TIG Trean Insurance Group Inc

We are pleased to invite you to attend the 2021 Annual Meeting of Stockholders (the “Annual Meeting”) of Trean Insurance Group, Inc. (the “Company”) to be held virtually on Tuesday, May 18, 2021 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/TIG2021 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 President and Chief Executive Officer, Andrew O’ Brien, 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.

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 22, 2021.

As of March 22, 2021, there were 51,148,782 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/TIG2021. 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 17, 2021.

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, Chief Financial Officer, Corporate

Secretary and General Counsel 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, 2021 (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 only 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 I 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 I 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, 2021 (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.

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 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, our Board of Directors has determined that we are a “controlled company.” “Controlled companies” under the Nasdaq rules are companies of which more than 50% of the outstanding voting power is held by an individual, group or another company. At present, affiliates of Altaris Capital Partners, LLC (the “Altaris Funds”) collectively control more than 50% of the voting power of our Common Stock and thus are able to elect our entire Board of Directors. Accordingly, we are able to take advantage of exemptions from certain requirements under the Nasdaq rules that would otherwise apply. Specifically, we are 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 that is comprised entirely of independent directors. We avail ourselves of these exemptions.

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 the following three of our non-employee directors satisfy the independence standards and do 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 their 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. Currently, the Board believes that our existing leadership structure, under which Andrew M. O’Brien serves as our President and Chief Executive Officer and Daniel G. Tully serves as our Chairman of the Board, is effective.

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 one independent member of our Board of Directors and seven senior executives, each of whom represents a critical operating unit of the Company, including our Chief Executive Officer. 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 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 and Mr. Jones, 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. Ellison, who serves as the chair, Mr. Tully and Mr. Jones. 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 approves 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. The Compensation, Nominating and Corporate Governance Committee determined not to engage a compensation consultant in determining the amount of executive or director compensation in 2020.

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 the portion of 2020 following our initial public offering, our Board of Directors held two meetings, the Audit Committee of our Board of Directors held two meetings, and the Compensation, Nominating and Corporate Governance Committee held no 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.

Our upcoming Annual Meeting will be the first annual meeting of stockholders that our Company has held since we became a publicly traded company following the completion of our initial public offering in July 2020 (the “IPO”). 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 of Directors 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:

We also reimbursed all directors (including affiliated and employee directors) for reasonable out-of-pocket expenses they incur in connection with their service as directors.

The following table summarizes the aggregate fees earned or paid and the value of equity-based awards earned by our non-employee directors in 2020:

The Compensation, Nominating and Corporate Governance Committee has responsibility for identifying, recruiting and evaluating candidates to fill positions on the Board, including persons suggested by stockholders or others. The Compensation, Nominating and Corporate Governance Committee reviews the background and qualifications of individuals being considered as director candidates. Among the qualifications considered in the

selection of candidates, the Compensation, Nominating and Corporate Governance Committee considers a variety of relevant attributes and criteria of candidates, including experience, skills, expertise, diversity, personal and professional integrity, character, business judgment, time availability in light of other commitments (including the number of public company boards on which a director candidate serves), dedication, conflicts of interest and such other relevant factors that the Compensation, Nominating and Corporate Governance Committee considers appropriate in the context of the needs of the Board. The Compensation, Nominating and Corporate Governance Committee recommends to the Board the director nominees for election by the stockholders or appointment by the Board, as the case may be.

The Company is party to a director nomination agreement (the “Director Nomination Agreement”) with the Altaris Funds. So long as the Altaris Funds collectively own 35% or more of our outstanding Common Stock, the Altaris Funds will have the right (but not the obligation) to nominate three individuals to our Board of Directors; so long as the Altaris Funds collectively own 20% or more but less than 35% of our outstanding Common Stock, the Altaris Funds will have the right (but not the obligation) to nominate two individuals to our Board of Directors; and so long as the Altaris Funds collectively own 10% or more but less than 20% of our outstanding Common Stock, the Altaris Funds will have the right (but not the obligation) to nominate one individual to our Board of Directors. Subject to limited exceptions, we will include these nominees in the slate of nominees recommended to our stockholders for election as directors.

The Compensation, Nominating and Corporate Governance Committee will consider candidates for election to our Board of Directors who are recommended by stockholders, provided such recommendations are submitted in accordance with the procedures established by the Company’s bylaws, which are further described below in “How can I submit a stockholder proposal or nominate a director for the 2022 Annual Meeting of 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 2022 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 7, 2021 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.

For the Company’s 2022 Annual Meeting of Stockholders, the Secretary must receive notice of such business or director nomination no earlier than January 18, 2022 and no later than February 17, 2022 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 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:

Mr. Tully has served as one of our directors 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. Our 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 our Board of Directors.

Ms. Chaput has served as one of our directors 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 January 2012 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 our Board of Directors.

Mr. Ellison has served as one of our directors since July 2015. Mr. Ellison is a Managing Director at Altaris, where he has held various positions since August 2007, and has extensive experience serving on audit, compensation, and compliance committees. Prior to Altaris, Mr. Ellison was a member of the healthcare investment banking group at Lehman Brothers where he assisted clients in the execution of a number of mergers, acquisitions and financing transactions across the healthcare industry. Mr. Ellison holds a B.A. in Mathematics and Economics from Washington and Lee University. Our Board of Directors has concluded that Mr. Ellison’s company oversight experience and business experience make him well-qualified to serve on our Board of Directors.

Mr. O’Brien has served as our President and Chief Executive Officer, and as one of our directors, since he founded our Company in 1996. 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. Our Board of Directors has concluded that Mr. O’Brien’s extensive knowledge of our operations, finances, strategies and industry make him well-qualified to serve as our President and Chief Executive Officer, and on our Board of Directors.

