#1HERITAGE INSURANCE Investor Presentation (NYSE: HRTG) March 2022#2SAFE HARBOR Statements in this presentation that are not historical facts are forward-looking statements that are subject to certain risks and uncertainties that could cause actual events and results to differ materially from those discussed herein. Without limiting the generality of the foregoing, words such as "may" "will," "expect," "believe," "anticipate," "approximate," "plan," "intend," "could," "would," "estimate," or similar expressions are intended to identify forward-looking statements. Forward looking statements include, but are not limited to, statements about the Company's expectations with regard to net investment income, underwriting margins and capital to support future premium growth and expansion initiatives. These statements are not guarantees of future performance and involve risks, uncertainties and assumptions that could cause the Company's actual results to differ materially from those expressed or implied by such forward-looking statements. Such risks and uncertainties include, among other things, risks related to the possibility that actual losses may exceed reserves; the concentration of the Company's business in coastal states, which could be impacted by hurricane losses or other significant weather-related events such as northeastern winter storms; the Company's exposure to catastrophic weather events; increased costs of reinsurance, non-availability of reinsurance, and non-collectability of reinsurance; the Company's failure to effectively manage its growth and integrate acquired companies; increased competition, competitive pressures, and market conditions; the Company's failure to accurately price the risks it underwrites; the inherent uncertainty of the Company's models and reliance on such models as a tool to evaluate risk; the failure of the Company's claims department to effectively manage or remediate claims; low renewal rates and failure of such renewals to meet the Company's expectations; the Company's failure to execute its diversification strategy; failure of the Company's information technology systems and unsuccessful development and implementation of new technologies; a lack of redundancy in the Company's operations; the Company's failure to attract and retain qualified employees and independent agents or loss of key personnel; the Company's inability to generate investment income; the Company's inability to maintain its financial stability rating; effects of emerging claim and coverage issues relating to legal, judicial, environmental and social conditions; the failure of the Company's risk mitigation strategies or loss limitation methods; changes in regulations and the Company's failure to meet increased regulatory requirements; and other matters described from time to time by the Company in its filings with the Securities and Exchange Commission, including, but not limited to, those set forth in its Annual Report on Form 10-K for the year ended December 31, 2020 and subsequent Quarterly Reports on Form 10-Q (or such other reports that may be filed with the SEC). The Company undertakes no obligations to update, change or revise any forward- looking statement, whether as a result of new information, additional or subsequent developments or otherwise, except as required by law. Non-GAAP Financial Information: This presentation includes financial measures that are not presented in accordance with generally accepted accounting principles in the U.S. (GAAP). A reconciliation of these non-GAAP financial measures to the most directly comparable GAAP financial measure can be found in the Appendix to this presentation on slide 25. Note: This presentation also contains information regarding securities analyst consensus and other financial professionals' estimates of certain financial items for Heritage and other industry participants derived from reports of FactSet Research Systems ("FactSet"). These estimates are projections made by securities analysts and other financial professionals who cover Heritage and other industry participants. Any