Exhibit 99.1 Investor Presentation June 2022

Disclaimer This presentation of Trean Insurance Group, Inc. (the “Company”) contains forward-looking statements as that term is defined in the Private Securities Litigation Reform Act of 1995. Forward-looking statements include statements that are not historical or current facts. These statements may discuss the Company’s net income, cash flow, financial condition, impairments, expenditures, growth, strategies, plans, achievements, dividends, capital structure, organizational structure, market opportunities and general market and industry conditions. You can identify forward-looking statements by words such as “anticipate,” “estimate,” “expect,” “intend,” “plan,” “predict,” “project,” “believe,” “seek,” “outlook,” “future,” “will,” “would,” “should,” “could,” “may,” “can have,” “likely” and similar terms. Forward-looking statements are based on management’s current expectations and assumptions about future events. These statements are only predictions and are not guarantees of future performance. Forward-looking statements involve risks and uncertainties that could cause actual results to differ materially from those in the forward-looking statements, if the underlying assumptions prove to be incorrect or as the result of risks, uncertainties, and other factors, including the impact of the COVID-19 pandemic on the business and operations of the Company and our policyholders. Other factors that may cause such differences include the risks described in the Company’s filings with the U.S. Securities and Exchange Commission (the “SEC”), including its Quarterly Report on Form 10-Q for the quarter ended March 31, 2022. These forward-looking statements speak only as of the date of this presentation. Except as required by applicable securities laws, the Company disclaims any obligation to update or revise any forward-looking statement, whether as a result of new information, future developments, changes in assumptions or otherwise. You should not place undue reliance on the forward-looking statements contained in this presentation. All future written and oral forward-looking statements made in connection with this presentation attributable to the Company or persons acting on the Company’s behalf are expressly qualified in their entirety by the above paragraph. Filings with the SEC The Company’s filings with the SEC can be accessed through the “Investor Relations” link on the Company's website, www.trean.com. The Company’s filings with the SEC can also be accessed through the SEC's EDGAR Database at www.sec.gov (EDGAR CIK No. 0001801754). Non‐ GAAP Financial Measures Within this investor presentation we may present certain financial measures, including adjusted return on equity and adjusted net income, which are non‐ GAAP financial measures as defined in Regulation G pursuant to Section 401 of the Sarbanes‐ Oxley Act of 2002. If presented, a reconciliation of such non‐ GAAP financial measures to our most directly comparable GAAP financial measures will be included in the attached appendix. Management believes that these non‐ GAAP financial measures are important to the Company's investors, analysts and other interested parties who benefit from having an objective and consistent basis for comparison with other companies within our industry. Management further believes that these measures are more relevant than comparable GAAP financial measures in evaluating our financial performance. These measures should not be viewed as a substitute for those determined in accordance with GAAP. Reconciliation of these measures to their most comparable GAAP financial measures are included in the appendix to this presentation. They are also included in our most recent earnings release available in the “Investor Relations” section of our website at www.trean.com.

Company Overview Trean Insurance Group, Inc. An established, growth-oriented company providing products and services to the specialty insurance market. With a focus and expertise in underserved specialty casualty markets, Trean offers a multi-service model and produces a diverse set of revenue and earnings streams including: „Underwriting Income„Investment Income „Fronting Fees„Claims Fees „Reinsurance Brokerage„Managing General Agency (“MGA”) Income 2

Company Overview Underwriting Capacity with Issuing Carrier / ‘Fronting’ In-House Claims Reinsurance Brokerage Expertise in Specialty Services Management Services Insurance § Access to our A.M. Best “A” § Actively manage claims for our § Provide reinsurance placement, 2 rated carrier Owned MGA businesses and servicing and renewal services § In 1Q 2022, retained 40% of select Program Partners that gross earned premiums across § Licensed across multiple 1 underwrite workers’ 8 lines products in 49 states and D.C. compensation insurance 1 Represents the percentage of net earned premiums relative to gross earned premiums 2 Upgraded from A- (Excellent) to A (Excellent) in May 2019 3

Key Investment Highlights Multi-Service Value Proposition • Allows for unique positioning within the market • Creates better-than-industry results Proven and Sustainable Growth Strategy • Strong and disciplined program partner selection process • Disciplined risk management & well-managed balance sheet Entrepreneurial, Experienced Management Team • Expertise in Specialty Insurance, decades of industry experience and executive leadership • Supported by a board of directors with deep expertise and commitment to the Company Well-Positioned for Future Growth • Attractive embedded potential earnings • Consistently creating new opportunities 4

