Exhibit 99.1

 

Investor Presentation Fourth Quarter 2019

2 Table of Contents We believe our expertise, differentiation and the value we can provide to a customer will result in sustainable profitability over the long term. Larry Hannon, CEO & President 03 Summary Information 04 The ProSight Story 08 Business Execution 17 Financial Strength 22 Appendix

3 Summary Information 1 Adjusted operating ROE is a non - GAAP measure. See Appendix for reconciliation of net income to adjusted operating income 2 Market cap calculated off of closing stock price on February 25, 2020 3 As of December 31, 2019 and excludes terminated niches and other. Other for 4Q 2019 (TTM) GWP was $68M. Other includes GWP from certain niches that are no longer part of our ongoing business. All GWP from exited niches are included in “Other” which consists of ( i ) primary and excess workers’ compensation coverage for Self - Insured Groups (ii) niches exited prior to 2018, many with a concentration in commercial auto, (iii) certain fronting arrangements in which all premium written is ceded to a third party, (iv) participation in industry pools, and (v) emerging new business customer segments. Rating A - (Excellent) by A.M.Best Niche Programs 41 (as of 4Q 2019) Customer Segments 8 (as of 4Q 2019) • Founded in 2009 • Began generating GWP in 2011 • Headquartered in Morristown, NJ • Five office locations nationwide • 396 employees across the U.S. • Publicly traded on the NYSE under ticker symbol “PROS” We are PROS Adjusted Operating ROE 1 12.4% (Q4 YTD) Market Cap 2 $613M (stock price: $14.24/share) Annual Gross Written Premium (TTM) 3 $900M

The ProSight Story Who we are, where we’ve been, and how we make a difference

5 We are experts that focus on and specialize in niches Our focus on alignment by customer niche is how we make a difference • Our team - oriented, results - driven culture is built around supporting our customers • Focus on customer niches: refined homogeneous groups of customers with limited fragmentation • Differentiate through innovative products, services and third - party solutions • Our underwriting expertise helps drive our profitability • We strive to provide the best customer experience in the business — coupling technology with a human touch • Partner with expert, limited distribution and institutionalize those relationships OUR FOUNDING PRINCIPLES ProSight was built on the foundation that insurance companies can, and should, provide valuable solutions to customers — solutions that truly address customers’ unique business needs. What we BELIEVE • Our structure and expertise around the customer niche enable us to create solutions for our customers that help their business thrive • We deliver our offerings through limited and expert distribution partners specific to each customer niche • Our profit - first underwriting philosophy and disciplined approach to growth contribute to our financial strength What we DO We are PROS Our Story

6 Our Management Team Larry Hannon CEO & President Bob Bailey Chief Underwriting & Risk Officer Buddy Piszel Chief Financial Officer Rob Bednarik Customer Segment President Darryl Siry Chief Tech & Ops Officer Donna Biondich Chief Claims Officer Nestor Lopez Chief Information Officer Vivienne Zimmermann Chief CX Officer Frank Papalia Chief Legal Officer Joe Finnegan Customer Segment President Lee Kraemer Chief Actuarial Officer Ric Victores Chief Sales & Marketing Officer Kari Hilder Chief HR Officer Erin Cullen Customer Segment President Lee Lloyd Field Operations Officer Kevin Topper Customer Segment President A leadership team with deep industry expertise built from decades of diverse experience:

7 Our History How we’ve grown and why we’re poised to take the next step. 2009 Founded by Joe Beneducci, CEO Larry Hannon, COO Bob Bailey, CUO 2010 Goldman Sachs & TPG Invest Funds in ProSight Acquired NYMagic for $230M 2011 GWP Surpasses $200M 2011 ProSight Opens Glendale CA Office 2013 GWP Surpasses $500M 2014 Featured on Inc. 5000 List of Fastest - Growing Private Companies 2015 GWP Surpasses $750M 2017 GWP Surpasses $830M 2019 Larry Hannon Named CEO & President 2010 ProSight Opens Morristown NJ Office 2016 ProSight Online for Customers Launches 2017 ProSight Launches Direct Bill for Customers 2013 ProSight Premiere Policy Launches 2019 ProSight Completion of IPO under ticker “PROS” 2019 ProSight Opens Ft. Lauderdale FL Office 2011 ProSight Opens New York NY Office 2012 GWP Surpasses $350M