opinions, forecasts, estimates, projections or predictions regarding Heritage's performance made by such third parties (and, therefore, such estimates) are theirs alone and do not represent the opinions, forecasts, estimates, projections or predictions of Heritage or its management. By providing these estimates, Heritage does not imply its adoption of, endorsement of or concurrence with such information, conclusions or recommendations. Heritage assumes no liability for the accuracy of such estimates and undertakes no liability to update or revise such estimates based on new information or otherwise. March 2022 Investor Presentation 2 H#3Company snapshot.. Timeline of events........ Management team.. Corporate structure. Book of business.......... In-force metrics........... Distribution........ Reinsurance program. Investments........... Value proposition........ TABLE OF CONTENTS COMPANY OVERVIEW INVESTMENT CONSIDERATIONS Strategic InsurTech partnership...... Underwriting performance, capital management and underwriting leverage........ Diversification strategy..... Book value per share growth, ROEs and valuation........ Investor relations contact details............ Note 1: all market data as of the close on 3/7/2022 unless otherwise noted Note 2: all non-market data as of 12/31/2021 unless otherwise noted March 2022 Investor Presentation 7 569 8 9 10 11 12 13 15 16 17-19 20 21 22 H 3#4Company overview Heritage Insurance H#5COMPANY SNAPSHOT What we do: Heritage Insurance Holdings, Inc. is a super-regional property and casualty insurance holding company with roughly $1.2 billion of personal/commercial residential and commercial general liability premium across its multi- state footprint. QUICK FACTS Personal residential insurer in 16 US states & licensed in 1 additional state 19th largest homeowners' insurer nationwide (as of 12/31/2020) Commercial residential insurer in FL, NY & NJ 4th largest non-liability commercial multiple peril (CMP) insurer in FL (as of 12/31/2020) Vertically integrated structure with in-house underwriting, actuarial, customer service, claims processing and adjusting functions (3rd parties used as needed) 648 employees (637 full-time) ➤ Founded in 2012, followed by IPO in 2014 Headquartered in Tampa, FL NYSE: HRTG MARKET/FINANCIAL DATA Market Cap/Stock Price: $156 million/$5.59 Annual Dividend/Yield Per Share: $0.24/4.3% Remaining share repurchase authorization: $25.0 million. Total Equity/BVPS: $343.1 million/$12.82 Total Assets: $2.0 billion In-Force Premiums: $1.2 billion Financial Strength Ratings: Demotech: HPCIC (A), NBIC (A), ZIC (A Prime) Kroll: HPCIC (BBB+), NBIC (A-), ZIC (BBB+) Investment grade issuer rating (Kroll: "BBB-") March 2022 Investor Presentation LO 5 H#6THE HERITAGE STORY Founded in 2012, Heritage has quickly grown into a leading coastal US P&C insurer. 2012 Company inception Started writing voluntary personal residential (PRES) business in FL Participated in first personal residential assumption from FL Citizens 2015 Initiated quarterly cash dividend 2017 Began writing PRES in GA and AL Sawgrass Mutual policy assumption ➤ Acquired NBIC, a coastal HO insurer in NY, NJ, CT, RI & MA -2019 Began writing PRES in VA Began writing CRES in NJ (first CRES expansion outside FL) Expanded product offering in Hawaii 2014 HRTG IPO (NYSE): $11/share Sunshine State policy assumption Launched commercial residential (CRES) division and participated in first commercial residential assumption from FL Citizens March 2022 Investor Presentation 2016- ➤ Began writing PRES in NC & SC, beginning of multi-state expansion Acquired Zephyr, a wind-only HO insurer in HI Launched GL insurance in FL Commenced Nat Gen partnership ➤ AoB begins to meaningfully impact results Final year Heritage participated in Citizens assumptions 6 2018- Received KBRA financial strength and investment grade issuer ratings ➤ CAN expansion to non-FL states GEICO relationship expands ➤ Commenced Safeco (Liberty Mutual) partnership ➤ Eliminated majority of convertible debt used to acquire NBIC 2020- Surpassed $1B of premiums in- force ➤ Began writing PRES in CA, DE, MD and MS ➤ Commenced