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Investor Presentation (NYSE: HRTG) September 2019 SAFE HARBOR Statements in this presentation that are not historical facts are forwardlooking statements that are subject to certain risks and uncertainties that could cause actual events and


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SLIDE 1

Investor Presentation

(NYSE: HRTG) September 2019

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SLIDE 2

SAFE 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 H 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, 2017 and subsequent Quarterly Reports

  • n 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.

2 September 2019 Investor Presentation

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TABLE OF CONTENTS

Company snapshot………………………………………………………………………………………………………………………………………………………………………. Timeline of events..……………………………………………………………………………………………………………………..………………………………………………. Management team.……………………………………………………………………………………………………………………………………………………………………… Corporate structure..………………………………………………………………………………………………………………………………………………….……………...... Book of business……………………………………………………………………………………………………………………………………..…………………………………… In‐force metrics……………………………………………………………………………………………………………………………………………………………………………. Distribution………………………………………………………………………………………………………………………………………………………………………….......... Reinsurance program…………………………………………………………………………………………………………………………………………………………………… Investments……………………………………………………………………………………………………………………………………………………………………….……..….

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INVESTMENT CONSIDERATIONS COMPANY OVERVIEW

Note 1: all market data as of the close on 9/20/2019 unless otherwise noted Note 2: all non‐market data as of 6/30/2019 unless otherwise noted September 2019 Investor Presentation

Value proposition…………………………………………………………………………………………………………………………………………………………………......... Underwriting performance, capital management and underwriting leverage…………………………….………………………………………………... Diversification strategy…………………………....…………………………………………………………………………………………………………………………...…….. Book value per share growth, ROEs and valuation……………………………………………………………………………………………………………………….. Appendix: Reconciliation of GAAP and non‐GAAP measures………………………………………………………………………………………………….…….. Investor relations contact details………………..……………………………………………………………………………………………………..………………….……… 5 6 7 8 9 10 11 12‐13 14 16 17‐19 20‐21 22‐24 25 26

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Company overview

Heritage Insurance

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COMPANY SNAPSHOT

  • Active personal residential insurer in 12 coastal US

states & licensed in 4 additional states

  • 6th

largest homeowners insurer in FL and 22nd nationwide (as of 12/31/2018)

  • Active commercial residential insurer in FL & NJ
  • 2nd largest admitted commercial residential insurer in FL

and 7th largest commercial multiple peril (CMP) insurer in the state (as of 12/31/2018)

  • Vertically

integrated structure with in‐house underwriting, actuarial, customer service, claims processing and adjusting functions (3rd parties used as needed)

  • 453 employees (447 full‐time)
  • Founded in 2012, followed by IPO in 2014
  • Headquartered in Clearwater, FL

What we do: Heritage Insurance Holdings, Inc. is a super‐regional property and casualty insurance holding company with over $900 million of gross personal and commercial residential premium across it’s multi‐state footprint.

  • NYSE: HRTG
  • Market Cap/Stock Price: $438 million/$14.67
  • Annual Dividend/Yield Per Share: $0.24/1.6%
  • Remaining share repurchase authorization: $42.7 million
  • Total Equity/BVPS: $438.9 million/$14.99
  • Total Assets: $1.9 billion
  • In‐Force Gross Premiums: $922.5 million
  • Financial Strength Ratings:
  • Demotech: HPCIC (A), NBIC (A), ZIC (A Prime)
  • Kroll: HPCIC (BBB+), NBIC (A‐), ZIC (BBB+)
  • Investment grade issuer rating (Kroll: “BBB‐”)

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QUICK FACTS MARKET/FINANCIAL DATA

September 2019 Investor Presentation

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THE HERITAGE STORY

Founded in 2012, Heritage has quickly grown into a leading coastal US P&C insurer.