Mr. Lee has served as one of our directors 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 our Board of Directors.

Mr. Jones has served as one of our directors since January 2008. Mr. Jones has served as the General Manager for Strategic Advisors Group, LLC since April 2001. From October 2010 to December 2017, Mr. Jones served as the Consulting Education Director for the National Association of Professional Surplus Lines Offices (“NAPSLO”), which is now the Wholesale & Specialty Insurance Association. Mr. Jones has over 40 years of experience in the specialty property and casualty insurance industry and has specific training as a wholesale broker, claims adjuster and underwriter. Mr. Jones holds a B.S. in Administration of Justice from Southern Illinois University and a M.Ed. from Central Michigan University. Our Board of Directors has concluded that Mr. Jones’s management experience and knowledge of the insurance industry make him well-qualified to serve on our Board of Directors.

Mr. Mayotte has served as one of our directors since July 2021. Mr. Mayotte served as the Chief Financial Officer for Oasis Outsourcing Holdings Inc. from July 2016 to December 2018, when it was acquired by

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 our Board of Directors.

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 our President and Chief Executive Officer and as one of our 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.”

Julie A. Baron has served as our Chief Financial Officer since April 2015 and as our Treasurer and Secretary since February 2020. 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).

Joy N. Edler has served as our Chief Operating Officer since January 2020. Prior to joining our Company, Ms. Edler served as the Vice President of Safety National Casualty Corp from January 2019 to January 2020, the Assistant Vice President of Safety National Casualty Corp from January 2016 to December 2018 and Director of Treaty Reinsurance at Safety National Casualty Corp from January 2014 to December 2015. Ms. Edler has experience as a senior-level treaty reinsurance underwriter and account executive responsible for developing, growing, and managing treaty reinsurance broker and client relationships, underwriting proportional and non-proportional programs, and promoting value-added client services. Ms. Edler also has a background in property and casualty insurance with an emphasis in workers’ compensation and other casualty. Ms. Edler holds a B.S. in Business Administration with an emphasis in Management and Human Resource Management from Columbia College.

Nicholas J. Vassallo has served as our Chief Accounting Officer since May 2020. 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).

Jill K. Johnson has served as our General Counsel since January 2015. Ms. Johnson has also served as the General Counsel and Vice President of Trean Corporation since April 2008, as the Secretary of S&C Claims Services, Inc. since September 2013 and as the Secretary of Benchmark Administrators, LLC since February 2016. Ms. Johnson holds a B.A. in Criminal Justice and Sociology from Gustavus Adolphus College and a J.D. from William Mitchell College of Law.

Matthew J. Spencer has served as our Chief Information 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, 2021, 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, 2020:

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, 2020 and December 31, 2019 is listed in the “Fiscal Year 2020 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 a discretionary annual cash incentive bonus as determined by our Board of Directors. The Compensation, Nominating and Corporate Governance Committee retains the right to award cash bonuses to our executive officers in its sole discretion and sound business judgment, if the committee determines that an executive officer made a significant contribution to the Company’s success. The Compensation, Nominating and Corporate Governance Committee has historically awarded cash incentive awards following each calendar year. The annual incentive bonuses actually awarded to each named executive officer are ultimately based on a discretionary performance evaluation conducted by our Compensation, Nominating and Corporate Governance Committee and Chief Executive Officer, in consultation with other executive officers. The determination involved an analysis of both (i) the Company’s overall performance, and (ii) the performance of the individual officer and his 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.

Equity Awards In Connection with the IPO. 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, received an equity award under the 2020 Plan in connection with the completion of the IPO. These awards consisted of an equal number of restricted stock units and stock options, with each award vesting in equal annual installments over three years. Ms. Baron received restricted stock units representing 14,050 shares of Common Stock and stock options representing 14,050 shares of Common Stock.

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, 2020 and December 31, 2019, are included in the “Fiscal Year 2020 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.

Severance Payments. In connection with the termination of his employment at the end of our fiscal year on December 31, 2020, Mr. Baker became entitled to receive cash severance in the amount of $700,000 that will be paid in equal bi-monthly amounts throughout the 2021 fiscal year.

The following table summarizes the number of outstanding equity awards held by each of our named executive officers as of December 31, 2020.

“Consulting Agreements”), relating to the engagement of Altaris to provide certain consulting and advisory services. The Consulting Agreements provide that we pay Altaris an annual fee of $1.0 million, payable quarterly in equal installments. We paid $1.0 million in each of 2018 and 2019 to Altaris for these services.

In connection with the IPO, we entered into a termination letter agreement with Altaris pursuant to which the parties agreed to terminate the ongoing consulting and advisory services and fees described above. Pursuant to the terms of such termination letter agreement, we agreed to pay Altaris an aggregate termination payment of $7.3 million, which amount equaled 1.0% of the enterprise value of us plus $1.5 million in accordance with the terms of the Consulting Agreements, paid upon completion of the IPO. Pursuant to the terms of such termination letter agreement, the consulting and advisory fees have terminated.

Section 16(a) of the Exchange Act requires our executive officers, directors and persons who beneficially own greater than 10% of a registered class of our equity securities to file reports of ownership and changes in ownership with the SEC. These persons are required by regulation to furnish us with copies of all Section 16(a) reports that they file. Based solely on our review of copies of these reports that we have received and on representations from all reporting persons who are our directors and executive officers, we believe that during 2020, all of our officers, directors and greater than 10% beneficial owners complied with all applicable Section 16(a) filing requirements except that one Form 4 was filed on October 20, 2020 with respect to 5,315 shares of Common Stock that were withheld by the Company in satisfaction of federal tax withholding obligations of Martin A. Ericson, our former Senior Vice President, in connection with the vesting of an award on July 16, 2020, as a result of a clerical oversight.

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.