March 2022 Investor Presentation

STRATEGIC INSURTECH PARTNERSHIP Entered into a strategic partnership with Slide, a startup InsurTech P&C carrier, providing Heritage with enhanced technological capabilities and allowing for participation in the InsurTech sector's upside. Partnership provides Heritage with the opportunity to: Leverage Slide's InsurTech capabilities to improve underwriting and rating decisions. Further capitalize on strong agency relationships by generating commission income on policies that don't meet Heritage's underwriting criteria (e.g., due to geographic concentration). Participate in the InsurTech sector without potentially significant capital requirements to develop similar capabilities internally. Based on current publicly traded InsurTech valuations, potential to generate a meaningful capital gain, which, if realized, could provide additional funds for share buybacks or debt retirement. Terms of the partnership Heritage will receive: Approximately 6% equity stake in Slide, an InsurTech P&C carrier with an estimated $250 million post-money valuation, and warrants allowing it to purchase an additional equity interest at Slide's pre-money valuation. Slide will be accounted for as an equity investment. Perpetual, royalty free license to certain aspects of Slide's software. Heritage will: Transfer ownership (subject to regulatory approval) of Pawtucket (Heritage will retain Pawtucket's surplus), a dormant P&C carrier licensed in Rhode Island. Transfer ownership of First Access Insurance Group, a Florida-licensed MGA with minimal earnings. Provide access to historical claims and underwriting data. March 2022 Investor Presentation 16 H

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