Skyward Specialty Insurance : SKWD Investor Presentation – May 2024

INVESTOR PRESENTATION

MAY 2024

LEGAL DISCLAIMERS

Forward-Looking Statements

This presentation may contain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. The words "believe," "may," "will," "intend," "expect," "anticipate," "estimate," "target," and similar expressions, or the negative thereof, among others, identify forward-looking statements. All forward-looking statements are based on assumptions, expectations and other information currently available to management. Although SKWD believes that the expectations reflected in forward-looking statements have a reasonable basis, it can give no assurance that these expectations will prove to be correct. Such forward-looking statements are subject to certain risks and uncertainties that could cause the Company's actual results to differ materially from those projected, anticipated or implied. The most significant of these risks and uncertainties are described in SKWD's most recently filed Annual Report on Form 10-K and its other filings with the Securities and Exchange Commission, and include (but are not limited to) legislative changes at both the state and federal level, state and federal regulatory rule making promulgations and adjudications, class action litigation involving the insurance industry and judicial decisions affecting claims, policy coverages and the general costs of doing business, the potential loss of key members of our management team or key employees and our ability to attract and retain personnel, the impact of competition on products and pricing, inflation in the costs of the products and services insurance pays for, product development, geographic spread of risk, weather and weather-related events, other types of catastrophic events, our ability to obtain reinsurance coverage at prices and on terms that allow us to transfer risk and adequately protect our company against financial loss, and losses resulting from reinsurance counterparties failing to pay us on reinsurance claims. Except to the extent required by law, SWKD undertakes no obligation to update or revise any forward-looking statements.

Non-GAAP Financial Measures

In addition to financial information presented in accordance with U.S. generally accepted accounting principles ("GAAP"), this presentation includes certain non-GAAP financial measures. These non-GAAP measures are presented for supplemental informational purposes only and should not be considered a substitute for financial information presented in accordance with GAAP. These non-GAAP measures have limitations as analytical tools, and they should not be considered in isolation or as a substitute for analysis of other GAAP financial measures. A reconciliation of these measures to the most directly comparable GAAP measures is included in the Appendix to this presentation. This presentation contains statistical data, estimates, and forecasts that are based on independent industry publications or other publicly available information, as well as other information based on our internal sources. This information involves many assumptions and limitations, and you are cautioned not to give undue weight to these estimates. We have not independently verified the accuracy or completeness of the data contained in these industry publications and other publicly available information. Accordingly, we make no representations as to the accuracy or completeness of that data nor do we undertake to update such data after the date of this presentation.

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SELECT MARKET INFORMATION

As of March 31, 2024
Ticker Symbol	SKWD
Exchange	NASDAQ Global Select Market
Stock Price	$37.41
Market Capitalization	$1.4 billion
Book Value (per share)	$17.44
Debt to Total Capitalization Ratio	14.7%
Full-time Employees	528

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WE ARE A DISTINCTIVE SPECIALTY P&C INSURER

Skyward Specialty is a rapidly growing specialty insurance company, delivering commercial P&C products and solutions on a non-admitted and admitted basis. The Company operates through eight underwriting divisions -Accident & Health, Captives, Global Property & Agriculture, Industry Solutions, Professional Lines, Programs, Surety and Transactional E&S. All of our insurance company subsidiaries are group rated and have a financial strength rating of "A-" (Excellent) with positive outlook from A.M. Best Company.

We approach insurance differently. Our specialty insurance experts dig deeper to customize solutions to help brokers and agents deliver impactful solutions to their clients. We operate at the complex end of the specialty market and leverage technology to bring unique, innovative insurance solutions to market.

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WE ARE MISSION & VALUES LED

OUR MISSON

to spark potential by smartly shifting risk to a safer place

OUR VISION

to be the specialty insurance company where great people want to work, the best partners and customers bring their business and top-tier performance ensues

OUR VALUES

Grow personally and professionally

We are committed to bettering ourselves and each other, and we have fun doing it.

