a stockholder vote at the Annual Meeting regardless of whether you are able to attend. As such, whether or not you plan to attend, you can be sure that your shares are represented by promptly voting and submitting your proxy by phone or internet as described in the following materials, or, if you request that proxy materials be mailed to you, by completing, signing, dating and returning your proxy card enclosed with those materials in the postage-paid envelope provided to you.

Thank you for your investment in our Company. We look forward to your attendance virtually at the Annual Meeting.

We have designed the format of the Annual Meeting to ensure that the Company’s stockholders are afforded the same rights and opportunities to participate as they would have at an in-person meeting, through user-friendly online tools that allow stockholders to attend and take part in the Annual Meeting. After the business portion of the Annual Meeting concludes and the formal meeting is adjourned, our Chief Executive Officer, Andrew O’Brien and President and Chief Operating Officer, Julie Baron, will lead a Q&A session during which we will answer questions submitted during the meeting that are pertinent to our Company and the items being brought before our stockholders for their vote. Answers to any questions not addressed during the meeting will be posted after the meeting on the Investors section of our website.

We will have technicians ready to assist you with any technical difficulties you may have accessing the virtual meeting. If you encounter any difficulties accessing the virtual meeting during check-in or the Annual Meeting, please call the technical support number that will be posted on the virtual meeting platform log-in page.

A proxy is your legal designation of another person (the “proxy”) to vote on your behalf. By completing and returning the enclosed proxy card, you are designating each of the Chief Executive Officer, President and Chief Operating Officer, Chief Financial Officer, and General Counsel and Corporate Secretary of the Company as your proxy with the authority to vote your shares of Common Stock in the manner that you indicate through your use of one of the voting methods described in this proxy statement.

With respect to Proposal 1, you may vote FOR a director nominee or you may WITHHOLD your vote for a director nominee. Withheld votes will be treated as present at the Annual Meeting for purposes of establishing a quorum for the meeting and for purposes of the vote on the particular matter. A withheld vote will have no effect on Proposal 1.

With respect to Proposal 2, you may vote FOR, AGAINST or ABSTAIN. If you ABSTAIN from voting on Proposal 2, the abstention will have the same effect as an AGAINST vote.

You may receive multiple Notices and/or proxy cards if you hold your shares of Common Stock in different ways (e.g., joint tenancy, trusts, custodial accounts, etc.) or in multiple accounts. If your shares of Common Stock are held by a broker, bank, trustee or other nominee (i.e., in “street name”), you will receive voting instructions from your broker, bank, trustee or other nominee regarding how you may vote such shares. To ensure that all of your shares are voted, please vote each account over the Internet or by telephone, or sign and return by mail all proxy cards and instruction forms. We encourage you to have all your accounts registered in the same name and address by contacting our transfer agent, Equiniti Trust Company, telephone at 800-468-9716 or by Internet at www.shareowneronline.com. If you hold your shares through a broker, bank, trustee or other nominee, you can contact them to request consolidation.

You are qualified to receive notice of, and to vote on, the matters described in this Proxy Statement if you owned shares of Common Stock at the close of business on our Record Date of Monday, March 21, 2022.

As of March 21, 2022, there were 51,176,887 shares of Common Stock outstanding and entitled to vote. Each share of our Common Stock entitles its holder to one vote per share on all matters presented to our stockholders.

These terms describe how shares of Common Stock are held. If your shares are registered directly in your name with Equiniti Trust Company, the Company’s transfer agent, you are a “stockholder of record.” If your shares are held in the name of a brokerage, bank, trust or other nominee as a custodian, you are a “street name” holder.

You may vote either by submitting a proxy or by voting during the Annual Meeting at www.virtualshareholdermeeting.com/TIG2022. If you hold your shares in street name, you may only vote during the meeting if you properly request and receive a legal proxy in your name from the nominee that holds your shares as a matter of record.

The method of voting by proxy differs depending on whether you are viewing this proxy statement online or reviewing a paper copy.

If you hold your shares in street name, your broker, bank, trustee or other nominee will provide you with materials and instructions for voting your shares, which may allow you to use the internet or a toll-free telephone number to vote your shares.

Whether or not you plan to attend the Annual Meeting, we urge you to vote promptly using one of the methods described in these proxy materials. We encourage you to vote by telephone or online since these methods immediately record your vote and allow you to confirm that your votes have been properly recorded. Telephone and online votes must be received by 11:59 p.m., Eastern Time, on May 16, 2022.

If you are a stockholder of record and you give your proxy pursuant to this solicitation but without indicating how you want your shares to be voted, the Chief Executive Officer, President and Chief Operating

Officer, Chief Financial Officer, and General Counsel and Corporate Secretary of the Company will vote your shares in accordance with the Board’s recommendations for the Proposals listed above and in the discretion of the named proxies regarding any other matters properly presented for a vote at the Annual Meeting.