6

2012

  • Company inception
  • Started writing

voluntary personal residential (PRES) business in FL

  • Participated in first

personal residential assumption from FL Citizens

2013

  • Formed Contractors’ Alliance

Network (CAN) in FL, Heritage’s vendor managed repair program

  • Formed Osprey, a captive

reinsurer.

  • Retroactive quota share

reinsurance agreement with Citizens

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

2016 2015 2017 2018

  • Initiated quarterly

cash dividend

  • Acquired Zephyr, a wind‐only HO

insurer in HI

  • Began writing PRES in NC & SC,

beginning of multi‐state expansion

  • Launched GL insurance in FL
  • Commenced Nat Gen partnership
  • AoB begins to meaningfully impact

results

  • Final year Heritage participated in

Citizens assumptions

  • Began writing PRES in

GA and AL

  • Sawgrass Mutual policy

assumption

  • Acquired NBIC, a coastal

HO insurer in NY, NJ, CT, RI & MA

  • 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

September 2019 Investor Presentation

2019

  • Began writing PRES in VA
  • Began writing CRES in NJ

(first CRES expansion

  • utside FL)
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EXPERIENCED MANAGEMENT TEAM

Bruce Lucas: Chairman & CEO

  • Co‐founded Heritage in 2012 and

has been with the company since inception

  • Prior to Heritage, Mr. Lucas was

CEO of Infinity Investment Funds, a value‐oriented hedge fund

  • Before that, Mr. Lucas was an

attorney with Weil, Gotshal & Manges where he represented large institutional clients such as Enron and GE 7 Richard Widdicombe: President

  • Co‐founded Heritage in 2012 and has

been with the company since inception

  • Prior

to Heritage, Mr. Widdicombe served as Risk Manager of Homeowners Choice Property & Casualty Insurance Company

  • Before

that, Mr. Widdicombe was President of People’s Trust Insurance Company and previously served as president of FedNat, both of which are Florida‐based property insurers Ernie Garateix: Chief Operating Officer

  • Has been in his current role since

2014, prior to which he served as Executive Vice President since the company’s 2012 founding

  • Prior

to Heritage, Mr. Garateix served as Vice President

  • f

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 Arash Soleimani: Executive Vice President

  • Has been in his current role since 2018
  • Prior to Heritage, Mr. Soleimani was a

sell‐side equity research analyst covering the P&C insurance sector at Keefe, Bruyette & Woods (KBW) and Stifel Financial

  • Before that, Mr. Soleimani worked in

Deloitte’s Audit & Enterprise Risk Services division

  • Mr. Soleimani is a CFA charterholder

and a licensed CPA 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

  • ther

insurance enterprises including Marsh & McLennan Companies

  • Mr. Jones holds the American Risk

Manager (ARM) and Certified Property Insurance Adviser (CPIA) designations September 2019 Investor Presentation

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VERTICALLY INTEGRATED STRUCTURE

  • Unique, vertically integrated structure reduces our reliance on third parties, benefiting our loss, LAE and
  • perating 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.)

8

Heritage Insurance Holdings, Inc. (NYSE: HRTG) Heritage Property & Casualty Insurance Company (HPCIC) NBIC Holdings, Inc NBIC Financial Holdings, Inc. Narragansett Bay Insurance Company (NBIC) NBIC Service Company Westwind Underwriters, Inc. Zephyr Acquisition Company HI Holdings, Inc. Zephyr Insurance Company, Inc. (ZIC) Heritage MGA, LLC Heritage Insurance Claims, LLC Contractors’ Alliance Network (CAN) Osprey Re Ltd. First Access Insurance Group, LLC Skye Lane Properties, LLC Risk bearing entity (AL, GA, FL, MS, NC, SC) Risk bearing entity (CT, RI, MA, MD, PA, NY, NJ, VA) Risk bearing entity (HI) Captive reinsurer Provides HPCIC & ZIC with underwriting, personnel and other services Provides NBIC with underwriting, personnel and other services Subsidiary that owns Heritage’s corporate headquarters Mitigation and construction division, serves as a hedge in catastrophe years