partnership with The Hartford H#7EXPERIENCED MANAGEMENT TEAM Ernie Garateix: Chief Executive Officer Has been in his current role since 2020, prior to which he served as Chief Operating Officer since 2014. Before that, he served as Executive Vice President since the company's 2012 founding. Prior to Heritage, Mr. Garateix served as Vice President of Operations at American Integrity Insurance Group. Before that, Mr. Garateix was Associate Vice President of IT at FCCI Insurance Group. Kirk Lusk: Chief Financial Officer Has been in his current role since 2018. Joined Heritage in 2017 via the acquisition of NBIC Holdings, Inc., where Mr. Lusk was also Chief Financial Officer. Before that, Mr. Lusk was International Chief Financial Officer of Aetna, Inc., Chief Financial Officer of Alea Group Holdings Bermuda Ltd. and Chief Financial Officer of GE ERC Global Casualty and GE Capital Auto Warranty Services. Tim Moura: President, NBIC Has been in his current role since 2017, prior to which he served as SVP of Marketing, Agency, and Client Services since 2014. Prior to NBIC, Mr. Moura served as Vice President of Business Development and Commercial Lines for Tower Group Companies. was Vice Before that, Mr. Moura President, Underwriting and Product Management, Personal Lines, at OneBeacon Insurance Group. March 2022 Investor Presentation Tim Johns: President, Zephyr Has been in his current role since 2018. Prior to Zephyr, Mr. Johns was Chief Consumer Officer at the Hawaii Medical Service Association, the largest health insurer in Hawaii. Before that, Mr. Johns held multiple executive leadership roles within private, public and non-profit enterprises in Hawaii. 7 Randy Jones: President, Commercial Division Has been in his current role since 2014. Prior to Heritage, Mr. Jones was SVP of American Strategic Insurance's (ASI) commercial division. Before that, Mr. Jones served in management at other insurance enterprises. Mr. Jones holds the American Risk Manager (ARM) and Certified Property Insurance Adviser (CPIA) designations. H#8VERTICALLY INTEGRATED STRUCTURE Unique, vertically integrated structure reduces our reliance on third parties, benefiting our loss, LAE and operating expenses, while also serving as a hedge during catastrophe years. ➤ Vertically integrated structure reduces our earnings volatility, supporting P/E-based valuation for HRTG. MGA structure allows us to meet holding company capital needs (e.g., debt servicing, share repurchases, M&A, etc.) Risk bearing entity (AL, CA, GA, FL, MS, NC, SC) Heritage Property & Casualty Insurance Company (HPCIC) NBIC Holdings, Inc ORGANIZATIONAL STRUCTURE Heritage Insurance Holdings, Inc. (NYSE: HRTG) Zephyr Acquisition Company Heritage MGA, LLC Heritage Insurance Claims, LLC Contractors' Alliance Network (CAN) Osprey Re Ltd. Skye Lane Properties, LLC NBIC Financial Holdings, Inc. NBIC Service Company Westwind Underwriters, Inc. HI Holdings, Inc. Provides NBIC with Narragansett Bay underwriting, personnel Insurance Company and other services (NBIC) Risk bearing entity (CA, CT, DE, MA, MD, NY, NJ, RI, VA) March 2022 Investor Presentation Zephyr Insurance Company, Inc. (ZIC) Provides HPCIC & ZIC with underwriting, personnel and other services Mitigation and construction Captive reinsurer division, serves as a hedge in catastrophe years Risk bearing entity (HI) 8 Subsidiary that owns Heritage's corporate headquarters H#9BOOK OF BUSINESS Heritage has $1.2 billion of premiums in-force across three statutory insurance entities (Heritage/NBIC/Zephyr) and primarily writes personal residential (PRES) insurance. Heritage also writes commercial residential (CRES) insurance and a small amount of commercial general liability (CGL) insurance. Heritage is actively writing in sixteen states, but has licenses in seventeen. GEOGRAPHIC FOOTPRINT TOTAL INSURED VALUE (PROPERTY) GROSS PREMIUMS-IN-FORCE Other*, 13% NC, 3% Other*, 17% NC, 2% FL, 27% HI, 10% HI, 5% MA, 6% NJ, 7% = actively writing licensed Powered by Bing © GeoNames, MSFT, Navteq 3 Statutory Insurance Entities: March 2022 Investor Presentation MA, 8% NY, 25% NJ, 10% NY, 18% FL, 48% *Other