If you are a street name holder and do not provide the broker, bank, trustee or other nominee that holds your shares with specific voting instructions, the broker, bank, trustee or other nominee that holds your shares may generally vote on “routine” matters without instructions from you. We expect the ratification of the appointment of Deloitte & Touche LLP as the Company’s independent registered public accounting firm for the fiscal year ending December 31, 2022 (Proposal 2) to be the only proposal that is considered a “routine” matter. Accordingly, if your shares are held through a broker, bank, trust or other nominee, that person will have discretion to vote your shares on Proposal 2 if you fail to provide voting instructions.

On the other hand, your broker, bank, trustee or other nominee is not entitled to vote your shares on any “non-routine” matters if it does not receive instructions from you on how to vote. The election of Class II directors (Proposal 1) will be considered a “non-routine” matter. Thus, if you do not give your broker, bank, trustee or other nominee specific instructions on how to vote your shares with respect to Proposal 1, your broker, bank, trustee or other nominee will inform the Inspectors of Election that it does not have the authority to vote your shares on that proposal. This is generally referred to as a “broker non-vote.” A broker non-vote may also occur if your broker, bank, trustee or other nominee fails to vote your shares for any reason.

The presence, in person or represented by proxy, of the holders of a majority of the shares of Common Stock issued and outstanding on the Record Date for the Annual Meeting will constitute a quorum for the transaction of business at the Annual Meeting.

A “vote withheld,” in the case of the election of Class II directors (Proposal 1), or an “abstention,” in the case of the proposal for the ratification of the appointment of Deloitte & Touche LLP as the Company’s independent registered public accounting firm for the fiscal year ending December 31, 2022 (Proposal 2), represents a stockholder’s affirmative choice to decline to vote on a proposal. Votes withheld and abstentions are deemed to be “present” at the Annual Meeting and are counted for quorum purposes. Votes withheld have no effect on Proposal 1. Abstentions have the same effect as a vote against Proposal 2. Broker non-votes, if any, while counted for general quorum purposes, will have no effect on the voting results for any matter other than Proposal 2.

If you are a stockholder of record, you may revoke your proxy by doing one of the following:

If you hold your shares in street name, your broker, bank, trustee or other nominee will provide you with instructions on how to revoke your proxy.

Representatives from Broadridge Financial Solutions, Inc. will count the votes and serve as our Inspectors of Election. The Inspectors of Election will also determine whether a quorum is present. The Inspectors of Election will be present at the Annual Meeting.

The Company pays the costs of soliciting proxies. Upon request, the Company will reimburse brokers, banks, trustees or their other nominees for reasonable expenses incurred by them in forwarding proxy materials to beneficial owners of shares of Common Stock. In addition, certain of our directors, officers, and employees may aid in the solicitation of proxies. These individuals will receive no compensation in addition to their regular compensation.

No. As stated above, in addition to mailing these proxy materials, certain of our directors, officers and employees may solicit proxies by telephone, e-mail or personal contact. These directors, officers and employees will not be specifically compensated for doing so.

The SEC’s rules permit us to deliver a single set of proxy materials to one address shared by two or more of our stockholders. This delivery method is referred to as “householding” and can result in significant cost savings. To take advantage of this opportunity, we have delivered only one set of proxy materials to multiple stockholders who share an address, unless we received contrary instructions from the impacted stockholders prior to the mailing date. We agree to deliver promptly, upon written or oral request, a separate copy of the proxy materials, as requested, to any stockholder at the shared address to which a single copy of those documents was delivered. If you prefer to receive separate copies of the proxy materials, please contact our General Counsel and Corporate Secretary, Patricia A. Ryan, at (952) 974-2230 or in writing at 150 Lake Street West, Wayzata, MN 55391.

If you are currently a stockholder sharing an address with another stockholder and wish to receive only one copy of future proxy materials for your household, please contact our General Counsel and Corporate Secretary at the above phone number or address.

Our business and affairs are managed under the direction of our Board of Directors. The number of directors is fixed by our Board of Directors, subject to the terms of our Amended and Restated Certificate of Incorporation and Amended and Restated By-laws. Our Board of Directors currently consists of seven directors.

We have structured our corporate governance in a manner that we believe closely aligns our interests with those of our stockholders. Notable features of our corporate governance structure include the following:

Pursuant to the Nasdaq Marketplace Rules, “controlled companies” are companies of which more than 50% of the outstanding voting power is held by an individual, group or another company. Following our initial public offering (“IPO”) in July 2020, affiliates of Altaris Capital Partners, LLC (the “Altaris Funds”) collectively controlled more than 50% of the voting power of our Common Stock and thus were able to elect our entire Board of Directors. Accordingly, our Board of Directors determined that we were a “controlled company” and were therefore able to take advantage of exemptions from certain corporate governance requirements under the Nasdaq rules that would otherwise have applied. Specifically, we were not required to have (i) a majority of our Board of Directors comprised of independent directors or (ii) a nominating and corporate governance and/or compensation committee comprised entirely of independent directors. We availed ourselves of certain of these exemptions following our IPO until May 2021.

