FOXOD · Foxo Technologies Inc.

Represents shares sold by KR8 ai Inc., of which the Reporting Person is an officer, director and shareholder.

Gives no effect to shares which may be issued to KR8 ai Inc. as consideration for rights granted and services to be rendered pursuant to the Master Software and Services Agreement between KR8 ai Inc. and the issuer.

Represents shares sold by KR8 ai Inc., of which the Reporting Person is an officer, director and shareholder.

Gives no effect to shares which may be granted to KR8 ai Inc. as consideration for rights granted and services to be rendered pursuant to the Master Software and Services Agreement between KR8 ai Inc. and the issuer.

Represents shares issued to KR8 ai Inc., of which the Reporting Person is an officer, director and shareholder as consideration for rights granted and services to be rendered pursuant to the Master Software and Services Agreement between KR8 ai Inc. and the issuer.

Represents shares issued to KR8 ai Inc., of which the Reporting Person is an officer, director and shareholder as consideration for rights granted and services to be rendered pursuant to the Master Software and Services Agreement between KR8 ai Inc. and the issuer.

Gift rescinded by mutual agreement.

Shares previously gifted then gift rescinded.

Gift rescinded by mutual agreement.

Shares previously gifted then gift rescinded.

As compensation for services rendered and to be rendered as an officer of the issuer, the reporting person was granted Class A Common Stock under the FOXO Technologies Inc. 2022 Equity Incentive Plan

As compensation for services rendered and to be rendered as an officer and director of the issuer, the reporting person was granted Class A Common Stock under the FOXO Technologies Inc. 2022 Equity Incentive Plan.

4,647,405 shares of Class A Common Stock are held by Baboon Partners, LLC. Mr. Dowling is the manager and exercises control of Baboon Partners, LLC. Does not include shares of Class A Common Stock held by Coat Tail Partners, LLC for which Mr. Dowling is no longer a manager and does not exercise any control.

In connection with the Merger (as defined below), the reporting person received a restricted share award equal to 760,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing Date (as defined below) if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.

In connection with the merger described in that certain Agreement and Plan of Merger, dated as of 2/24/2022 (as amended, the "Merger Agreement"), by and among FOXO Technologies Inc., formerly Delwinds Insurance Acquisition Corp. (the "Issuer"), DWIN Merger Sub Inc. ("Merger Sub"), and FOXO Technologies Operating Company, formerly FOXO Technologies Inc. ("FOXO"), pursuant to which Merger Sub merged with and into FOXO, with FOXO surviving as a wholly-owned subsidiary of the Issuer (the "Merger"). Pursuant to the terms and conditions of the Merger Agreement, in connection with the closing of the Merger on 9/15/2022 (the "Closing Date"), the reporting person received 17,425 shares of Class A common stock in the Issuer.

Represents the receipt for no consideration from the distribution by DIAC Sponsor LLC (the "Sponsor") to its members of (i) 632,500 shares of Class A common stock of Delwinds, (ii) 4,431,250 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

Upon the closing of the business combination of Delwinds with FOXO Technologies Operating Company ("FOXO"), (i) all shares of outstanding Class B shares of Delwinds were converted into shares of Class A shares of Delwinds, and (ii) Delwinds effected a name change to FOXO Technologies Inc.

The stock options were received in exchange for stock options to purchase 69,500 shares of Class A common stock of FOXO Technologies Operating Company ("FOXO") in connection with the merger of FOXO with and into a wholly owned subsidiary of the Issuer (the "Merger"), which closed on 9/15/2022 (the "Closing Date"). As of the Closing Date, 7,849.35 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.

In connection with the Merger (as defined below), the reporting person received a restricted share award equal to 510,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing Date (as defined below) if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.

The stock options were received in exchange for stock options to purchase 5 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 0.39 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.

In connection with the Merger (as defined below), the reporting person received a restricted share award equal to 130,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing Date (as defined below) if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.

The stock option was received in exchange for a stock option to purchase 7,713 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 1,617.78 of the shares of Class A common stock of the Issuer subject to the stock optionss were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 8/9/2024.

Represents the receipt for no consideration from the distribution by DIAC Sponsor LLC (the "Sponsor") to its members of (i) 632,500 shares of Class A common stock of Delwinds, (ii) 4,431,250 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

Upon the closing of the business combination of Delwinds with FOXO Technologies Operating Company ("FOXO"), (i) all shares of outstanding Class B shares of Delwinds were converted into shares of Class A shares of Delwinds, and (ii) Delwinds effected a name change to FOXO Technologies Inc.

Shares are held of record by Mr. Andrew Poole as custodian for a minor child under the LA Gifts to Minors Act. Mr. Poole disclaims beneficial ownership of these shares, and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of these securities for purposes of Section 16 or for any other purpose.

In connection with the Merger (as defined below), the reporting person received a restricted share award equal to 760,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing Date (as defined below) if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.

The stock options were received in exchange for stock options to purchase 6,421 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 1,36.57 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 8/9/2024.

In connection with the Merger (as defined below), the reporting person received a restricted share award equal to 760,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.

The stock options were received in exchange for stock options to purchase 90,000 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 32,913.65 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments over the following thirty-six (36) months until fully vested on 12/31/2023.

The stock options were received in exchange for stock options to purchase 6,148 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 1,289.54 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 8/9/2024.

The stock option was received in exchange for a stock option to purchase 1,157,405 shares of Class A common stock of FOXO Technologies Operating Company ("FOXO") in connection with the merger of FOXO with and into a wholly owned subsidiary of the Issuer (the "Merger"), which closed on 9/15/2022 (the "Closing Date"). As of the Closing Date, 667,085.48 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 12/31/2023.