Rise above the usual

We go farther to gain the insight it takes to find better answers and create the right solutions

Engage in inclusion

We avidly seek a rich diversity of thought, backgrounds and perspectives

Act in good faith

We are transparent, honest and accountable to ourselves and each other, no matter what

Transcend the self

We are high achieving individuals who are humble enough to know that teamwork takes us even higher

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HIGHLY EXPERIENCED LEADERSHIP TEAM

					Andrew Robinson	Mark Haushill
					Chief Executive Officer	Chief Financial Officer
Joined Skyward in 2020	Joined Skyward in 2015
30+ Years of Experience	30+ Years of Experience

			Sandip Kapadia	Tom Schmitt
			EVP, Chief Actuary &	Chief Administrative Officer
			Analytics Officer	& Chief People Officer
Joined Skyward in 2020	Joined Skyward in 2020
20+ Years of Experience	30+ Years of Experience

	John Burkhart	Kirby Hill	Sean Duffy
	President, Specialty Lines	President, Industry Solutions,	Chief Claims Officer
		Programs & Captives
Joined Skyward in 2021	Joined Skyward in 2010	Joined Skyward in 2019
30+ Years of Experience	30+ Years of Experience	25+ Years of Experience

Dan Bodnar	Doug Davies		Leslie Shaunty
Chief Information &	Senior Vice President,		General Counsel
Technology Officer	Global Property Division
Joined Skyward in 2017	Joined Skyward in 2013	Joined Skyward in 2013
20+ Years of Experience	20+ Years of Experience	25+ Years of Experience

insureCIO

Experienced and entrepreneurial leadership with proven track record to build and lead top-tier organizations

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RULE OUR NICHE STRATEGY

Focused on creating a competitive moat, winning in chosen niches, and delivering top quartile performance

Target Business

• Underserved "Niche" Markets with Insufficient Coverage
• Complex Risks

Differentiating Factors

• Customized Products & Solutions
• Exceptional Underwriting & Claims Talent

• Advanced Technology & Analytics

• Responsiveness to Market Opportunities and Dislocation

Outcome

• Top Quartile Performance
• Strong Defensible Market Position

• Competitive Moat

• Low Underwriting Volatility

Target

Business

Differentiating

Factors

Outcome

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OUR UNDERWRITING SUCCESS

EIGHT UNDERWRITING DIVISIONS(1)

We operate through eight underwriting divisions, each of which are now producing more than $100 million. Each division is now at a scale that can sustainably contribute to the Company's earnings.

Industry Solutions

Global Property & Agriculture		20%
	7%
Programs	9%
Captive
	3/31/24 GWP:	19%
Professional Lines	10%	$1,558M
Accident & Health
Transactional E&S		11%	12%
Surety		12%

(1) Data for continuing business for the twelve months ended March 31, 2024.

BALANCED BUSINESS MIX(1)

Our balanced portfolio strengthens our market position and stabilizes our revenue streams, demonstrating our commitment to sustainable, long-term growth within the industry.

BY 46%

54% DURATION

SHORT-TAIL

MEDIUM-TAIL

44% BY

MARKET 56%

NON-ADMITTED

ADMITTED

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WE ARE TECHNOLOGY POWERED

Technology and Analytics

Core Operating Platform

Flexible platform designed to accelerate speed to

market and enhance scalability in a

cost-efficient manner

Superior Business Intelligence Platform

Foundation for reporting, business intelligence,

analytics and advanced data capabilities

Predictive Analytics

Use of predictive analytics including artificial

intelligence for superior risk selection, pricing and

claims handling

SkyBI Provides Us with Real Time Intelligence

Overview	• Single, comprehensive enterprise-wide repository that provides real-
time intelligence in an easy to consume visualized format
Overview

	•	Powered by multiple data sources: production data, pricing /
		retention metrics, claims data, actuarial and select third-party data
Behind SkyBI	•	Data can be filtered by distributor, customer segment, LOB, industry,
	underwriting segmentation and specific-risk feature among others

	• Enables high level business review and in-depth analyses
Impact on	•	Daily and monthly updates allow for a quicker response time
•	Better risk selection, improved pricing and stronger claims outcomes
Decision Making

Advanced technology and data analytics amplify our underwriting and claims capabilities

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INDUSTRY RECOGNITION OF OUR TALENT & TECHNOLOGY LEADERSHIP

ORBIE Awards

Houston CIO - Large Corporate

Business Insurance

Best Places to Work in Insurance 2023

Elite 50 Internships 2022 Winner

Elite 50 Internships 2023 Winner

5- Star Winner 2023 - Professional Liability Provider by Insurance Business America

Datos Insights, formerly AiteNovarica,

Impact Award winner 2023

SkyVUE Underwriting Workbench

Insurance Marketing and Communications Assoc. Showcase Winner 2023 - Silver Award

Captive Review

Professional of the Year 2022 Nominee

Professional of the Year 2023 Nominee

2021 Property Casualty 360

Insurance Innovator

SkyDrive Technology

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