ORGANIZATIONAL STRUCTURE

September 2019 Investor Presentation

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SLIDE 9

FL PRES, 44.3% FL CRES, 8.0% NY, 19.8% NJ, 7.7% MA, 6.6% HI, 5.8% Other, 7.8%

PREMIUM SPREAD

BOOK OF BUSINESS

As of 2Q2019, we have $922.5 million of gross premiums in‐force across three statutory insurance entities (Heritage/NBIC/Zephyr) and write two main lines of business, including personal residential (PRES) and commercial residential (CRES). We also write some commercial general liability (CGL)

  • insurance. We’re actively writing in twelve states, but have licenses in sixteen.

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PRES = personal residential • CRES = commercial residential • CGL = commercial general liability • TIV = total insured value

3 Statutory Insurance Entities:

HI AL, FL, GA, MS, NC, SC CT, DE, MA, MD, PA, NJ, NY, RI, VA Includes: PRES in AL, CT, GA, NC, RI, SC & NJ CRES September 2019 Investor Presentation

= actively writing = licensed FL PRES 23.9% FL CRES 6.4% NY 28.6% NJ 12.0% HI 10.5% MA 8.7% Other 9.8%

TIV SPREAD

Includes: PRES in AL, CT, GA, NC, RI, SC, FL CGL & NJ CRES

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IN‐FORCE METRICS

Florida property insurance accounts for 52.6% of Heritage’s consolidated gross premiums in‐force, but it only reflects 30.4% of property insurance total insured value (TIV) – the $5.25 Florida PRES average premium per $1,000 of TIV is almost triple the $1.92 non‐Florida average (Florida’s more expensive policies reflect its higher hurricane risk), while the $359,289 Florida PRES average insured value is well below the $769,121 average for non‐Florida states (property values in Florida trail those in Heritage’s northeast US states).

10

$359,289 $368,982 $325,649 $7,821,686 $450,486 $769,121 $5.25 $4.10 $9.75 $3.51 $4.88 $1.92

$0.0 $2.0 $4.0 $6.0 $8.0 $10.0 $12.0 $0 $100,000 $200,000 $300,000 $400,000 $500,000 $600,000 $700,000 $800,000 $900,000 $1,000,000 FL PRES FL PRES ex‐TC FL PRES TC CRES FL PRES & CRES Non‐FL PRES Premium/$1K TIV Average insured value per policy

TIV Metrics (Property)

Average insured value (left axis) Premium/$1K TIV (right axis)

September 2019 Investor Presentation

PRES = personal residential CRES = commercial residential TC = Tri‐County (FL)

YE2015 YE2016 YE2017 YE2018 2Q2019 PRES $478.1 $515.9 $850.1 $837.1 $843.8 CRES 113.5 118.6 90.1 82.7 73.6 CGL 0.0 0.8 2.1 3.8 5.2 Total $591.5 $635.3 $942.4 $923.7 $922.5 YE2015 YE2016 YE2017 YE2018 2Q2019 PRES 253,726 318,824 518,957 508,424 511,133 CRES 3,405 3,625 3,100 2,973 2,683 CGL 852 2,393 4,289 5,872 Total 257,131 323,301 524,450 515,686 519,688 YE2015 YE2016 YE2017 YE2018 2Q2019 PRES $72,101.6 $109,888.5 $289,974.2 $296,432.3 $304,278.2 CRES 22,764.1 26,367.4 22,831.7 23,038.2 20,985.6 Total $94,865.7 $136,255.9 $312,805.9 $319,470.5 $325,263.8 IN‐FORCE METRICS ($ in millions ) Gross Premiums In‐Force Policies In‐Force Total Insured Value (Property)

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SLIDE 11

DISTRIBUTION

  • Over 6,000 appointed producers across our multi‐state platform
  • Relationships with multiple auto carriers, whereby the policyholder receives a bundled

product discount.