In May 2021, the Altaris Funds conducted a secondary offering of an aggregate of 4,250,498 shares of Common Stock. The sale by the Altaris Funds of these shares resulted in their ownership falling below 50% of our outstanding Common Stock upon the closing of the secondary offering on May 24, 2021, and, accordingly, we ceased to qualify as a “controlled company” as of that date. As a result of this change, pursuant to the transition period provided by the rules of Nasdaq, our Compensation, Nominating and Corporate Governance Committee must be fully independent and a majority of the members of our Board of Directors must be independent within one year following our loss of controlled company status. As of April 5, 2022, we are in compliance with these requirements. The controlled company exemption does not modify the independence requirements for audit committees, and we remain in compliance with the requirements of the Rule 10A-3 under the Exchange Act and the Nasdaq rules that require full audit committee independence.

Our Board of Directors reviews at least annually whether each of our directors and director nominees meets the independence requirements of the applicable provisions of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and the applicable rules of Nasdaq. To determine whether our directors and director nominees are independent, the Board evaluates any relationships of our directors and director nominees with the Company and the members of the Company’s management against these independence requirements, provisions and rules. In making its independence determinations, the Board broadly considers all relevant facts and circumstances, including the responses of directors and director nominees to a questionnaire that solicited information about their relationships. The Board also considers any relationships between the Company and other organizations for which our directors serve as directors or with respect to which our directors are otherwise affiliated, and considers whether any director has a material relationship with us that could compromise that director’s ability to exercise independent judgment in carrying out that director’s responsibilities.

The Board has determined that each of the following five of our non-employee directors satisfies the independence standards and does not otherwise have a material relationship with the Company (either directly or

as an officer, employee, shareholder or partner of an organization that has a relationship with the Company) that would impair his or her independence, such that each of them qualifies as independent under the applicable rules of Nasdaq and the SEC:

The independent members of our Board meet regularly in executive sessions, typically at each regularly scheduled Board meeting, and otherwise as needed.

The Board regularly considers the appropriate leadership structure for the Company. The Board has concluded that the Company and its stockholders are best served by the Board retaining discretion to determine whether the same individual should serve as both Chief Executive Officer and Chairman of the Board, or whether the roles should be separated. Following our IPO, the Board determined to implement a leadership structure under which Andrew M. O’Brien has served as our Chief Executive Officer and Daniel G. Tully has served as our Chairman of the Board. As previously announced, effective in July 2022 Mr. O’ Brien will step down as our Chief Executive Officer, and Julie A. Baron will be promoted to that position and will join the Board of Directors. At that time, Mr. Tully will also step down as Chairman of the Board, and Mr. O’Brien will assume the role of Executive Chairman of the Board. The Board believes this new leadership structure, with Mr. O’Brien serving as Executive Chairman and Ms. Baron as Chief Executive Officer, will best serve the interests of the Company and our stockholders following this important leadership transition.

One of the key functions of the Board of Directors is to provide informed oversight of our risk management process. The Board administers this oversight function directly, with support from its two standing committees, the Audit Committee and the Compensation, Nominating and Corporate Governance Committee, each of which addresses risks specific to its respective areas of oversight. In particular, the Audit Committee has the responsibility to consider and discuss our major financial risk exposures and the steps our management has taken to monitor and control these exposures. The Audit Committee also monitors compliance with legal and regulatory requirements. Our Compensation, Nominating and Corporate Governance Committee assesses and monitors whether any of our compensation policies and programs have the potential to encourage unnecessary or excessive risk-taking, and reviews and discusses the relationship between risk management policies and practices, corporate strategy and the Company’s compensation arrangements.

The Board of Directors and its committees are supported in their oversight of our risk management by a separate enterprise risk management (“ERM”) committee consisting of seven senior executives, each of whom represents a critical operating unit of the Company. Our Board of Directors, ERM committee and senior management have identified five key risk areas for oversight within the ERM framework. The five key risk areas are credit risk, market risk, underwriting risk, strategic risk and operational risk. Within each key risk, we have identified specific risk sub-categories leading to the identification and analysis of more granular risks. Through a documented analytical process, the ERM committee continually reviews and evaluates these risks to monitor due to their potential impact on our businesses and periodically reports its findings to the Board of Directors and its committees. Our Board of Directors believes that this overall structure and analytical process creates effective risk identification, appetite determination, controls, oversight, and management for our Company.