Business Execution Designed around the customer to deliver results

• Auto Dealers • Franchise Equipment Dealers • Professional Employer Organizations • Restaurants, Bars and Taverns • Social Services • Parking Facilities (NEW) • Snow & Ice Mgmt (NEW) • Animal Welfare (NEW) Sports $30 million • Motor Sports • Sports • Country Clubs • Aquatic Recreation (NEW) • Builders Risk • Hotels • Manufactured Housing • MetroBuilders • Property Managers • Residential • Self Storage (NEW) Real Estate $168 million 14% 13% 15% 11% 13% 19% 3% 12% 9 • Charter Bus • Intermodal Transportation • Propane & Fuel Dealers • School Bus • Taxis Transportation $112 million • Accountants • Credit Unions • Customs Brokers • Lawyers • Pest Control Professional Services $119 million • Construction Managers • Cranes • Federal Contractors • Luxury Home Builders • Marine Contractors • Scaffolding • Specialty Trade Contractors • Ocean Marine • Petroleum Services • Solar Contractors GWP: $900M 2 (trailing twelve months) Niche Focused Specialty Franchise • Live Entertainment • Film Media & Entertainment $125 million Diversified portfolio with 8 customer segments and 41 specialty niches 1 . Consumer Services $134 million Construction $118 million Marine & Energy $94 million 1 As of December 31, 2019 2 Excludes terminated niches and other. Other 4Q 2019 (TTM) GWP was $68M. Aquatic Recreation (NEW)

10 Flexible Distribution Model NOTE: Percentages are based on existing customer segment GWP. 1 TTM as of December 31, 2019. We can reach the customer in various ways: MGUs, retailers, wholesalers, and direct. Customers Limited & Preferred Distribution Partners • 17 niches 1 • Agency contracts appointed for 1 niche • Joint marketing to build brand awareness • ProSight maintains all underwriting authority • 3 niches 1 • ProSight maintains all underwriting authority • Aggregation play consistent with customer behavior • 21 niches 1 with 13 MGUs • Each provides exclusivity of some kind • IP is mutually shared while appointed • ProSight maintains parameters and determines guidelines around all claims • ProSight controls underwriting guidelines and reinsurance purchasing • No channel conflict • ~100 total distribution partners • > 70% GWP on exclusive basis • Ability to write business direct Key Model Highlights [ Breakdown of GWP (%) ] Retail 31% Wholesale 13% MGU 56%

11 Differentiators That Matter SecureFleet ® A customizable video safety system designed to help enhance operational efficiency, reduce litigation costs, and improve driver behavior. Available in Charter Bus, Cranes, Intermodal Transportation, Petroleum Services and Taxis niches . Music Mends ℠ An endorsement that provides partial indemnity for bands or performers whose tour schedule was interrupted by an act of terror, enabling them to circle back and play for the affected community. Available in Live Entertainment niche. R.I.C.H ℠ Coverage Our complimentary R.I.C.H. (release of information during construction of customer’s home) endorsement that provides insureds with the means to resolve an incident, while protecting against reputational harm. Available in Construction Managers, MetroBuilders, and Luxury Home Builders niches. PolicyTracks ℠ Enables general contractors to collect and track subcontractor policies, insurance certificates, endorsements and subcontractor agreements. Available in Construction Managers, MetroBuilders, and Luxury Home Builders niches. Some differentiator examples include: Customer focus + differentiation = real value for customers “We take a disciplined approach to our growth, choosing to enter niches where our differentiation matters to a customer.” — Bob Bailey, Chief Underwriting & Risk Officer Our customers are unique, so our solutions need to be too. We believe our “ differentiators” are unique to ProSight and deepen our relationship with the customer. They are built to improve retention of business and are part of our competitive moat. Often developed by ProSight in conjunction with customers and distribution partners, these differentiators are designed to provide customer value by protecting and enhancing their business.

12 Customer Experience Built for Today Designed for what our customers need. Strive to provide best - in - class service • Rapid Emergency Response: On hand expert emergency service sent to mitigate damage • ProSight Mobile: Fast and simple incident reporting from any device Claims Reporting Our systems are built to be accessible • ProSight Online: Powerful online customer portal for insureds and partners • ProSight Premiere: Fully custom policy administration & billing system 24 / 7 Portal Access There to help our customers • Over 99% “Awesome / Good” customer experience rating 1 • Unscripted Support — licensed, real and ready to help Contact Center “I expect and always receive outstanding service from ProSight Claims, but this was easy, seamless, and better than outstanding! Thank you!” — Claire B, Broker “We are thrilled with the updates you’ve made to your systems. We feel like this will cut down on a lot of our follow - ups to the insureds after they submit a loss.” — Stephanie B, Partner “Every time I call ProSight, it is a wonderful experience; from the patience they offer to answering all of my questions to the enthusiasm they have over the phone.” — Armani L, Broker Real Testimonials Our goal is to provide our insureds and partners with the best service possible. 1 92% “Awesome” rating and 7% “Good” rating based on 2019 Qualtrics Survey Data

SYSTEMS INCLUDE 13 Innovative Proprietary Technology Platform Developed by us, for us, with the customer experience in mind • Modern, scalable, and digitally - enabled technology platform that simplifies and improves the insurance buying process and user experience, while allowing us to better manage our business. • Utilize cutting - edge systems: We employ a single policy administration/billing system, incident - reporting system, and reinsurance system • Proprietary dashboards deliver insight for day - to - day business decisions on a real - time basis • Strong mobile development capabilities allow customers and agents to interact with us easily and efficiently Customer Focused ProSight Online Customer Policy Access ProSight Mobile Incident Reporting App ProSight API Application Programming Interface ProSight Direct Direct - to - Customer Platform Underwriting / Operational ProSight Premiere Policy Administration & Billing ClimberPortal Employee Training & Development PATI ProSight Artificial Textual Intelligence Chatbot ProSight Climber GPS Financial Monitoring & Reporting “ProSight’s technology and operational platform drives efficiency while supporting the unique needs of our niche business strategy and delivering a tailored experience for customers.” — Darryl Siry, Chief Technology & Operations Officer