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Overview NBIC

  • Over 2,300 actively writing independent agents
  • 35% 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 in FL
  • Relationships with multiple auto carriers

HPCIC

  • Roughly 175 retail independent agents representing approximately 500 agency locations
  • 8 wholesale relationships that have access to 1,500 retail locations

Zephyr

  • Relationships with 70 actively writing independent agencies
  • 52% of voluntary premium is written by agents affiliated with three large agency networks

September 2019 Investor Presentation

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REINSURANCE PROGRAM

Heritage has a conservative 2019‐2020 reinsurance program, protecting the Company against hurricanes and severe weather events and reducing earnings volatility.

12

  • Substantial severity and frequency protection.
  • Significantly increased return period to the highest level in the Company’s history.
  • $1.5 billion first event reinsurance exhaustion point in the southeast.
  • Heritage's first event retentions in the southeast and Hawaii remain at $20 million, accounting for

4.6% of second quarter 2019 GAAP equity (pre‐tax), down from 5.2% in the prior year. First event retention increases slightly in the northeast to $13.8 million from $12.8 million in the prior year, but accounts for just 3.1% of second quarter 2019 GAAP equity (pre‐tax), down 20 basis points year‐over‐year.

  • Reduced catastrophe reinsurance spend by $10 million vs. prior year. Total cost to Heritage of

$249.2 million (27.0% of second quarter 2019 premiums‐in‐force), down from $259.5 million (27.9% of second quarter 2018 premiums‐in‐force) last year.

  • Heritage’s third‐party reinsurers are rated “A‐” or higher by A.M. Best or S&P or are fully

collateralized.

September 2019 Investor Presentation

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SLIDE 13

CONSERVATIVE REINSURANCE RETENTION

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Note 1: Based on 2019‐2020 catastrophe reinsurance programs. Note 2: Assumes a modeled 1‐in‐50‐year first event for HPCIC based on 8/31/2019 projections (AIR v6, hurricane only, long term view with demand surge). Note 3: Excludes reinsurance reinstatement premiums and income from vertically integrated operations. Note 4: UVE retention includes both UPCIC & APPCIC and FNHC retention includes both FNIC and MNIC, but excludes PIH. Note 5: Calculation based on 21.0% and 5.5% US federal and Florida statutory corporate income tax rates, respectively. Source: Peer company reports.

3.4% 6.8% 5.9% 6.4% 7.1% 7.6% 0% 1% 2% 3% 4% 5% 6% 7% 8% HRTG FL peer median UVE HCI FNHC UIHC

AFTER‐TAX FIRST EVENT FLORIDA RETENTION AS % OF 2Q2019 GAAP EQUITY

September 2019 Investor Presentation

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SLIDE 14

INVESTMENT PORTFOLIO

Heritage has a very conservative investment portfolio, consisting predominantly of low duration, fixed income

  • securities. As of 2Q2019, duration was 3.3 years, 0.2 years below 1Q2019 and 0.4 years below 2Q2018.

14

US government, 9.8% Munis, 12.7% Special revenue bonds, 43.7% Industrial & misc. bonds, 29.5% Preferred stock, 0.0% Equities, 0.3% Limited partnerships, 3.9%

INVESTMENT PORTFOLIO BREAKDOWN (2Q2019)

September 2019 Investor Presentation

$136.2 $331.2 $400.1 $603.0 $567.0 $526.1 $578.0 1.4% 1.6% 2.0% 1.8% 1.9% 2.4% 2.7% 0.0% 0.5% 1.0% 1.5% 2.0% 2.5% 3.0% $0 $100 $200 $300 $400 $500 $600 $700 2013 2014 2015 2016 2017 2018 1H2019

Net investment income yield Investments ($ in millions)

NET INVESTMENT INCOME PERFORMANCE

Investments (left axis) Net investment income yield (right axis)

