Bowhead Investor Presentation February 2025

Our key investment highlights

Focused on profitable, growing lines in attractive E&S market

Strong underwriting culture with fully-integrated and accountable value chain

Ability to deliver differentiated profitability across market cycles

Deep, long-standing distribution relationships based on expertise, service and mutual benefit

Highly experienced and entrepreneurial management team

Clean balance sheet with no reserves from accident years prior to 2020

Commitment to long-term value generates strong returns, making us well-positioned for continued growth

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Bowhead: Who we are

Growing and profitable E&S focused specialty P&C business founded and led by industry veteran, Stephen Sills, and supported through a strategic partnership with American Family Mutual Insurance Company, S.I. ("AmFam")

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Bowhead: By the numbers

Note: 1 Year ended December 31, 2024; 2 Combined ratio for year ended December 31, 2024 was comprised of a 64.4% loss ratio and a 31.4% expense ratio. The loss ratio is based on loss picks informed by industry data rather than only using internal data from our limited operating history. Movement in the loss ratio from last year reflects mix changes in our portfolio, where Casualty, which has higher current accident year industry loss ratios, comprised a larger proportion of the Company's gross written premiums-62.1% in 2024 compared to 54.7% in 2023. There was no prior accident year reserve development in our loss ratio for the year. The expense ratio reflects continued scaling of our business and prudent management of operating expenses; 3 2024 adjusted ROE is calculated as adjusted net income divided by the average of mezzanine and stockholders' equity as of December 31, 2023 and December 31, 2024. Adjusted ROE was impacted by the $178.4 million increase in mezzanine equity and stockholders' equity, mainly due to the $131.0 million of net proceeds received from the IPO and $38.2 million of net income generated during the year, and a $7.3 million reduction in after tax net income as a result of the costs related to the IPO and secondary offering. Adjusted ROE and adjusted net income are Non-GAAP financial measures. See "Non-GAAP Reconciliation" on slide 18 for a reconciliation of the non-GAAP financial measure to the most directly comparable U.S. GAAP measure; 4 Leadership team includes Stephen Sills, David Newman, Derek Broaddus, Daniel Gamble, Joe Calcagno and Brandon Mezick.

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Highly experienced and entrepreneurial management team

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Focused on profitable, growing lines in attractive E&S market

Expanding Commercial E&S Market ($Bn)

Source: S&P Global; Note: E&S premiums sourced per S&P Global based on license types in Schedule T of statutory filings

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Focused on profitable, growing lines in attractive E&S market (cont'd)

E&S premiums1 as % of 2023 GAAP GWP

Source: S&P Global; Note: 1 Represents 2023 statutory direct written premiums; 2 Markel U.S. GAAP GWP includes program services and fronting; 3 For the year ended December 31, 2023; 4 Represents Other Liability: Occurrence, Other Liability: Claims Made and Medical

Professional Liability: Claims Made

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Strong underwriting culture with fully-integrated and accountable value chain

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Ability to deliver differentiated profitability across market cycles

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