Our Board of Directors has two standing committees: the Audit Committee and the Compensation, Nominating and Corporate Governance Committee. Each committee operates under a charter approved by our Board of Directors. A copy of each charter is posted on the “Investor Relations —Governance — Document & Charters” section of our website, www.trean.com. Information contained on our website is not a part of this proxy statement and the inclusion of our website address in this proxy statement is an inactive textual reference only.

Audit Committee.

Our Audit Committee consists of Mr. Mayotte, who serves as the chair of the Audit Committee, Ms. Chaput, Mr. Jones and Mr. Smith, who all qualify as independent directors under the corporate governance standards of Nasdaq and the independence requirements of Rule 10A-3 under the Exchange Act. Our Board of Directors has determined that each of Mr. Mayotte and Ms. Chaput qualifies as an “audit committee financial expert” as such term is defined in Item 407(d)(5) of Regulation S-K. The Audit Committee will assist our Board of Directors in fulfilling its oversight responsibilities relating to:

In so doing, the Audit Committee is responsible for maintaining free and open communication between the committee, our independent registered public accounting firm and our management. In this role, the Audit Committee is empowered to investigate any matter brought to its attention with full access to all books, records, facilities and personnel of Trean Insurance Group, Inc. and has the power to retain outside counsel or other experts for this purpose.

The Audit Committee has direct responsibility for the appointment, compensation, retention and oversight of our independent registered public accounting firm. The Audit Committee meets in executive session with representatives of our independent registered public accounting firm at least quarterly.

Compensation, Nominating and Corporate Governance Committee.

Our Compensation, Nominating and Corporate Governance Committee consists of Mr. Jones, who serves as the chair, Ms. Chaput, Mr. Smith and Mr. Tully, who all qualify as independent directors under the corporate governance standards of Nasdaq applicable to compensation committee members. The committee assists our Board of Directors with reviewing the performance of our management in achieving corporate goals and objectives and assuring that our executives are compensated effectively in a manner consistent with our strategy, competitive practice and the requirements of appropriate regulatory bodies. Toward that end, the Compensation, Nominating and Corporate Governance Committee reviews and recommends to the full Board director and executive officer compensation, incentive compensation and equity-based compensation plans, and employee benefit plans, among other responsibilities. The Compensation, Nominating and Corporate Governance Committee also assists our Board of Directors by:

Pursuant to its charter, the Compensation, Nominating and Corporate Governance Committee has the authority to engage its own executive compensation consultants and legal advisors. In 2021, the Compensation, Nominating and Corporate Governance Committee engaged F.W. Cook & Co. (“FW Cook”) as its compensation consultant to assist in determining the amount of executive and director compensation in 2021, including providing competitive market data relating to executive and director compensation, providing guidance on compensation program structure and advising on grants under the Trean 2020 Omnibus Equity Plan. As required under the Nasdaq listing rules, the Compensation, Nominating and Corporate Governance Committee has assessed the independence of FW Cook pursuant to applicable SEC and Nasdaq rules, including, but not limited to, those set forth in Rule 5605(d)(3)(D) of the Nasdaq Stock Market Rules.

Our Board of Directors and its committees meet periodically during the year, hold special meetings as needed and act by written consent from time to time as deemed appropriate. During 2021, our Board of Directors held four meetings, the Audit Committee of our Board of Directors held four meetings, and the Compensation, Nominating and Corporate Governance Committee held two meetings. During that span, no director attended fewer than 75% of the aggregate of (a) the total number of meetings of our Board of Directors and (b) the total number of meetings held by all committees of our Board of Directors on which such director served.

All of our then-current directors attended the annual meeting of stockholders that our Company held virtually in May of 2021. Each of our directors is encouraged to attend our annual meetings of stockholders. Accordingly, we expect most, if not all, of our directors to be in attendance at the Annual Meeting.

Our Board has adopted a Code of Business Conduct and Ethics that applies to our directors, officers and employees. A current copy of the code is posted on our website, which is located at www.trean.com. Any amendments or waivers to our code of conduct will be disclosed on our website promptly following the date of such amendment or waiver.

Copies of the current versions of our governance documents, along with current versions of our Code of Business Conduct and Ethics and Board committee charters are posted on the “Investor Relations — Governance — Document & Charters” section of our website, www.trean.com. These items are also available in print to any stockholder who requests them by writing to Trean Insurance Group, Inc., Investor Relations, at 150 Lake Street West, Wayzata, MN 55391, Attn: General Counsel. In addition, the SEC maintains an Internet site at www.sec.gov that contains our reports, proxy and information statements and other information we file electronically, including the current version of our Amended and Restated Certificate of Incorporation and Amended and Restated By-laws filed as exhibits to our Annual Report on Form 10-K.

