SKWD Investor Presentation – March 2024

INVESTOR PRESENTATION

MARCH 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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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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MAGNET FOR TOP TALENT

• 45% of our 134 new hires in 2023 were from employee referrals

• 7% Voluntary Turnover

• Our latest engagement survey revealed:

• 95% of employees agreed/strongly agreed

with the statements "I am proud to work for this organization" and "I understand the importance of how my role impacts company success"

• Overall net promoter score (positive responses minus negative responses) of over 80%

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