14 “We constantly evaluate our underwriting portfolio to ensure it is best positioned for long - term profitability.” — Larry Hannon, CEO & President

Calendar Year Loss Ratio Accident Year Loss Ratio Catastrophic Loss 72.4% 63.9% 59.6% 61.4% 63.5% 61.0% 60.3% 61.6% 2016 2017 2018 2019 1.2% 1.3% 0.4% 15 Profitable Underwriting We focus on profitable underwriting, including loss ratio stability and a goal of expense ratio improvement • Inception - to - date (2011 to 2019) GAAP loss ratio of 63.8% for all business and 60.8% for existing customer segments • Selective entry (and exit) of niches is a part of our underwriting strategy • Purposeful historical low catastrophic loss exposure 1 — since 2011, catastrophic losses 1 have averaged less than 1.0 basis point. • ProSight expects 200 basis points of expense ratio improvement from 2019 by YE 2022 1 Catastrophe losses and LAE are any one claim, or group of claims, equal or greater than $1M related to a single PCS® designat ed catastrophe event. 2 GWP as of Q4 YTD 3 Expense ratio shown is Adjusted Expense Ratio. See “Factors Affecting our Results of Operations (WAQS)” in the Appendix NOTE: Loss Ratios as presented, adjusted for Whole Account Quota Share, except where otherwise noted. See “Factors Affecting our Results of Operations (WAQS)” in the Appendix General Liability 30% Commercial Auto 22% Primary Workers Comp 13% Misc. Lines 10% Property 13% Prof. Liability 6% Umbrella 6% Diversified by Line of Business 87% 13% 81% 19% - Casualty 2 - Property 1 - Admitted 2 - Non - Admitted (E&S) 2 Expense Ratio 3 35.8% 34.9% 37.0% 36.6% 2016 2017 2018 2019 Loss Ratio 0.5%

$55.0 $73.4 $101.9 $117.9 $95.0 $94.4 $107.1 $133.7 $66.2 $79.2 $83.0 $94.1 $103.7 $114.4 $119.9 $124.9 $79.8 $112.6 $110.5 $119.3 $102.1 $132.0 $132.7 $167.6 $17.8 $22.2 $23.6 $30.1 $ 90.2 $ 85.1 $ 92.2 $ 112.2 2016 2017 2018 2019 Transportation Sports Real Estate Professional Services Media and Entertainment Marine and Energy Consumer Services Construction $609.8M 1 $713.3M 1 $770.9M 1 16 Strong Premium Growth 1 Existing customer segment only; actual GWP are $772M for 2016, $836M for 2017, $895M for 2018, and $968m for 2019 2 CAGR for actual GWP from 2016 to 2019 is 7.8%. Future growth within any niche or customer segment considers profitability first . ProSight employs a rigorous process to identify if/when growth is justified and react quickly once a decision is made. Growth in Existing Niches New Customer Segments New Niches in Existing Customer Segments WE GROW IN THREE WAYS: Existing Customer Segments Only $899.8M 1

Financial Strength Our backbone for sustainable value creation (updated for 4Q 2019)

1,327.7 42.1 24.2 12.8 Total Net Loss Reserves Exited Niches UK Exposure A&E Exposures 38% 15% 24% 2% 3% 6% 12% General Liability Commercial Auto Excess WC Property Misc Lines Prof Liability Primary WC Net Loss Reserve Detail at 12/31/2019 ($ in millions) 18 Prudent Loss Reserve Position Sound loss reserve position • Total net loss reserves of $1.3 billion • Exited niches excluding Excess Workers’ Compensation business ($42.1M of net loss reserves) and A&E exposures ($12.8M of net loss reserves) are not significant to aggregate reserves • Duration of loss reserves: 5.2 years 0.7% 0.8% 0.8% 0.5% 0.2% 2.4% (1.9%) 1Q18 2Q18 3Q18 4Q18 1Q19 2Q19 3Q19 4Q19 Net Loss Reserves by Line of Business (%) Net Reserve Development 1Q18 - 4Q19 (fav / (unfav) %) NOTE: All financial information as of Dec 31, 2019, unless otherwise noted. ** The ratio above represents development over NEP for the quarter 0.0%