Pursuant to our director compensation policy, each of our non-affiliated and non-employee directors receives the following compensation for service on our Board of Directors:

Stockholders?” The Compensation, Nominating and Corporate Governance Committee will conduct the same analysis that it conducts with respect to director nominees or other potential candidates recommended by a Board member, management or other source in order to evaluate any director nominations properly submitted by a stockholder.

If a stockholder seeks to have a proposal included in the Company’s Proxy Statement for the 2023 Annual Meeting of Stockholders pursuant to Rule 14a-8 under the Exchange Act, the proposal must be received by the Company no later than December 5, 2022 and be submitted in accordance with applicable rules and regulations. Such proposals must be delivered to Trean Insurance Group, Inc., at 150 Lake Street West, Wayzata, MN 55391, Attn: Secretary.

If a stockholder seeks to bring business before our annual meeting that is not the subject of a proposal submitted for inclusion in the proxy statement under Rule 14a-8, or wishes to nominate an individual to serve as a director, such stockholder must comply with the advance notice procedures described in the Company’s Amended and Restated By-laws. In addition to satisfying the foregoing requirements under the Company’s Amended and Restated Bylaws, to comply with the universal proxy rules (once effective), stockholders who intend to solicit proxies in support of director nominees other than the Company’s nominees must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act no later than March 20, 2023.

For the Company’s 2023 Annual Meeting of Stockholders, the Secretary must receive notice of such business or director nomination no earlier than January 18, 2023 and no later than February 17, 2023 or, if the annual meeting is called for a date that is not within thirty (30) days before or more than sixty (60) days after such anniversary date, of the immediately preceding Annual Meeting, the notice must be received no later than the close of business on the tenth (10th) day following the day on which such notice of the date of the Annual Meeting was mailed or such public disclosure of the date of the Annual Meeting was made.

Stockholder proposals with respect to such business or director nomination must be in proper written form and must meet the detailed disclosure requirements set forth in the Amended and Restated By-laws of the Company. The Company’s Amended and Restated By-laws also require that stockholder proposals concerning the nomination of directors provide additional disclosure regarding any nominee, including but not limited to name, age, business address and residence address, principal occupation or employment, class and number of shares of stock of the Company owned beneficially or of record by the nominee or any affiliates, whether and the extent to which any derivative instrument, swap, option, warrant, short interest, hedge or profit interest or other transaction has been entered into by or on behalf of such person, or any affiliates or associates of such person, with respect to stock of the Company, whether any other transaction, agreement, arrangement or understanding has been made by or on behalf of such nominee, the effect of which is to mitigate loss to, or to manage risk or benefit of stock price changes for, such nominee, and any other information that would be required to be disclosed in a proxy statement pursuant to Section 14 of the Exchange Act.

Notice must be accompanied by a written consent of each proposed nominee to being named as a nominee and to serving as a director if elected. The Company may require any proposed nominee to furnish such other information as it may reasonably deem necessary to determine the eligibility of such proposed nominee to serve as a director of the Company and to determine the independence of such director under the Exchange Act and rules and regulations thereunder and applicable stock exchange rules.

The non-employee directors may be contacted by any stockholder or other interested party in the following manner:

Our business affairs are managed under the direction of our Board, which is currently comprised of seven members, and, as previously announced, is expected to be expanded to eight members when Julie A. Baron joins the Board as a Class III director in connection with her promotion to Chief Executive Officer effective in July 2022. Our Board is divided into three classes with staggered three (3)-year terms. The Board has nominated Andrew M. O’Brien and Steven B. Lee for election at the Annual Meeting, each to serve as a Class II director until the 2025 annual meeting of stockholders or until his or her successor has been duly elected and qualified. The following table sets forth the names, ages as of March 31, 2022, and certain other information for each of the nominees and for each of the directors whose terms do not expire at the Annual Meeting.

Mr. O’Brien has served as the Chief Executive Officer and as a director since he founded the Company in 1996. He served as our President from 1996 until June 2021. Prior to founding our Company, Mr. O’Brien served as a General Partner, Executive Vice President and director of E.W. Blanch Company. Mr. O’Brien has

also served as a director of the Health Care Insurance Facility, First Dakota Indemnity Company and SAFE, Inc., a holding company for an accident and health insurer. Mr. O’Brien holds a B.A. in Sociology from the University of Minnesota, a J.D. from the University of Minnesota Law School and a Chartered Property Casualty Underwriter designation. The Board of Directors has concluded that Mr. O’Brien’s extensive knowledge of Company operations, finances, strategies and industry make him well-qualified to serve as Chief Executive Officer and on the Board of Directors of the Company.