Multi-Service Value Proposition Unique Position in the Market Small Large Competitors Competitors Specialty risks that require ü ü Significant experience in workers’ compensation expert handling ~ and other specialty lines ü Broad licensing authority ü Licensed nationally across the U.S. and multiple product lines 1 “A” rating by A.M. Best ü ü Infrastructure and capability ü ü Specialty expertise in underwriting, loss control, to service longer-tailed risks ~ claims, and customer knowledge Focus on small- to mid-sized ü ü programs Target <$30 million at inception ü Focus on small accounts ü ~$14,000 average workers’ compensation 2 premium per policy Ability to partner with ü ü entrepreneurial partners Multi-Service Value Proposition 1 Upgraded from A- (Excellent) to A (Excellent) in May 2019 2 As of March 31, 2022 5

Multi-Service Value Proposition Better-Than-Industry Results Superior In-House Claims Management Personal, high-touch claims management approach to reduce chance of lengthy and costly litigation Provide an injured Fully settle the claim Commitment to Average 93 open claims 1 employee high-quality and obtain a full and delivering the best per claims adjuster medical care as quickly complete release claims process More than 20% lower than the as possible industry average of over 116 At the earliest opportunity when Exemplified by expertise of our 2 open claims per claims adjuster an injured employee has healed claims administration Reduce pain, accelerate department, who average 16 healing, and lead to faster and 1 years of industry experience more complete recovery 1 As of December 31, 2021 2 Per 2020 Workers’ Compensation Benchmarking Study by Rising Medical Solutions 6

Multi-Service Value Proposition Better-Than-Industry Results Superior In-House Claims Management Better Claims Outcomes Quicker Claim Inventory Reduction Faster Claim Closure Average medical costs incurred per claim Percentage of indemnity claims closed in 5-year paid to ultimate losses vs 2 3 vs California average the next year vs California average U.S. industry average Trean California Trean California Trean workers' compensation California workers' compensation California workers' compensation U.S. workers' compensation industry 1 $30.1k 87% 67% 70% 1 $10.3k 33% 2021 2021 2021 1 WCIRB, as of December 31, 2021 2 Percentage of claims per accident year closed by the next calendar year; as of year end 3 Per S&P Global, trailing four year average of 60 month paid to ultimate loss ratios as of 12/31/2021, Statutory data 7

Proven and Sustainable Growth Strategy Impressive and Steady Gross Written Premium Growth $649m $634m $484m $411m $357m $322m $236m $145m 2015 2016 2017 2018 2019 2020 2021 1Q 2022 TTM 2015 2017 2020 2021 2018 • Sold an equity • Acquired American • Acquired remainder of • Acquired Western • Acquired 45% of stake to Altaris to Liberty Insurance Compstar Integrated Care Compstar take advantage of Company (“ALIC”), • Acquired 7710 Insurance • Added 2 Program • Acquired 100% of growth a former Program Company Partners Westcap opportunities Partner • Acquired LCTA Risk Services, Inc. • Added 9 Program Partners Source: Company filings 8

Proven and Sustainable Growth Strategy Strong and Disciplined Program Partner Selection Process Our reinsurance Referrals from New opportunities brokerage existing Program services Partners Carefully Selected Program Partners Stringent Selection Criteria Collect and analyze data relating to the organization’s operating, Pre-screening underwriting, financial and biographical information Top ~10% of opportunities make it through pre-screening and due diligence process Detailed Due Diligence Partners Retain Meaningful Risk Establish stringent underwriting and collateral requirements upfront Carefully Aligned Disciplined Ongoing Controls Program Design Regular underwriting, claims, and accounting audits Ongoing 1 Monitoring Average Program Partner Relationship of ~8 Years and Controls 1 Excluding Program Partners added in the prior two years 9

Proven and Sustainable Growth Strategy Strong and Disciplined Program Partner Selection Process Trean’s Target Program Partners Small- to mid-sized Ability to create a Track record of Proven ability to manage books of business competitive advantage underwriting success the program Less than $30 million of annual By operating in markets where With credible data to support Pursuant to agreed-upon gross premiums at the inception distinctive expertise, multi- historical results (i.e., loss ratios, underwriting and claims of the relationship service offering, and market expense ratios, etc.) guidelines relationships can be leveraged Capacity to assume Collaborative, Willingness and ability to meaningful risk entrepreneurial control the structuring participation in the management team and placement of program reinsurance Partnership Oriented 10