19 Diversified & Conservative Investment Portfolio • $2.2 billion conservatively managed investment portfolio • Predominantly fixed income securities (93.1% of cash and total investments) • Greater than 60% of fixed income securities rated “A” or better and a 3.4 year weighted average duration • 16.0% portfolio CAGR from 2016 through 2019 • 3.4% net yield Fixed Income Securities 93.1% Short - term Investments 2.0% Cash and Cash Equivalents 1.3% Commercial Levered Loans 0.6% Limited Partnerships and LLCs 3.0% U.S. Gov't & Gov't Agency 2.8% Corporate Securities 65.6% Municipals 3.9% ABS 3.6% CLO 8.8% CMBS 4.8% RMBS 10.5% A 35.2% AA 17.5% AAA 10.8% BBB 27.6% Below BBB/ Not Rated 8.9% 28.1 36.2 56.0 68.9 2016 2017 2018 2019 NOTE: All financial information as of Dec 31, 2019, unless otherwise noted. Maximizing investment income while minimizing volatility Net Investment Income ($ in millions) Investment Portfolio Composition Fixed Income Securities (by type) Fixed Income Securities (by rating) NOTE: ProSight outsources investment management to leading 3 rd - party fixed income managers.

20 Shareholder Value Creation Sustainable and consistent financial trajectory • Double - digit ROE over past two years • Debt - to - capital position allowing for capital strategy flexibility • NWP - to - Equity of 1.6x • Capital Raise of ~$51M from IPO (July 2019) • Debt - to - capital position decreased from 31.9% in 2018 to 23.3% in 2019 $0.41 $0.37 $1.40 $1.39 2016 2017 2018 2019 1 Adjusted operating income and adjusted operating ROE are non - GAAP measures. See Appendix for reconciliation of net income to adjusted operating income. Adjusted Operating Income 1 per Diluted Share ($) Book Value per Diluted Share ($) Adjusted Operating Return on Equity 1 (%) - 3.6 3.7 14.4 12.4 2016 2017 2018 2019 $ 10.74 $ 9.71 $ 9.88 $ 12.01 2016 2017 2018 2019

21 Disclaimer Important Notice This presentation contains forward - looking statements. Forward - looking statements include statements relating to future developm ents in our business or expectations for our future financial performance and any statement not involving a historical fact. Forward - looking statements use words such as “anticipate,” “believe,” “estimate,” “expect,” “intend,” “plan,” “should,” “seek,” and other words and term s o f similar meaning. Forward - looking statements are subject to known and unknown risks and uncertainties, many of which may be beyond our c ontrol. We caution you that forward - looking statements are not guarantees of future performance or outcomes and that actual performance and outcomes may differ materially from those made in or suggested by the forward - looking statements contained in this presentation. In addition, even if our results of operations, financial condition and cash flows, and the development of the market in which we operate, ar e consistent with the forward - looking statements contained in this presentation, those results or developments may not be indicative of resul ts or developments in subsequent periods. New factors emerge from time to time that may cause our business not to develop as we exp ect , and it is not possible for us to predict all of them. For a discussion of some of the risks and important factors that could affect ou r future results and financial conditions, see our filings with the U.S. Securities and Exchange Commission, including, but not limited to, the ri sks and uncertainties included under the caption “Risk Factors”. Except as required by law, we undertake no obligation to publicly u pda te any forward - looking statements, whether as a result of new information, future events or otherwise. Presentation of Financial Information This presentation includes certain “non - GAAP” financial measures that either exclude or include amounts that are not excluded or included in the most directly comparable measures calculated and presented in accordance with generally accepted accounting principles in th e United States (“GAAP”). The non - GAAP financial measures used in this presentation are adjusted operating income, adjusted operating ret urn on equity, and adjusted loss ratio. These non - GAAP financial measures should not be considered in isolation or viewed as a substit ute for their most directly comparable GAAP figures. Other companies may calculate such non - GAAP financial measures differently. Accordingly, these measures may not be comparable to similarly titled measures of other companies. See the Appendix for a reconciliation of thes e n on - GAAP financial measures to the most comparable GAAP figures.

Appendix Q4 2019

23 Contacts Media & Public Relations Joe Hathaway 973 - 532 - 1706 jhathaway@prosightspecialty.com Investor Relations Dean Evans 862 - 505 - 5187 devans@prosightspecialty.com Corporate Headquarters 412 Mt. Kemble Avenue, Suite 300C Morristown, NJ 07960 973 - 532 - 1900