Mr. Lee has served as a director of the Company since December 1996. Mr. Lee also served as the Senior Vice President for Trean Reinsurance Services, LLC from December 2016 through December 2020. Mr. Lee has 38 years of experience in the reinsurance and insurance industry focusing on workers’ compensation, casualty and professional liability. Mr. Lee holds a B.A. in Psychology from St. Olaf College, an M.B.A. from the University of Wisconsin and a J.D. from the Mitchel Hamline School of Law. Our Board of Directors has concluded that Mr. Lee’s industry experience and expertise relating to workers’ compensation, casualty and professional liability make him well-qualified to serve on the Board of Directors of the Company.

Mr. Jones has served as a director of Trean since 2008 and has been in the insurance business for 46 years. The majority of his experience has been in the specialty lines insurance market. After starting his career as a claims adjuster with a standard lines insurer, Mr. Jones has extensive specialty lines experience as a wholesale broker and in underwriting, product management and executive positions, including as the chief executive officer of two specialty lines insurers for approximately ten years. Mr. Jones has served in various company and industry board roles including associations such as NAPSLO, PCI and the MN Insurance Federation, including serving as the consulting education director for NAPSLO after many years as a volunteer instructor for the organization. Mr. Jones currently conducts select strategic consulting and executive coaching for clients in the reinsurance, alternative and surplus lines marketplaces, including an ongoing consulting role with WSIA, the successor organization to NAPSLO. Mr. Jones holds a B.S. in Administration of Justice from Southern Illinois University and a M.Ed. in Adult Learning & Curriculum from Central Michigan University. The Board of Directors has concluded that Mr. Jones’s extensive executive and operational experience and knowledge of the insurance industry make him well-qualified to serve on the Board of Directors of the Company.

Mr. Mayotte has served as a director of the Company of since July 2021. Mr. Mayotte founded Oasis Outsourcing Holdings Inc. and served as the Chief Financial Officer from July 2016 to December 2018, when it was acquired by Paychex, Inc. (Nasdaq: PAYX). Mr. Mayotte currently serves as the President of Oasis Outsourcing, a subsidiary of Paychex, Inc. Mr. Mayotte has extensive experience in workers’ compensation, a core product of Oasis Outsourcing Holdings Inc. Mr. Mayotte holds a B.A. in Finance from Emory University. Our Board of Directors has concluded that Mr. Mayotte’s extensive finance experience and his workers’ compensation experience make him well-qualified to serve on the Board of Directors of the Company.

Mr. Tully has served as a director of the Company since July 2015 and also serves as the Chairman of our Board of Directors. Mr. Tully is a Managing Director at Altaris Capital Partners, LLC (“Altaris”), which he

co-founded in 2002. Mr. Tully has extensive experience serving on audit, compensation, and compliance committees. Prior to the formation of Altaris, Mr. Tully held various positions with Merrill Lynch, including serving as the firm’s global head of healthcare equity capital markets and as a member of Merrill Lynch’s private equity and investment banking groups. Mr. Tully has also served as a director of Tivity Health, Inc. (Nasdaq: TVTY), a publicly traded provider of health solutions, from August 2019 to September 2020. Mr. Tully received a B.S. in Economics from the University of Pennsylvania, Wharton Undergraduate Program. The Board of Directors has concluded that Mr. Tully’s detailed knowledge of our operations, finances, strategies and industry make him well-qualified to serve as Chairman of the Board of Directors of the Company.

Ms. Chaput has served as a director of the Company since August 2020. Since May 2018, Ms. Chaput has served as a member of the board of directors of Clearwater Compliance LLC, a healthcare cybersecurity and compliance company. From December 2011 to May 2018, Ms. Chaput served as Chief Financial Officer and Chief Compliance Officer of Clearwater Compliance LLC. From October 2001 to December 2011, Ms. Chaput served as Executive Vice President and Chief Financial Officer of Healthways, Inc. (now known as Tivity Health, Inc. (Nasdaq: TVTY)). While at Healthways, Ms. Chaput led the global finance organization, including acquisitions, legal, treasury activities, accounting, and tax planning. Ms. Chaput received a B.A. in Mathematics from Russell Sage College and an M.B.A., summa cum laude, from State University of New York, Albany. She is also a graduate of the General Electric Financial Management Program. Our Board of Directors has concluded that Ms. Chaput’s extensive finance and accounting experience, and her background as a senior executive with publicly traded companies, make her well-qualified to serve on the Board of Directors of the Company.