Proven and Sustainable Growth Strategy Disciplined Risk Management and Well-Managed Balance Sheet Comprehensive Reinsurance Prudent Financial and Accurate Reserving Program Operating Leverage 1 o Favorable development of our initial o Workers’ compensation losses o $416 million shareholders’ equity reserves for each accident year reinsured for 500-year return period 1 o 7% debt / total capital since 2012, with $45.7 million of probable maximum loss, with varying o 2021 NWP / average total capital aggregate favorable development co-participations through the first $15 2 operating leverage of 1.3x 1 since 2014 million Systematic monitoring and Diversified and Conservative Active collateral management control of Program Partners Investment Portfolio 1 o Nearly $2.4 billion premiums ceded o Highly disciplined process o Weighted average rating of “AA” to reinsurers since 2007, with no 1 o Regular underwriting, claims, and o Weighted average duration of 4.3 years 1 unpaid reinsurance recoverables accounting audits 1 o Tax-equivalent book yield of 2.41% o Reinsurers are fully collateralized, or rated “A-” or better o Review collateral accounts regularly and secured with quarterly and annual adjustments 1 As of March 31, 2022 2 Statutory data 11

Entrepreneurial, Experienced Management Team Decades of Industry Experience Prior Professional Experience Years Experience o General Partner, Executive Vice President and director of E.W. Blanch Company o Director of the Health Care Insurance Facility, First Dakota Indemnity Company ANDREW O’BRIEN 30+ CHIEF EXECUTIVE OFFICER years and SAFE, Inc., a holding company for an accident and health Insurer o Joined Trean in 2007 as the Controller for Benchmark and has held the role of JULIE BARON Chief Financial Officer, as well as Treasurer and Secretary. 30+ PRESIDENT AND CHIEF years OPERATING OFFICER o Controller for a mortgage broker and title company, and an auditor at a Minneapolis-based CPA firm. NICK VASSALLO 25+ o Joined Trean in 2020 as the Chief Accounting Officer and Senior Vice President CHIEF FINANCIAL OFFICER years o 25+ years of public company experience ELISABETH ROSANDICH o Joined Trean in 2019 after almost 9 years at Berkley Risk Administrators in 15+ CHIEF UNDERWRITING positions of Underwriting Manager and AVP of Program Services. years OFFICER o Prior reinsurance and claims experience at Aon Benfield o Practicing law for 28 years, always in insurance and reinsurance. I have been PATTY RYAN 25+ working for insurance companies since 2006. CHIEF LEGAL OFFICER years o Has served Trean’s General Counsel and Corporate Secretary since 2021 MATTHEW SPENCER CHIEF INFORMATION AND 20+ o Vice President of Business Technology at Trean SECURITY OFFICER years o Previously Vice President of Operations at FARA and Senior Vice President of DEAN CLIFTON 30+ Workers Compensation Claims with Old Republic Construction Program Group. SVP CLAIMS years Joined Trean in 2018 as Vice President of Claims 12

Well-Positioned for Future Growth Attractive Embedded Earnings Illustrative Income Statement Impact of Increasing Retention Summary of Impact 0% 25% 50% As retention increases… Retention Retention Retention Direct Premium Direct Premium $1,000 $1,000 $1,000 Net Premium Net Premium - 250 500 Ceding Commissions Ceding Commission 300 225 150 U/W Expenses Underwriting Expenses (260) (260) (260) Loss Ratio Losses - (150) (300) Underwriting Profit $40 $65 $90 Underwriting Profit Expenses (40) 35 110 1 Expense Ratio NM 14.0% 22.0% Increased underwriting participation drives increased profitability; expense ratio increase is a mechanical output from this intentional strategy 1 Expense ratio is calculated as follows: (Underwriting Expenses less Ceding Commission) ÷ Net Premium 13

Well-Positioned for Future Growth Attractive Embedded Potential Earnings 1 Underwriting Participation (Retention) Net Unearned Premium $102m 41% $91m 35% $50m 25% 22% 20% $24m $23m 2018 2019 2020 2021 As of 1Q 2018 2019 2020 2021 1Q YTD 2022 2022 Purposeful increase in underwriting participation creates significant deferred potential future earnings Source: Company filings 1 Represents the percentage of net earned premiums relative to gross earned premiums 14

Well-Positioned for Future Growth Consistently Creating New Opportunities Gross written premiums Selectively Adding Growing in New Partners Existing Markets $649m $634m • Target large markets, • 9 Program Partners added with significant room in 2020, 2 in 2021, and 5 to grow additional YTD in 2022 • 27% Gross Written • Ensure new Partners Premium CAGR $484m share business philosophy since 2015 $411m $357m Opportunistically Harnessing Growing $322m Growing Through Capital Base M&A $236m • Eight MGA acquisitions • Increase net retention since 2013 • Drive growth in chosen • Created Benchmark markets and segments $145m Specialty Insurance Company in 2021 2015 2016 2017 2018 2019 2020 2021 1Q'22 TTM Source: Company filings 1 GWP CAGR includes Program Partners and Owned MGAs for the period ended March 31, 2022 15