December 31 September 30 June 30 March 31 2019 2019 2019 2019 2018 2017 2016 Assets (as restated) (as restated) (as restated) Investments: Fixed income securities, available-for-sale at fair value 2,040,682$ 2,025,955$ 1,883,989$ 1,766,478$ 1,693,382$ 1,484,431$ 1,222,234$ Commercial levered loans at amortized cost 14,069 14,601 16,549 16,796 16,915 24,500 29,834 Limited partnerships and limited liability companies at fair value 66,660 65,322 62,351 55,835 53,432 41,603 33,383 Short-term investments 43,873 14,398 49,824 69,007 36,661 4,223 44,922 Total investments 2,165,284 2,120,276 2,012,713 1,908,116 1,800,390 1,554,757 1,330,373 Cash and cash equivalents 17,284 24,577 34,241 34,099 22,279 59,397 75,211 Restricted cash 10,213 7,451 8,929 8,201 7,621 18,475 – Accrued investment income 13,610 13,452 13,314 12,508 12,279 9,409 5,353 Premiums and other receivables, net 190,004 179,920 196,128 196,490 200,347 184,334 168,378 Reinsurance receivables paid 3,481 5,849 9,927 15,867 12,428 17,220 28,876 Reinsurance receivables unpaid 193,952 213,977 210,021 201,889 185,295 201,156 176,651 Deferred policy acquisition costs 98,812 103,542 101,740 100,381 93,613 60,759 76,572 Prepaid reinsurance premiums 42,861 47,285 59,218 64,127 44,626 122,950 30,896 Net deferred income taxes 4,803 9,361 13,724 23,674 33,239 37,068 76,784 Goodwill and net Intangible assets 29,189 29,196 29,204 29,211 29,219 29,249 29,745 Fixed assets and capitalized software, net 37,167 37,679 38,145 38,563 39,001 37,834 33,068 Funds withheld related to sale of affiliate 19,453 19,566 19,534 19,309 19,397 26,988 – Other assets 29,537 31,255 33,328 30,988 57,653 37,159 24,765 Assets of discontinued operations 21,584 20,098 19,278 19,607 19,719 12,697 194,831 Total assets 2,877,234$ 2,863,484$ 2,799,444$ 2,703,030$ 2,577,106$ 2,409,452$ 2,251,503$ Liabilities Unpaid losses and loss adjustment expenses 1,521,648$ 1,515,224$ 1,483,660$ 1,449,535$ 1,396,812$ 1,258,237$ 1,166,619$ Reserve for unearned premiums 483,223 472,761 472,907 469,960 435,933 395,432 354,828 Ceded reinsurance payable 17,768 4,099 15,987 15,552 13,281 18,448 2,816 Notes payable, net of debt issuance costs 164,693 164,609 182,517 182,439 182,355 164,017 163,678 Funds held under reinsurance agreements 58,855 68,243 72,362 77,786 63,165 112,260 20,589 Other liabilities 56,438 81,029 91,293 58,812 73,474 71,014 21,522 Liabilities of discontinued operations 31,578 26,936 21,768 22,021 22,256 14,061 140,796 Total liabilities 2,334,203 2,332,901 2,340,494 2,276,105 2,187,276 2,033,469 1,870,848 Shareholders’ equity Common stock, $0.01 par value 431 430 389 389 389 389 389 Paid-in capital 661,761 661,357 603,163 603,163 607,589 606,672 555,589 Accumulated other comprehensive income (loss), net of taxes 37,453 33,930 28,844 5,437 (22,315) 19,298 29,482 Retained deficit (156,414) (164,934) (173,246) (181,864) (195,304) (249,847) (204,271) Treasury shares - at cost (12,920 shares) (200) (200) (200) (200) (200) (200) (200) Total shareholders’ equity 543,031 530,583 458,950 426,925 389,830 375,983 380,655 Total liabilities and shareholders’ equity 2,877,234$ 2,863,484$ 2,799,444$ 2,703,030$ 2,577,106$ 2,409,452$ 2,251,503$ December 31 24 Balance Sheet Note: For informational purposes only and should be read in conjunction with documents filed by ProSight Global, Inc. with th e S ecurities and Exchange Commission, including the most recent prospectus on Form S - 1 and Quarterly Reports on Form 10 - Q. Unaudited

25 Income Statement NOTE: Quarterly income statement reported, not audited. 2019 2018 2019 2018 2019 2018 2019 2018 2019 2018 2017 2016 Revenues: Net premiums earned 207,311$ 193,098$ 202,455$ 187,108$ 202,480$ 183,123$ 195,608$ 167,456$ 807,854$ 730,785$ 609,786$ 675,778$ Net investment income 17,367 12,670 16,974 14,044 17,398 15,548 17,158 13,709 68,897 55,971 36,196 28,052 Realized investment gains (losses) , net 275 (2,362) 245 406 137 686 113 (287) 770 (1,557) 4,204 (6,147) Other income, net 152 169 196 168 97 168 93 168 538 673 853 1,057 Total revenues 225,105 203,575 219,870 201,726 220,112 199,525 212,972 181,046 878,059 785,872 651,039 698,740 Expenses: Net losses and loss adjustment expenses incurred 128,381 113,067 127,196 109,976 127,115 109,933 118,333 101,854 501,025 434,830 393,741 489,464 Policy acquisition expenses 46,712 45,610 45,953 44,195 45,533 43,253 46,573 38,371 184,771 171,429 126,023 152,923 General and administrative expenses 26,497 24,965 25,967 25,051 26,028 24,880 27,194 25,222 105,686 100,118 87,821 88,950 Interest expense 3,070 3,170 3,216 3,092 3,147 3,084 3,362 3,031 12,795 12,377 12,125 12,125 Other expense 1,819 - 7,162 – 7,170 – – – 16,151 – – – Total expenses 206,479 186,812 209,494 182,314 208,993 181,150 195,462 168,478 820,428 718,754 619,710 743,462 Income (loss) from continuing operations before income taxes 18,626 16,763 10,376 19,412 11,119 18,375 17,510 12,568 57,631 67,118 31,329 (44,722) Income tax provision: Current (554) (633) 146 184 82 (397) 141 (7) (185) (853) 864 99 Deferred 4,438 3,932 1,869 3,625 2,341 4,120 3,674 2,565 12,322 14,242 37,369 (24,087) Total income (loss) tax expense (benefit) 3,884 3,299 2,015 3,809 2,423 3,723 3,815 2,558 12,137 13,389 38,233 (23,988) Income (loss) from continuing operations 14,742 13,464 8,361 15,603 8,696 14,652 13,695 10,010 45,494 53,729 (6,904) (20,734) Discontinued operations: Income (loss) from discontinued operations (6,222) 656 (49) (429) (78) (198) (255) 785 (6,604)$ 814$ (37,089) (79,594) Net Income(loss) 8,520$ 14,120$ 8,312$ 15,174$ 8,618$ 14,454$ 13,440$ 10,795$ 38,890$ 54,543$ (43,993)$ (100,328)$ Q1Q2Q3Q4 Year Ended December 31 Unaudited