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Investment considerations

Heritage Insurance

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VALUE PROPOSITION

  • Currently trading at significant discount to peers, despite attractive relative ROE and income metrics
  • Consistent track record of double‐digit 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 re‐underwriting efforts in Florida’s Tri‐County – including rate

increases, policy form enhancements and conservative policy selection – 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
  • pportunities 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 interest with shareholders
  • CEO owns 4.1% of outstanding shares
  • President owns 2.5% of outstanding shares
  • Total insider ownership = 14.6% of outstanding shares

16

Compelling financial metrics Management has significant skin in the game Growth & underwriting

  • utlooks

improving Prudent capital management Business model designed to reduce earnings volatility

September 2019 Investor Presentation

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UNDERWRITING PERFORMANCE

Heritage has experienced significant premium growth since inception, stemming primarily from Citizens depopulation transactions through 2015 and from M&A and organic growth in subsequent years.

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367.2 478.1 458.6 465.4 450.2 448.5 94.1 113.5 118.6 90.1 82.7 73.6 331.5 337.2 347.0 58.1 55.4 53.5 53.4 $51.6 $200.1 $461.3 $591.5 $635.3 $942.4 $923.7 $922.5

$0 $100 $200 $300 $400 $500 $600 $700 $800 $900 $1,000 2012 2013 2014 2015 2016 2017 2018 2Q2019

IN‐FORCE PREMIUM

HPCIC ex CRES FL CRES NBIC Zephyr September 2019 Investor Presentation

Heritage’s premium growth is unprecedented, reaching almost $1 billion of gross in‐force premiums 5 years after the company’s founding. The modest premium declines in 2018 and 1H2019 stemmed from Tri‐County FL exposure reduction efforts in response to assignment‐of‐benefits (AoB), litigation abuse and FL CRES de‐risking.

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SLIDE 18

UNDERWRITING PERFORMANCE (CONTINUED)

Heritage’s underwriting operation has outperformed peers almost every year since inception.

18

Note 1: Peers include FNHC, HCI, KINS, UIHC & UVE Source: FactSet and peer company reports 40.5% 40.1% 37.5% 58.0% 53.1% 52.3% 61.0% 32.4% 31.3% 27.5% 34.8% 41.0% 38.1% 40.3% 72.9% 71.4% 65.0% 92.8% 94.1% 90.4% 101.3% 87.8% 77.1% 79.9% 84.6% 104.7% 94.8% 106.0%

‐5% 15% 35% 55% 75% 95% 115% 0% 20% 40% 60% 80% 100% 120% 2013 2014 2015 2016 2017 2018 1H2019

SOLID UNDERWRITING MARGINS

Loss ratio (left axis) Expense ratio (left axis) Peer median (right axis)

Citizens takeouts benefit HRTG’s margins Tornadoes, Hurricanes Hermine & Matthew, AOB Hurricane Irma & AoB Hurricanes Lane, Florence & Michael, AoB Southeast hail and wind storms

September 2019 Investor Presentation

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CAPITAL MANAGEMENT & OPERATING LEVERAGE

Heritage has been a responsible steward of shareholder capital and currently has $42.7 million remaining on its share repurchase authorization. Since 2016, the Company has returned $80 million to shareholders through common share repurchases and dividends. Heritage’s ratio of trailing‐twelve‐month (TTM) net premiums written to 2Q2019 equity is only 0.9x , among the lowest in its peer group, which is indicative of its conservative balance sheet. Looking ahead, Heritage has adequate capital to fuel its premium growth and multi‐state expansion initiatives.