The stock option was received in exchange for a stock option to purchase 5 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 0.39 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.

In connection with the Merger, the reporting person received a restricted share award equal to 3,507,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.

In connection with the merger described in that certain Agreement and Plan of Merger, dated as of 2/24/2022 (as amended, the "Merger Agreement"), by and among FOXO Technologies Inc., formerly Delwinds Insurance Acquisition Corp. (the "Issuer"), DWIN Merger Sub Inc. ("Merger Sub"), and FOXO Technologies Operating Company, formerly FOXO Technologies Inc. ("FOXO"), pursuant to which Merger Sub merged with and into FOXO, with FOXO surviving as a wholly-owned subsidiary of the Issuer (the "Merger"). Pursuant to the terms and conditions of the Merger Agreement, in connection with the closing of the Merger on 9/15/2022 (the "Closing Date"), the reporting person received (i) 372,680 shares of Class A common stock in the Issuer to be held by JK-JBM Family Investment LLC and (ii) 1,161,674 shares of Class A common stock in the Issuer to be held by FOXO Management, LLC.

Securities held of record by JK-JBM Family Investment LLC (the "LLC"). Jon Sabes is the manager of the LLC and is deemed to have sole voting and investment power over the securities held by the LLC.

Represents the distribution for no consideration by DIAC Sponsor LLC (the "Sponsor") of (i) 4,431,250 shares of Class A common stock of Delwinds, (ii) 632,500 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

Represents the forfeiture, for no consideration, by the Sponsor 600,000 shares of Class B common stock of Delwinds.

As a managing member of the Sponsor, Mr. Andrew Poole may be deemed to share beneficial ownership of shares of Delwinds common stock held directly by the Sponsor, and disclaims any beneficial ownership of the reported shares other than to the extent of any pecuniary interest he may have therein, directly or indirectly.

Represents the distribution for no consideration by DIAC Sponsor LLC (the "Sponsor") of (i) 4,431,250 shares of Class A common stock of Delwinds, (ii) 632,500 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

As a managing member of the Sponsor, Mr. Andrew Poole may be deemed to share beneficial ownership of shares of Delwinds common stock held directly by the Sponsor, and disclaims any beneficial ownership of the reported shares other than to the extent of any pecuniary interest he may have therein, directly or indirectly.

Represents the distribution for no consideration by DIAC Sponsor LLC (the "Sponsor") of (i) 4,431,250 shares of Class A common stock of Delwinds, (ii) 632,500 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

As a managing member of the Sponsor, Mr. Andrew Poole may be deemed to share beneficial ownership of shares of Delwinds common stock held directly by the Sponsor, and disclaims any beneficial ownership of the reported shares other than to the extent of any pecuniary interest he may have therein, directly or indirectly.

The stock options were received in exchange for stock options to purchase 30,000 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 3,388.2 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 2/8/2025.

Securities held of record by FOXO Management, LLC ("FOXO Management"). Jon Sabes, is the sole voting member of FOXO Management and is deemed to have sole voting and investment power over the securities held by FOXO Management.

The warrant was received in exchange for a warrant to purchase 312,500 shares of FOXO Class A common stock in connection with the Merger. The warrant is immediately exercisable.

Securities held of record by JK-JBM Family Investment LLC (the "LLC"). Jon Sabes is the manager of the LLC and is deemed to have sole voting and investment power over the securities held by the LLC.

The stock options were received in exchange for stock options to purchase 5 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 0.39 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.

The stock options were received in exchange for stock options to purchase 135,000 shares of Class A common stock of FOXO Technologies Operating Company ("FOXO") in connection with the merger of FOXO with and into a wholly owned subsidiary of the Issuer (the "Merger"), which closed on 9/15/2022 (the "Closing Date"). As of the Closing Date, 43,562.78 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 12/31/2023.

The stock options were received in exchange for stock options to purchase 5 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 0.39 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.

Represents the receipt for no consideration from the distribution by DIAC Sponsor LLC (the "Sponsor") to its members of (i) 632,500 shares of Class A common stock of Delwinds, (ii) 4,431,250 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

Upon the closing of the business combination of Delwinds with FOXO Technologies Operating Company ("FOXO"), (i) all shares of outstanding Class B shares of Delwinds were converted into shares of Class A shares of Delwinds, and (ii) Delwinds effected a name change to FOXO Technologies Inc.

Represents the receipt for no consideration from the distribution by DIAC Sponsor LLC (the "Sponsor") to its members of (i) 632,500 shares of Class A common stock of Delwinds, (ii) 4,431,250 shares of Class B common stock of Delwinds, and (iii) 316,250 warrants to purchase shares of Class A common stock to its members (the "Sponsor Distribution"). Andrew J. Poole received (i) 85,000 shares of Class A common stock; (ii) 1,041,662 shares of Class A common stock underlying shares of Class B common stock; and (iii) 42,500 shares of Class A common stock underlying warrants.

Upon the closing of the business combination of Delwinds with FOXO Technologies Operating Company ("FOXO"), (i) all shares of outstanding Class B shares of Delwinds were converted into shares of Class A shares of Delwinds, and (ii) Delwinds effected a name change to FOXO Technologies Inc.

Shares are held of record by Mr. Andrew Poole as custodian for a minor child under the Texas Uniform Transfers to Minors Act. Mr. Poole disclaims beneficial ownership of these shares, and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of these securities for purposes of Section 16 or for any other purpose.

The stock options were received in exchange for stock options to purchase 5 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 0.39 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.