Mr. Smith has served as a director of the Company since March 2022. Mr. Smith has been a Managing Director, Investment Banking with Duff and Phelps, LLC, an investment banking firm that provides mergers & acquisitions, valuation, corporate finance and other services since December 2016. Mr. Smith provides services in the area of healthcare mergers and acquisitions advisory and is based in Minneapolis. Mr. Smith has more than 25 years of healthcare experience as a mergers and acquisitions investment banker and executive operating officer. He has expertise in assisting public and private companies as well as private equity firms. Prior to joining Duff & Phelps, Mr. Smith was a Managing Director with BMO Capital Markets (formerly Greene Holcomb and Fisher) where he focused on healthcare mergers and acquisitions. Before that, he was a member of the medical device investment banking team at Piper Jaffray in Minneapolis. Early in his career, Mr. Smith served as an executive officer for a number of medical technology companies, including DGIMED Ortho, Vital Images, Thermonix and Image-Guided Neurologics. He has also served on the board of directors of Delta Dental of Minnesota, MGC Diagnostics (formerly Angeion Corp) and currently serves on the board of directors of Intricon Corp (Nasdaq: IIN) and Nortech Systems Incorporated (Nasdaq: NSYS). Mr. Smith received an MBA from the Wharton School of the University of Pennsylvania and a B.S. in electrical engineering from the University of Florida. The Board of Directors has concluded that Mr. Smith’s investment experience, and his background working with publicly traded companies make him well-qualified to service on the Board of Directors of the Company.

There have been no material legal proceedings that would require disclosure under the federal securities laws that are material to an evaluation of the ability or integrity of our directors or executive officers, or in which any director, officer, nominee or principal stockholder, or any affiliate thereof, is a party adverse to us or has a material interest adverse to us.

Andrew M. O’Brien has served as Chief Executive Officer and as one of the directors since he founded our Company in 1996. Mr. O’Brien’s employment experience and professional background are set forth above under the heading “Members of the Board of Directors.” As previously announced, Mr. O’Brien will step down as our Chief Executive Officer and assume the role of Executive Chairman in connection with a leadership transition to be effective in July 2022.

Julie A. Baron has served as our President and Chief Operating Officer since June of 2021. From March of 2015 through June of 2021, Ms. Baron served as the Treasurer and Chief Financial Officer of the Company. From November 2007 to March 2015, Ms. Baron served as the Controller for Benchmark. Prior to joining our Company, Ms. Baron was a controller for Ala Carte Broker Services, LLC, a mortgage broker and title company in the Twin Cities. Ms. Baron holds a B.S. in Accounting from Arizona State University and is a Certified Public Accountant (inactive). As previously announced, Ms. Baron will assume the role of Chief Executive Officer of the Company and will join the Board of Directors effective July 2022 in connection with a leadership transition.

Nicholas J. Vassallo has served as our Treasurer and Chief Financial Officer since June of 2021. From May of 2020 to June of 2021, Mr. Vassallo served as Chief Accounting Officer of the Company. Prior to joining our Company, Mr. Vassallo served as Chief Accounting Officer for iMedia Brands, Inc. from May 2018 to October 2019 and as Senior Vice President – Corporate Controller since October 2015 and Vice President – Corporate Controller since 2001, having first joined iMedia Brands, Inc. as director of financial reporting in October 1996. Mr. Vassallo began his career with Arthur Anderson LLP, where he spent eight years in its audit practice group. Mr. Vassallo holds a B.S. in Accounting from St. John’s University and is a Certified Public Accountant (inactive).

Patricia A. Ryan has served as our General Counsel and Corporate Secretary since September of 2021. Prior to joining the Company, Ms. Ryan served as Chief Legal Officer and Head of Employee Engagement for HDI Global Insurance Company. Prior to HDI, Ms. Ryan was Executive Vice President and General Counsel of American Overseas Group, a Bermuda domiciled insurance holding company, as well as an Officer and Director of its operating subsidiaries. Prior to joining the Company, Ms. Ryan was Senior Director at Allianz and Assistant Vice President at QBE Insurance Company. Ms. Ryan is currently a member of the Board of Directors of Spinnaker Insurance Company. Ms. Ryan holds a BA in Economics and History from the University of Illinois in Urbana Champaign, and a JD from Loyola University of Chicago.

Matthew J. Spencer has served as our Chief Information & Security Officer since October 2018. Mr. Spencer served as our Vice President of Business Technology from April 2015 to October 2018. Prior to joining our Company, Mr. Spencer served as the Senior Project Office Manager for MMIC Insurance, Inc. from July 2013 to March 2015. Mr. Spencer holds a B.S. in Quantitative Methods in Computer Science and a B.A. in Business Administration and Management from the University of St. Thomas.

Meeting do not ratify the appointment of Deloitte as our independent registered public accounting firm for the fiscal year ending December 31, 2022, the selection of our independent registered public accounting firm will be reconsidered by the Audit Committee. Abstentions will have the same effect as a vote against this proposal.