19

7.0 6.5 6.4 3.6 25.6 21.6 2.0 7.3 25.2 18.0 11.6 $32.6 $53.3 $26.4 $22.5 20.7% 15.7% 23.5% 46.8% 0% 5% 10% 15% 20% 25% 30% 35% 40% 45% 50% $0 $10 $20 $30 $40 $50 $60 2016 2017 2018* 1H19*

$ in millions

DISCIPLINED CAPITAL MANAGEMENT

Dividends Share repurchase Debt repurchase Div payout ratio (right axis) 0.5 0.9 1.1 1.3 1.4 1.4 1.5 1.7 0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6 1.8 PLMR HRTG HCI UIHC Peer median UVE KINS FNHC

Net operating leverage (NPW/Equity)

CONSERVATIVE NET OPERATING LEVERAGE

*2018 and 1H19 debt repurchases are net of new debt and stock issued in connection with refinancing transactions.

September 2019 Investor Presentation

Source: Peer company reports.

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SLIDE 20

41.1% 32.4% 40.3% 27.5% 17.8% 6.6% 5.5% 4.9% 25.7% 15.4% 11.5% 3.8% 2.9% 2.4% 58.9% 67.6% 34.0% 57.1% 41.3% 21.7% 23.3% 23.1%

100.0% 100.0% 100.0% 100.0% 70.6% 32.1% 31.6% 30.4%

0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 100% 4Q12 4Q13 4Q14 4Q15 4Q16 4Q17 4Q18 2Q19

% OF CONSOLIDATED PROPERTY TOTAL INSURED VALUE (TIV) IN FLORIDA

Personal Residential: Tri‐County, FL Commercial Residential: Tri‐County, FL Other FL

DIVERSIFICATION STRATEGY UNDERWAY

20

Through a combination of M&A and organic growth, Heritage has been diversifying its book of business to new states, resulting in a better spread of risk and lower reinsurance costs. Diversification has been

  • ccurring within the FL book too, as Heritage has

steadily been reducing its personal residential (PRES) & commercial residential (CRES) exposure to Tri‐ County, FL (TC). PRES exposure reduction in TC is intended to limit exposure to AoB and litigation abuse, while CRES reduction in TC is intended to reduce concentration risk in the event of a storm.

September 2019 Investor Presentation

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SLIDE 21

35% 38% 37% 41% 46% 45% 45% 49% 52% 49% 52% 54% 44% 39% 33% 31% 34% 31% 0% 10% 20% 30% 40% 50% 60% 1Q15 2Q15 3Q15 4Q15 1Q16 2Q16 3Q16 4Q16 1Q17 2Q17 3Q17 4Q17 1Q18 2Q18 3Q18 4Q18 1Q19 2Q19

LITIGATED NON‐HURRICANE CLAIMS AS % OF TOTAL CLAIMS

FAVORABLE CLAIMS TRENDS

Heritage’s Tri‐County, FL (TC) exposure reduction efforts are bearing fruit, as the region’s contribution to open non‐hurricane claim counts continues to decline for both litigated and non‐litigated claims. This is benefiting

  • verall claims trends – beginning with 1Q18, litigated claims have generally been accounting for a smaller

percentage of Heritage’s non‐hurricane open claims inventory.

21 A decline in litigated claims should benefit underwriting margins, given that litigated claims are typically more expensive to resolve Tri‐County, FL (TC) claims are typically more expensive given the prevalence of assignment of benefits and litigation abuse in the region

Note: Excludes NBIC.

September 2019 Investor Presentation 31% consists of 50% in TC and 20% elsewhere, illustrating rationale behind TC de‐risking

84% 82% 81% 82% 82% 79% 80% 79% 79% 79% 79% 78% 77% 73% 67% 66% 63% 61% 51% 47% 46% 58% 55% 52% 54% 56% 55% 55% 55% 51% 49% 44% 41% 39% 38% 27% 0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 1Q15 2Q15 3Q15 4Q15 1Q16 2Q16 3Q16 4Q16 1Q17 2Q17 3Q17 4Q17 1Q18 2Q18 3Q18 4Q18 1Q19 2Q19

TRI‐COUNTY FL NON‐HURRICANE CLAIMS TRENDS

Tri‐County, FL open litigated claims as % of total open litigated claims (non‐hurricane) Tri‐County, FL open non‐litigated claims as % of total open non‐litigated claims (non‐hurricane)

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SLIDE 22

SOLID BOOK VALUE PER SHARE GROWTH

22

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 27% since the Company’s 2012 inception.