includes AL, CA, CT, DE, GA, MD, MS, RI, SC, & VA PRES = personal residential ⚫CRES = commercial residential • CGL = commercial general liability ⚫ TIV = total insured value AL, CA, FL, GA, MS, NC, SC CA, CT, DE, MA, MD, PA, NJ, NY, RI, VA HI H→> H HERITAGE® INSURANCE Narragansett Bay Insurance ZEPHYR INSURANCE COMPANY, INC. 6 H#10IN-FORCE METRICS Florida property insurance only accounts for 27% of Heritage's property total insured value (TIV), but reflects 48% of premiums in-force - the $540 Florida personal residential (PRES) insurance average premium per $100,000 of TIV is more than double the $210 non-Florida average (Florida's more expensive policies reflect its higher hurricane and litigation risk), while the $409,263 Florida PRES average insured value is well below the $813,594 average for non-Florida states (property values in Florida trail those in Heritage's northeast US states). Premium/$100k TIV 1,200 1,000 800 $1,050 IN-FORCE METRICS ($ in millions) Premiums In-Force YE2015 YE2016 YE2017 YE2018 PRES $478 $516 $850 $837 YE2019 $861 YE2020 YE2021 $969 $1,052 CRES $113 $119 $90 $83 $73 $104 $110 CGL $0 $1 $2 $4 $6 $9 $11 Total $592 $635 $942 $924 $941 $1,082 $1,172 Policies In-Force 600 $540 $537 YE2015 400 $452 $425 $259 $402 $210 PRES 253,726 CRES 3,405 CGL Total 257,131 YE2016 318,824 3,625 852 323,301 YE2017 518,957 YE2018 YE2019 YE2020 YE2021 508,424 522,442 568,068 556,507 3,100 2,973 2,533 3,074 2,745 2,393 524,450 4,289 6,970 515,686 531,945 9,904 581,046 12,064 571,316 200 0 FL PRES Non-FL PRES FL PRES TC FL PRES ex-TC FL CRES Non-FL CRES FL CRES TC FL CRES ex-TC FL PRES TIV/PIF $409,263 FL PRES ex-TC $416,329 Non-FL PRES FL PRES TC $813,594 $372,655 TIV = total insured value • PIF = policies in-force • PRES = personal residential •CRES = commercial residential • TC = Tri-County (FL) FL CRES $9,706,149 Non-FL CRES $7,146,416 FL CRES TC FL CRES ex-TC $12,022,485 $9,346,289 PRES CRES Total Total Insured Value (Property) YE2015 YE2016 YE2017 YE2018 YE2019 YE2020 YE2021 $72,102 $109,888 $289,974 $296,432 $316,075 $353,780 $371,734 $22,764 $26,367 $22,832 $23,038 $20,958 $27,851 $26,241 $94,866 $136,256 $312,806 $319,470 $337,033 $381,632 $397,975 March 2022 Investor Presentation 10 H#11. Overview HPCIC DISTRIBUTION Robust organic growth engine via independent agency relationships and auto carrier partnerships across our multi-state platform . • . Over 2,700 actively writing retail independent agents 25% of voluntary premium is written by agents affiliated with eight large agency networks that have master agency agreements with HPCIC CRES policies are written through roughly 400 independent agents Relationships with multiple auto carriers Roughly 500 retail independent agents representing approximately 800 agency locations 8 wholesale relationships that have access to 1,500 retail locations Relationships with 70 actively writing independent agencies 51% of voluntary premium is written by agents affiliated with three large agency networks . NBIC . Zephyr . March 2022 Investor Presentation 11 H#12CATASTROPHE REINSURANCE PROGRAM Heritage has a conservative 2021-2022 catastrophe reinsurance program, protecting the Company against hurricanes and severe weather events and reducing earnings volatility. Substantial severity and frequency protection. First event reinsurance tower exhaustion point of $1.4 billion and total limit of $2.5 billion in the southeast. Reinstatement premiums for all layers with a reinstatement available have been prepaid. Within the reinsurance tower, we have no co-participation above our regional retentions. First event retentions in the southeast and Hawaii of $32.0 million, accounting for 9.3% of 4Q2021 GAAP equity (pre-tax). First event retention in the northeast of $20.7 million, accounting for 6.0% of 4Q2021 GAAP equity (pre-tax). Total cost to Heritage of $312 million, accounting for 27% of 4Q2021 premiums in-force. Heritage's third-party reinsurers are rated "A-" or higher by A.M. Best or S&P or are fully collateralized. March 2022 Investor Presentation 12 H#13INVESTMENT PORTFOLIO Heritage has a very conservative investment