March 2022 Investor Presentation

EXPERIENCED MANAGEMENT TEAM Ernie Garateix: Chief Executive Officer Has been in his current role since 2020, prior to which he served as Chief Operating Officer since 2014. Before that, he served as Executive Vice President since the company's 2012 founding. Prior to Heritage, Mr. Garateix served as Vice President of Operations at American Integrity Insurance Group. Before that, Mr. Garateix was Associate Vice President of IT at FCCI Insurance Group. Kirk Lusk: Chief Financial Officer Has been in his current role since 2018. Joined Heritage in 2017 via the acquisition of NBIC Holdings, Inc., where Mr. Lusk was also Chief Financial Officer. Before that, Mr. Lusk was International Chief Financial Officer of Aetna, Inc., Chief Financial Officer of Alea Group Holdings Bermuda Ltd. and Chief Financial Officer of GE ERC Global Casualty and GE Capital Auto Warranty Services. Tim Moura: President, NBIC Has been in his current role since 2017, prior to which he served as SVP of Marketing, Agency, and Client Services since 2014. Prior to NBIC, Mr. Moura served as Vice President of Business Development and Commercial Lines for Tower Group Companies. was Vice Before that, Mr. Moura President, Underwriting and Product Management, Personal Lines, at OneBeacon Insurance Group. March 2022 Investor Presentation Tim Johns: President, Zephyr Has been in his current role since 2018. Prior to Zephyr, Mr. Johns was Chief Consumer Officer at the Hawaii Medical Service Association, the largest health insurer in Hawaii. Before that, Mr. Johns held multiple executive leadership roles within private, public and non-profit enterprises in Hawaii. 7 Randy Jones: President, Commercial Division Has been in his current role since 2014. Prior to Heritage, Mr. Jones was SVP of American Strategic Insurance's (ASI) commercial division. Before that, Mr. Jones served in management at other insurance enterprises. Mr. Jones holds the American Risk Manager (ARM) and Certified Property Insurance Adviser (CPIA) designations. H

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