$3.38 $7.20 $8.56 $11.71 $12.41 $14.67 $14.43 $14.99 $0.05 $0.29 $0.53 $0.77 $0.95

$3.38 $7.20 $8.56 $11.76 $12.70 $15.20 $15.20 $15.94 $0 $2 $4 $6 $8 $10 $12 $14 $16 $18 2012 2013 2014 2015 2016 2017 2018 2Q2019

SOLID GROWTH IN BOOK VALUE AND CUMULATIVE DIVIDENDS PER SHARE

Book Value Per Share Cumulative Dividends Per Share September 2019 Investor Presentation

slide-23
SLIDE 23

ABOVE‐PEER ROE, BUT BELOW‐PEER VALUATION

23

TRADING AT A MEANINGFUL DISCOUNT TO PEERS SOLID ROE PERFORMANCE, EVEN IN HURRICANE YEARS

* HRTG’s 2017 ROE metrics are non‐GAAP and adjusted to exclude a $42.2 million non‐cash, non‐tax deductible charge related to the mark‐to‐market of a derivative liability associated with the Company’s convertible

  • debt. The derivative liability was reclassified to equity in 4Q17.

Source: FactSet and peer company reports

9.1% 15.9% 8.7% 8.9% 0% 2% 4% 6% 8% 10% 12% 14% 16% 18% Return on Equity Average Return on Tangible Equity

2016‐2018 AVERAGE RETURN ON EQUITY VS. PEERS

HRTG* Peer Median

HRTG’s average ROE over the last 3 years has outperformed by 40 bps. HRTG’s average ROTE over the last 3 years has

  • utperformed by 700 bps.

1.0x 1.4x 0.7x 1.0x 1.1x 1.7x 1.8x 4.5x 0.0x 0.5x 1.0x 1.5x 2.0x HRTG Peer median FNHC UIHC KINS UVE HCI PLMR

PRICE/BOOK VALUE

8.4x 9.7x 5.3x 9.1x 9.4x 10.0x 11.1x 19.4x 0x 2x 4x 6x 8x 10x 12x 14x 16x HRTG Peer median FNHC KINS UVE UIHC HCI PLMR

PRICE/2019E EPS

HRTG’s P/E multiple is at a 14% discount to peers

28.1% 30.3% 9.5% 11.1% 6.7% 3.6% 0% 5% 10% 15% 20% 25% 30% 35% 2014 2015 2016 2017* 2018 1H2019

RETURN ON AVERAGE EQUITY

Citizens depopulation transactions benefit ROEs Severe 1Q16 FL tornadoes, Hurricanes Hermine & Matthew Hurricane Irma Active northeast US weather & Hurricanes Lane, Florence & Michael Assignment of benefits (AoB) abuse Southeast hail and wind storms

September 2019 Investor Presentation

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SLIDE 24

$438 $568 $0 $100 $200 $300 $400 $500 $600 HRTG UIHC

MARKET CAP ($ in millions)

HIGHLY ATTRACTIVE VALUATION RELATIVE TO PEERS

HRTG’s large valuation discount doesn’t correspond to its returns relative to peers 24

*HRTG’s 2017 net income and ROE are non‐GAAP and adjusted to exclude a $42.2 million non‐cash, non‐deductible charge related to the mark‐to‐market of a derivative liability associated with the Company’s convertible debt. The derivative liability was reclassified to equity in 4Q17. Please see slide 24 for a reconciliation of HRTG’s non‐GAAP measures to their comparable GAAP measures.

