X0306 4 2021-08-04 0 0001828105 Hippo Holdings Inc. HIPO 0001294172 McCathron Richard C/O HIPPO HOLDINGS INC. 150 FOREST AVENUE PALO ALTO CA 94301 1 1 0 0 President Common Stock 2021-08-04 4 A 0 3008506 A 3008506 D Common Stock 2021-08-04 4 D 0 500000 D 2508506 D Stock Option (Right to Buy) 0.04 2021-08-04 4 A 0 86929 A 2027-02-28 Common Stock 86929 86929 D Stock Option (Right to Buy) 0.16 2021-08-04 4 A 0 163594 A 2028-01-23 Common Stock 163594 163594 D Stock Option (Right to Buy) 0.33 2021-08-04 4 A 0 362209 A 2029-01-22 Common Stock 362209 362209 D Stock Option (Right to Buy) 0.33 2021-08-04 4 A 0 507666 A 2029-05-14 Common Stock 507666 507666 D Stock Option (Right to Buy) 1.06 2021-08-04 4 A 0 695433 A 2030-09-27 Common Stock 695433 695433 D Pursuant to the business combination of Hippo Holdings Inc. (the "Issuer") and Hippo Enterprises Inc. ("Old Hippo"), each share of Old Hippo outstanding common stock was automatically converted into the right to shares of the Issuer's Common Stock based on a 1 to 6.95433 conversion ratio ("Conversion Ratio"). In addition, each outstanding Old Hippo equity award was automatically converted into a corresponding equity award of the Issuer based on the Conversion Ratio and with the same terms and vesting conditions as the Old Hippo equity awards. Shares redeemed by the Issuer at a price per share of $10 in a transaction exempt pursuant to Rule 16b-3(e). This option is fully vested and exercisable. 1/16th of the shares underlying the option vest on each quarterly anniversary measured from January 23, 2018, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date. 1/48th of the shares underlying the option vest on each monthly anniversary measured from January 23, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date. 1/48th of the shares underlying the option vest on each monthly anniversary measured from May 13, 2019, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date. 1/48th of the shares underlying the option vest on each monthly anniversary measured from August 27, 2020, subject to the Reporting Person continuing to provide services to the Issuer through the applicable vesting date. /s/ Stewart Ellis, as Attorney-in-Fact for Richard McCathron 2021-08-04