portfolio, consisting predominantly of low duration, fixed income securities. As of 4Q2021, duration was 3.9 years, in line with 3Q21 and 0.3 years above 4Q2020's 3.6 years. INVESTMENT PORTFOLIO BREAKDOWN (4Q2021) NET INVESTMENT INCOME PERFORMANCE Other, 4% US government, 11% $800 3.0% $700 Industrial & misc. bonds, 29% Munis, 15% Investments ($ in millions) 2.6% 2.4% 2.5% $600 2.0% 1.8% 1.9% 2.1 2.0% $500 1.6% $400 1.4% 1.5% $300 0.9% 1.0% $200 0.5% Special revenue $100 bonds, 42% $0 $136.2 $331.2 $400.1 $603.0 $567.0 $528.6 $595.2 $589.0 $694.7 2013 2014 2017 0.0% 2018 2019 2020 2021 March 2022 Investor Presentation 13 2015 2016 Investments (left axis) Net investment income (right axis) H Net investment income yield#14Investment considerations Heritage Insurance H#15Compelling financial metrics Business model designed to reduce earnings volatility Growth & underwriting outlooks improving Prudent capital management Management and BoD have significant skin in the game . VALUE PROPOSITION Currently trading at significant discount to peers, despite attractive relative ROE and income metrics • Consistent track record of book value growth Vertically integrated structure provides a hedge in catastrophe years, reducing loss retention and further reducing earnings volatility, supporting use of P/E-based valuation for HRTG • Solid reinsurance program, including lowest reinsurance retention in FL peer group as a % of equity; protects against hurricanes and other severe events, reducing earnings volatility • Organic premium growth, fueled by relationships with independent agents and auto carriers Diversification initiatives and recent re-underwriting and de-risking efforts should benefit underwriting margins Commercial residential business serves as an AoB-hedge in Florida and provides us with additional growth opportunities Investment grade debt rating provides easy access to capital, allowing nimble response to market opportunities as they arise Below-peer operating leverage = ample capital to fuel our growth • Track record of capital return via share repurchases and regular dividend . Successful M&A execution provides synergies and access to new markets Significant insider ownership aligns management's and BoD's interests with shareholders Total insider ownership = 9% of outstanding shares March 2022 Investor Presentation 15 H#16STRATEGIC INSURTECH PARTNERSHIP Entered into a strategic partnership with Slide, a startup InsurTech P&C carrier, providing Heritage with enhanced technological capabilities and allowing for participation in the InsurTech sector's upside. Partnership provides Heritage with the opportunity to: Leverage Slide's InsurTech capabilities to improve underwriting and rating decisions. Further capitalize on strong agency relationships by generating commission income on policies that don't meet Heritage's underwriting criteria (e.g., due to geographic concentration). Participate in the InsurTech sector without potentially significant capital requirements to develop similar capabilities internally. Based on current publicly traded InsurTech valuations, potential to generate a meaningful capital gain, which, if realized, could provide additional funds for share buybacks or debt retirement. Terms of the partnership Heritage will receive: Approximately 6% equity stake in Slide, an InsurTech P&C carrier with an estimated $250 million post-money valuation, and warrants allowing it to purchase an additional equity interest at Slide's pre-money valuation. Slide will be accounted for as an equity investment. Perpetual, royalty free license to certain aspects of Slide's software. Heritage will: Transfer ownership (subject to regulatory approval) of Pawtucket (Heritage will retain Pawtucket's surplus), a dormant P&C carrier licensed in Rhode Island. Transfer ownership of First Access Insurance Group, a Florida-licensed MGA with minimal earnings. Provide access to historical claims and underwriting data. March 2022 Investor Presentation 16 H#17PREMIUM GROWTH Heritage has experienced significant premium growth since inception, most recently stemming from organic