26 Non - GAAP Reconciliation NOTE: Quarterly income statement reported, not audited. 2019 2018 2019 2018 2019 2018 2019 2018 Net income (loss) from continuing operations 14,742$ 13,464$ 8,361$ 15,603$ 8,696$ 14,652$ 13,695$ 10,010$ Income tax expense (benefit) 3,884 3,299 2,015 3,809 2,423 3,723 3,815 2,558 Income (loss) before taxes 18,626 16,763 10,376 19,412 11,119 18,375 17,510 12,568 Other Expense 1,819 - 7,162 - - - - - Net investment gains/(losses) (275) 2,362 (245) (406) (137) (686) (113) 287 Adjusted operating income before taxes 20,170 19,125 17,293 19,006 10,982 17,689 17,397 12,855 Less: income tax expense on adjusted operating income 4,217 3,468 3,468 3,724 2,423 3,723 3,815 2,558 Adjusted operating income 15,953$ 15,657$ 13,825$ 15,282$ 8,559$ 13,966$ 13,582$ 10,297$ Q4 Q3 Q2 Q1 2019 2018 2017 2016 Net income (loss) from continuing operations 45,494$ 53,729$ (6,904)$ (20,734)$ Income tax expense (benefit) 12,137 13,389 38,233 (23,988) Income (loss) before taxes 57,631 67,118 31,328 (44,722) Other Expense 16,151 - - - Net investment gains/(losses) (770) 1,557 (4,204) 6,147 Adjusted operating income/(loss) before taxes 73,012 68,675 27,124 (38,575) Less: income tax expense on adjusted operating income 15,376 13,389 13,133 (23,988) Adjusted operating income 57,636 55,286 13,991 (14,587) December 31 Unaudited

