HIPO · Hippo Holdings Inc. · Insider Trading

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

This transaction was executed in multiple trades at prices ranging from $35.00 to $35.07. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Includes 34,199 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 276,190 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 276,190 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

Includes 34,199 RSUs.

Includes 39,561 RSUs.

Includes 81,213 RSUs.

Includes 34,199 RSUs.

Includes 276,190 RSUs.

Represents shares acquired upon vesting of restricted stock units originally granted in connection with the Reporting Person's prior employment with the Issuer.

Includes 15,518 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 296,227 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated June 18, 2025.

Includes 88,578 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 296,227 RSUs.

Includes 43,749 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 296,227 RSUs.

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,820 RSUs.

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date. The Reporting Person has elected to defer settlement of the RSUs until the earliest to occur of (a) a Change in Control of the Issuer, (b) the Reporting Person's separation from service, or (c) the Reporting Person's death. Shares of Common Stock will be delivered to the Reporting Person upon settlement of the RSUs.

Includes 4,808 RSUs.

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Vesting/settlement of 2,502 RSUs originally granted on Oct 1, 2025 into Common Stock

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Vesting/settlement of 4,738 RSUs originally granted on June 3, 2025 into Common Stock

Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

Includes 4,808 RSUs.

Vesting/settlement of 2,502 RSUs originally granted on Oct 1, 2025 into Common Stock

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

This transaction was executed in multiple trades at prices ranging from $25.94 to $26.47. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Includes 37,430 RSUs.

Includes 37,430 RSUs.

Includes 88,578 RSUs.

Includes 296,227 RSUs.

Acquired pursuant to Issuer's Employee Stock Purchase Plan.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 340,418 RSUs.

Includes 109,858 RSUs.

Includes 54,161 RSUs.

Includes 63,661 RSUs.

Includes 340,418 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 343,868 RSUs.

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

Includes 343,868 RSUs.

1/12th of the RSU shares shall vest on each quarterly anniversary of February 15, 2026 over 3 years.

The reported RSUs represent performance-based awards granted on March 3, 2026, subject to service and performance conditions. The award consists of (i) 50% based on relative total shareholder return over a three-year performance period (vesting after three years), (ii) 25% based on gross written premium measured over a one-year performance period (vesting upon achievement), and (iii) 25% based on adjusted return on equity measured over a one-year performance period, subject to an additional one-year service requirement prior to vesting.

Includes 343,868 RSUs.

The reported RSUs represent performance-based awards granted March 2, 2026, subject to service and performance conditions. The award consists of (i) 50% based on relative total shareholder return over a three-year performance period (vesting after three years), (ii) 25% based on gross written premium measured over a one-year performance period (vesting upon achievement), and (iii) 25% based on adjusted return on equity measured over a one-year performance period, subject to an additional one-year service requirement prior to vesting.

Includes 56,186 RSUs.

1/12th of the RSU shares shall vest on each quarterly anniversary of February 15, 2026 over 3 years.