Despite consistently generating more net income, HRTG* has a lower market capitalization than UIHC.

Source: FactSet and peer company reports

$47.1 $92.5 $33.9 $41.1 $27.2 $7.7 $41.0 $27.4 $5.7 $10.1 $0.3 $6.8 $0 $10 $20 $30 $40 $50 $60 $70 $80 $90 $100 2014 2015 2016 2017* 2018 1H2019

NET INCOME ($ in millions)

HRTG* UIHC

Impact of net unrealized losses on equities on 2018 net income (NI) assuming a 25% tax rate: UIHC: $(9.3) million PT, $(7.0) million AT HRTG: $(2.1) million PT; $(1.6) million AT Impact of net unrealized gains on equities on 1H2019 NI assuming a 25% tax rate: UIHC: $12.9 million PT, $9.7 million AT HRTG: $2.7 million PT; $2.0 million AT

Source: FactSet and peer company reports Note: PT = pre‐tax; AT = after‐tax Source: FactSet and peer company reports

September 2019 Investor Presentation

Ticker Company 2019E 2020E Current 2019E 2020E 2016 2017 2018 2019E 2020E 2016 2017 2018 HRTG Heritage Insurance Holdings, Inc. 14.5 8.4 0.98 0.94 0.86 9.5% 11.1% 6.7% 6.7% 10.7% 10.7% 20.0% 16.9% FNHC FedNat Holding Company 10.6 5.3 0.74 0.73 0.63 0.5% 3.7% 7.0% 7.2% 12.8% 0.5% 3.7% 7.0% HCI HCI Group, Inc. 15.2 11.1 1.82 1.84 1.76 12.1%

  • 3.1%

9.4% 12.4% 16.2% 12.2%

  • 3.2%

9.7% UIHC United Insurance Holdings Corp. 24.8 10.0 1.05 1.03 0.97 2.4% 2.6% 0.1% 4.3% 10.0% 2.5% 3.2% 0.1% UVE Universal Insurance Holdings, Inc. 10.3 9.4 1.71 1.77 1.62 29.9% 26.4% 24.9% 18.1% 18.0% 30.0% 26.5% 25.0% KINS Kingstone Companies, Inc. NA 9.1 1.10 1.04 0.96 17.5% 13.2% 3.4%

  • 1.2%

10.9% 18.0% 13.4% 3.4% PLMR Palomar Holdings, Inc. 22.9 19.4 4.46 3.96 3.34 17.5% 13.2% 3.4% 21.7% 18.7% 18.0% 13.4% 3.4% Ex-HRTG coastal property median 15.2 9.7 1.40 1.40 1.29 14.8% 8.5% 5.2% 9.8% 14.5% 15.1% 8.6% 5.2% HRTG vs. ex-HRTG coastal property median

  • 4.3%
  • 14.0%
  • 30.3%
  • 33.1%
  • 33.8%
  • 5.3%

2.7% 1.6%

  • 3.1%
  • 3.8%
  • 4.4%

11.4% 11.7% P/E P/BV Return on Average Equity Return on Tangible Equity

slide-25
SLIDE 25

APPENDIX: NON‐GAAP RECONCILIATIONS

25

RECONCILIATION OF GAAP AND NON‐GAAP MEASURES $ in millions 2017 GAAP Net income (loss) (1.1) $ Conversion option liability fair value 42.2 Non‐recurring business acquisition related expenses ‐ Tax impact ‐ Adjusted net income 41.1 $ 2017 GAAP ROE ‐0.3% Conversion option liability fair value 11.4% Non‐recurring business acquisition related expenses 0.0% Tax impact 0.0% Adjusted ROE (non‐GAAP) 11.1%

September 2019 Investor Presentation

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SLIDE 26

Arash Soleimani, CFA, CPA Executive Vice President asoleimani@heritagepci.com 727.871.0206 Website: investors.heritagepci.com

ADDITIONAL INFORMATION