27 Supplementary Underwriting Information NOTE: Quarterly income statement reported, not audited. 2019 2018 2019 2018 2019 2018 2019 2018 2019 2018 2017 2016 Gross written premiums 249,945$ 221,841$ 227,196$ 201,296$ 235,032$ 222,555$ 255,838$ 249,420$ 968,011$ 895,112$ 836,334$ 771,995$ Net written premiums 222,196 196,171 209,474 179,516 210,568 213,035 209,902 261,352 852,140 850,074 560,286 686,683 Net premiums earned 207,311 193,098 202,455 187,108 202,480 183,123 195,608 167,456 807,854 730,785 609,786 675,778 Net losses and loss adjustment expenses 128,381 113,067 127,196 109,976 127,115 109,933 118,333 101,854 501,025 434,830 393,741 489,464 Catastrophe loss and loss adjustment expenses – 3,560 – – 3,000 – – – 3,000 3,560 8,865 7,938 Unfavorable/(favorable) prior period reserve development 787 (970) 5,495 (1,442) (2,733) (1,335) (395) (1,270) 3,154 (5,071) 20,319 60,082 Underwriting, acquisition and inurance expenses 73,209 70,575 71,920 69,246 71,561 68,133 73,767 63,593 290,457 271,547 213,844 241,873 Policy acquisition expenses 46,712 45,610 45,953 44,195 45,533 43,253 46,573 38,371 184,771 171,429 126,023 152,923 General and administrative expenses 26,497 24,965 25,967 25,051 26,028 24,880 27,194 25,222 105,686 100,118 87,821 88,950 Underwriting Income 5,721$ 9,456$ 3,339$ 7,886$ 3,804$ 5,057$ 3,508$ 2,009$ 16,372$ 24,409$ 2,201$ (55,559)$ Underwriting Ratios Ex-CAT current accident year loss and LAE ratio 61.5% 57.2% 60.1% 59.5% 62.6% 60.8% 60.7% 61.5% 61.2% 59.7% 59.8% 62.4% Catastrophe loss and LAE ratio 0.0% 1.8% 0.0% 0.0% 1.5% 0.0% 0.0% 0.0% 0.4% 0.5% 1.5% 1.2% Unfavorable/(favorable) prior period reserve development ratio 0.4% -0.5% 2.7% -0.8% -1.3% -0.8% -0.2% -0.7% 0.4% -0.7% 3.3% 8.9% Loss and LAE ratio 61.9% 58.6% 62.8% 58.8% 62.8% 60.0% 60.5% 60.8% 62.0% 59.5% 64.6% 72.4% Policy acquisition expense ratio 22.5% 23.6% 22.7% 23.6% 22.5% 23.7% 23.8% 24.0% 22.9% 23.8% 22.5% 22.6% General and adminstrative expense ratio 12.8% 12.9% 12.8% 13.4% 12.8% 13.5% 13.9% 14.0% 13.1% 13.4% 12.6% 13.2% Expense Ratio 35.3% 36.5% 35.5% 37.0% 35.3% 37.2% 37.7% 38.0% 36.0% 37.2% 35.1% 35.8% Combined Ratio 97.2% 95.1% 98.3% 95.8% 98.1% 97.2% 98.2% 98.8% 98.0% 96.7% 99.7% 108.2% Adjusted Underwriting Ratios Ex-CAT current accident year loss and LAE ratio 61.5% 57.3% 59.3% 60.0% 61.6% 60.7% 60.7% 61.5% 61.2% 59.8% 60.6% 63.5% Catastrophe loss and LAE ratio 0.0% 1.8% 0.0% 0.0% 1.5% 0.0% 0.0% 0.0% 0.4% 0.5% 0.0% 0.0% Unfavorable/(favorable) prior period reserve development ratio 0.0% -0.5% 2.7% -0.8% -1.3% -0.8% -0.2% -0.7% -0.2% -0.7% 3.3% 8.9% Adjusted Loss and LAE ratio 61.5% 58.6% 62.0% 59.2% 61.7% 60.0% 60.5% 60.8% 61.4% 59.6% 63.9% 72.4% Policy acquisition expense ratio 22.9% 23.6% 23.5% 23.2% 23.6% 23.8% 23.8% 23.6% 23.5% 23.6% 22.3% 22.6% General and adminstrative expense ratio 12.8% 12.9% 12.8% 13.4% 12.8% 13.5% 13.9% 14.0% 13.1% 13.4% 12.6% 13.2% Adjusted Expense Ratio 35.7% 36.5% 36.3% 36.6% 36.5% 37.3% 37.7% 37.6% 36.6% 37.0% 34.9% 35.8% Adjusted Combined Ratio 97.2% 95.1% 98.3% 95.8% 98.2% 97.3% 98.2% 98.4% 98.0% 96.6% 98.8% 108.2% Three Months Ended December 31 Three Months Ended September 30 Three Months Ended June 30 Three Months Ended March 31 Year Ended December 31 Unaudited

28 Factors Impacting the Results of Operations (WAQS) NOTE: Quarterly income statement reported, not audited. 2019 2018 2019 2018 2019 2018 2019 2018 2019 2018 2017 2016 Gross written premiums –$ –$ –$ –$ –$ –$ –$ –$ –$ –$ –$ –$ Ceded written premiums – (9,888) – (55) 3 18,831 – 49,969 3 58,857 (160,779) – Net written premiums – (9,888) – (55) 3 18,831 – 49,969 3 58,857 (160,779) – Net premiums earned - 40 - (56) 3 (1,368) – (13,176) 3 (14,560) (87,362) – Net losses and LAE 907 (92) 1,632 (874) 2,207 (642) – (7,906) 4,746 (9,514) (51,897) – Underwriting, acquisition and insurance expenses (906) 128 (1,632) 823 (2,205) (624) – (4,282) (4,743) (3,955) (29,560) – Underwriting income (loss) (1) 4 – (5) 1 (102) – (988) – (1,091) (5,905) – Adjustment to loss and LAE ratio -0.4% 0.0% -0.8% 0.4% -1.1% 0.0% 0.0% 0.0% -0.6% 0.1% -0.7% 0.0% Adjustment to expense ratio 0.4% 0.0% 0.8% -0.4% 1.2% 0.1% 0.0% -0.4% 0.6% -0.2% -0.2% 0.0% Adjustment to combined ratio 0.0% 0.0% -0.1% 0.0% 0.1% 0.1% 0.0% -0.4% 0.0% -0.1% -0.9% 0.0% Adjusted loss and LAE ratio 61.5% 58.6% 62.0% 59.2% 61.7% 59.9% 60.5% 60.8% 61.4% 59.6% 63.9% 72.4% Adjusted expense ratio 35.7% 36.5% 36.3% 36.6% 36.4% 37.3% 37.7% 37.6% 36.6% 37.0% 34.9% 35.8% Adjusted combined ratio 97.2% 95.1% 98.3% 95.8% 98.1% 97.2% 98.2% 98.4% 98.0% 96.6% 98.8% 108.2% Three Months Ended December 31 Three Months Ended September 30 Three Months Ended June 30 Three Months Ended March 31 Year Ended December 31 Unaudited