growth, while earlier growth stemmed from Citizens depopulation transactions and M&A. Heritage's premium growth is unprecedented, reaching over $1 billion of premiums in-force 8 years after the company's founding. The modest premium decline in 2018 and low premium growth in 2019 stemmed from Tri-County FL exposure reduction efforts. $1,200 $1,000 $800 $600 $400 $461.3 IN-FORCE PREMIUM $1,172.1 59.6 $1,082.3 54.4 $942.4 55.4 $923.7 53.5 $940.6 53.5 331.5 337.2 356.3 $635.3 $591.5 58.1 461.3 398.6 629.2 651.2 591.5 577.2 555.5 533.0 530.8 $200.1 461.3 $200 $51.6 200.1 51.6 $0 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 HPCIC NBIC Zephyr H March 2022 Investor Presentation 17#18UNDERWRITING PERFORMANCE (CONTINUED) Heritage's underwriting operation has generally produced solid combined ratios. SOLID UNDERWRITING MARGINS 120% 100% 107.0% 104.6% 94.1% 96.5% 92.8% 90.4% 38.5% 34.7% 80% 72.9% 71.4% 39.4% 34.8% 41.0% 38.1% 65.0% 60% 32.4% 31.3% 27.5% 40% 68.5% 69.9% 58.0% 57.1% 53.1% 52.3% 20% 40.5% 40.1% 37.5% 0% 2013 2014 Citizens takeouts benefit HRTG's margins March 2022 Investor Presentation 2015 2016 Tornadoes, 2017 Hurricane Hurricanes Irma & AoB Hermine & Matthew, AOB ■Loss ratio (left axis) 18 2018 Hurricanes Lane, Florence & Michael, AoB 2019 Southeast hail and wind storms, Hurricane Dorian Expense ratio (left axis) 2020 Hurricanes Isaias, Sally and Eta, Southeast hail, tornado and wind storms 2021 Convective storms and hurricanes Elsa, Fred, Henri and Ida. H#19CAPITAL MANAGEMENT & OPERATING LEVERAGE Heritage has been a responsible steward of shareholder capital and currently has $25.0 million remaining on its share repurchase authorization. Since 2015, the Company has returned $125.5 million to shareholders through common share repurchases and dividends. Heritage's ratio of trailing-twelve-month (TTM) net premiums written to 4Q2021 equity is only 1.8x, which is indicative of its conservative balance sheet. Looking ahead, Heritage has adequate capital to fuel its premium growth and multi-state expansion initiatives. DISCIPLINED CAPITAL MANAGEMENT $ in millions March 2022 Investor Presentation $70 $60 $50 35% $40 $32.6 $28.1 $30 18% 27% 23% 22% 40% 35% 30% 26% 25% 20% $23.3 15% $20 25.6 $16.8 21.6 $14.9 10% 16.1 $8.4 10.0 $10 8.2 5% 2.0 $1.6 7.0 6.5 7.1 6.8 6.7 $0 0% 2015 2016 2017 2018 2019 2020 2021 I Dividends Share repurchases Debt-to-capital ratio (right axis) Note: Debt-to-capital calculated as debt principal divided by the sum of debt principal and stockholders' equity 19 H#20DIVERSIFICATION STRATEGY UNDERWAY % OF CONSOLIDATED PROPERTY TOTAL INSURED VALUE (TIV) IN FLORIDA 100.0% 100.0% 100.0% 100.0% 100% 90% 80% 34.0% Zephyr acquisition Heritage has been reducing its exposure to Florida's Tri-County region and diversifying to new states, resulting in a better spread of risk, better claims trends and lower reinsurance costs. 70% 58.9% 70.6% 57.1% 67.6% 60% 50% 25.7% 41.3% NBIC acquisition 40% 15.4% 30% 32.1% 31.6% 30.1% 31.3% 26.9% 20% 41.1% 11.5% 40.3% 21.7% 32.4% 23.3% 23.7% 25.8% 10% 27.5% 22.8% 17.8% 3.8% 2.9% 0% 6.6% 2.0% 5.5% 1.9% 4.3% 3.5% 1.1% 3:0% 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 March 2022 Investor Presentation Personal Residential: Tri-County, FL Commercial Residential: Tri-County, FL 20 Other FL H#21$12 $10 $8.56 $8 $7.20 $6 $4 $3.38 $2 March 2022 Investor Presentation $3.38 SOLID BOOK VALUE PER SHARE GROWTH Since inception, Heritage has provided investors with solid book value per share growth. Including cumulative dividends declared, Heritage's book value per share compound annual growth rate (CAGR) is 17% since the Company's 2012 inception. $18 $16 $14 SOLID GROWTH IN BOOK VALUE AND CUMULATIVE DIVIDENDS PER SHARE CAGR - since inception: 17% • 2015: 3% • 2017: -2% $17.19 $16.67 $1.25 $15.20 $1.01 $15.20 $0.53 $0.77 $14.31 $12.70 $1.49 $11.76 $0.29 $7.20 $0 2012 2013 2014 $8.56 $11.71 2015 Book Value Per Share 2016 21 $12.41 $0.05 $14.67 $14.43 2017 2018 Cumulative Dividends Per Share 2019 $15.66 $15.94 2020 2021 $12.82 H#22ADDITIONAL INFORMATION [email protected] Website: investors.heritagepci.com H HERITAGE 11 INSURANCE