Each of our named executive officers was provided with the following material elements of compensation in the year ended December 31, 2021:

Each of our named executive officers received a fixed base salary. The base salary payable to each named executive officer is intended to provide a fixed component of compensation reflecting the executive’s skill set, experience, role and responsibilities. Each named executive officer’s base salary for the fiscal years ended December 31, 2021 and December 31, 2020 is listed in the “Fiscal Year 2021 Summary Compensation Table” above.

Annual cash bonuses are a key component of our executive compensation strategy and are designed to motivate our executive officers to meet our strategic business and financial objectives generally and our annual financial performance targets in particular. Each of our named executive officers is entitled to receive an annual cash incentive bonus as recommended by our Compensation, Nominating and Corporate Governance Committee and approved by the Board of Directors. The Board of Directors, with the recommendation of the Compensation, Nominating and Corporate Governance Committee, has historically awarded cash incentive awards following each fiscal year. For fiscal 2021, the Compensation, Nominating and Corporate Governance Committee established dual performance metrics for our annual cash incentive program based on the Company’s achievement of gross written premiums and loss ratio for the fiscal year. The annual incentive bonuses actually awarded to each named executive officer under this program were determined by our Compensation, Nominating and Corporate Governance Committee in consultation with both our Chief Executive Officer (other than with respect to his own compensation) and FW Cook and recommended to the Board of Directors for approval. The determination involved an analysis of the Company’s performance relative to the performance metrics established for fiscal 2021 by the Compensation, Nominating and Corporate Governance Committee, as well as such other factors as the Compensation, Nominating and Corporate Governance Committee deemed appropriate for consideration in its discretion, including the performance of the individual officer and his or her contributions to the Company. We anticipate continuing to provide our named executive officers with an opportunity to earn an annual cash incentive bonus, based on individual and Company goals.

In connection with our IPO, we adopted the Trean Insurance Group, Inc. 2020 Omnibus Incentive Plan (the “2020 Plan”), pursuant to which we may grant cash and equity-based incentive awards to selected officers, employees, non-employee directors, independent contractors and consultants, to strengthen their commitment, motivate them to faithfully and diligently perform their responsibilities and to attract and retain competent and dedicated persons who are essential to the success of our business and whose efforts will impact our long-term growth and profitability. Certain employees of the Company and its affiliates, including Ms. Baron and Mr. Spencer received equity awards under the 2020 Plan in connection with our IPO and in 2021 as part of the Company’s initial long-term equity incentive program. These awards during 2020 and 2021 consisted of equal components of stock options and three types of restricted stock units: time-based restricted stock units (“RSUs”) with a three-year vesting period, performance stock units (“PSUs”) for shares of Common Stock that may be earned in accordance with the Company’s achievement of pre-established target threshold goals for total gross written premiums over a three-year performance period, and market stock units (“MSUs”) for shares of Common Stock that may be earned in accordance with the Company’s cumulative total shareholder return over a three-year performance period. Under this program, Ms. Baron received stock options, time-based RSUs, PSUs and MSUs that each represent (at target, for the PSUs and MSUs) 7,039 shares of Common Stock, or a total of 28,155 shares of Common Stock and Mr. Spencer received stock options, time-based RSUs, PSUs and MSUs that each represent 4,224 shares of Common Stock, or a total of 16,894 shares of Common Stock. Mr. O’Brien did not receive awards under this program.

Retirement and Employee Benefits Plans. All employees are eligible to participate in broad-based and comprehensive employee benefit programs, including medical, dental, vision, life and disability insurance and a 401(k) plan with matching contributions. Our named executive officers are eligible to participate in these plans

on the same basis as our other employees. We do not sponsor or maintain any deferred compensation or supplemental retirement plans in addition to our 401(k) plan. The 401(k) matching contributions, including both a 3% employer safe harbor contribution and an employer matching contribution, earned by each named executive officer in the fiscal years ended December 31, 2021 and December 31, 2020, are included in the “Fiscal Year 2021 Summary Compensation Table” under “All Other Compensation.” Long-term care payments, pursuant to which we pay for a portion of long-term care insurance premiums, are available to certain executives, including the named executive officers.

No Tax Gross-Ups. We do not make gross-up payments to cover our named executive officers’ personal income taxes that may pertain to any of the compensation or perquisites paid or provided by our Company.

Employment Agreements. We currently do not have any employment agreements with our named executive officers.

The Company’s insider trading policy prohibits directors and officers from directly or indirectly engaging in trading in put or call options for the Company’s common stock and hedging against future declines in the market value of the Company’s common stock through the purchase of financial instruments designed to offset such risk and from pledging the Company’s securities as collateral for margin and other loans.

As of the date of this Proxy Statement, the Board has not received notice of, and does not intend to propose, any other matters for stockholder action. However, if any other matters are properly brought before the Annual Meeting, it is intended that the persons voting the accompanying proxy will vote the shares represented by the proxy in accordance with their best judgment.