29 Share & Per Share Information NOTE: Quarterly income statement reported, not audited. 2019 2018 2019 2018 2019 2018 2019 2018 2019 2018 2017 2016 Shares Outstanding 43,058 38,851 43,021 38,743 38,851 38,743 38,851 38,743 43,058 38,851 38,743 35,453 Fully Diluted Shares Outstanding 45,197 39,455 45,225 39,441 39,455 39,441 39,455 39,441 45,197 39,455 39,441 36,083 Book Value Per Share (2) 12.61$ 10.03$ 12.33$ 9.90$ 11.81$ 9.52$ 10.99$ 9.44$ 12.61$ 10.03$ 9.70$ 10.74$ Book Value Per Share (Fully Diluted) (2) 12.01$ 9.88$ 11.73$ 9.73$ 11.63$ 9.35$ 10.82$ 9.27$ 12.01$ 9.88$ 9.53$ 10.55$ Tangible Book Value Per Share (2) 11.93$ 9.28$ 11.65$ 9.15$ 11.06$ 8.77$ 10.24$ 8.68$ 11.93$ 9.28$ 8.95$ 9.90$ Tangible Book Value Per Share (Fully Diluted) (2) 11.37$ 9.14$ 11.09$ 8.99$ 10.89$ 9.61$ 10.08$ 8.53$ 11.37$ 9.14$ 8.79$ 9.72$ Weighted Average Basic Shares Outstanding 43,978 38,785 42,642 38,743 38,851 38,743 38,851 38,743 41,095 38,753 37,555 35,376 Weighted Average Diluted Shares Outstanding 44,340 39,447 43,060 39,441 39,455 39,441 39,455 39,441 41,523 39,441 37,555 35,376 Earnings per Share - Basic: Net income from continuing operations 0.34$ 0.35$ 0.20$ 0.40$ 0.22$ 0.38$ 0.35$ 0.26$ 1.11$ 1.39$ (0.18)$ (0.59)$ Adjusted operating income (1) 0.36$ 0.40$ 0.32$ 0.39$ 0.37$ 0.36$ 0.35$ 0.27$ 1.40$ 1.43$ 0.37$ (0.41)$ Earnings per Share - Diluted: Net income from continuing operations 0.33$ 0.34$ 0.19$ 0.40$ 0.22$ 0.37$ 0.35$ 0.25$ 1.10$ 1.36$ (0.18)$ (0.59)$ Adjusted operating income (1) 0.36$ 0.40$ 0.32$ 0.39$ 0.36$ 0.36$ 0.34$ 0.26$ 1.39$ 1.40$ 0.37$ (0.41)$ Adjusted operating return on equity (ROE) (3) 11.9% 16.2% 11.2% 16.2% 12.8% 15.4% 13.3% 11.1% 12.4% 14.4% 3.7% -3.6% Adjusted operating return on tangible equity (ROTE) (3) 12.6% 17.5% 11.9% 17.6% 13.8% 16.5% 14.3% 12.1% 13.2% 15.6% 4.0% -3.8% Year Ended December 31Three Months Ended September 30 Three Months Ended June 30 Three Months Ended March 31Three Months Ended December 31 Unaudited

Gross Written Premium by Segment 30 NOTE: Quarterly reported, not audited. (in $000s) 2019 2018 2019 2018 2019 2018 2019 2018 2019 2018 Customer Segment Construction 34,879$ 29,967$ 27,296$ 22,451$ 32,494$ 26,575$ 23,248$ 22,953 117,918$ 101,946$ Consumer Services 32,801 26,918 35,503 29,874 37,892 28,387 27,485 21,907 133,682 107,086 Marine and Energy 22,811 21,088 26,710 22,040 25,359 22,440 19,192 17,410 94,071 82,978 Media and Entertainment 34,154 32,074 28,702 27,224 32,402 32,251 29,692 28,377 124,950 119,925 Professional Services 33,645 28,292 27,015 24,750 29,104 27,939 29,562 29,565 119,326 110,546 Real Estate 50,720 41,145 41,566 19,477 46,614 44,072 28,735 27,958 167,635 132,652 Transportation 32,828 24,633 29,621 26,233 18,985 19,851 30,757 21,452 112,191 92,169 Sports 7,245 5,011 8,086 4,176 6,898 5,688 7,850 8,714 30,079 23,590 Customer Segment Subtotal 249,084$ 209,129$ 224,498$ 176,226$ 229,750$ 207,201$ 196,521$ 178,337$ 899,853$ 770,893$ Other 862 12,712 2,698 25,071 5,282 15,354 59,317 71,083 68,159 124,219 Total 249,945$ 221,841$ 227,196$ 201,296$ 235,032$ 222,555$ 255,838$ 249,420$ 968,011$ 895,112$ Q4 Q3 Q2 Q1 Year Ended December 31 Unaudited