SKWD

SEC source: 0001415889-24-000313 · form4-01032024_090120.xml · nonDerivative · entry 1

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,132

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

SEC source: 0001415889-24-000315 · form4-01032024_090102.xml · derivative · entry 3

Robinson Andrew S · CIK 0001415833 · Director · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 40,137 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F2 · derivative.exercise_date: On January 1, 2021, the reporting person was granted 40,137 RSUs. This award fully vested on January 1, 2024.

F2 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 40,137 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000315 · form4-01032024_090102.xml · nonDerivative · entry 2

Robinson Andrew S · CIK 0001415833 · Director · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 173,631

SEC source: 0001415889-24-000315 · form4-01032024_090102.xml · nonDerivative · entry 1

Robinson Andrew S · CIK 0001415833 · Director · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 189,681

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

SEC source: 0001415889-24-000312 · form4-01032024_090122.xml · derivative · entry 3

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 6,337 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F3 · derivative.exercise_date: On January 1, 2021, the reporting person was granted 6,337 RSUs. This award fully vested on January 1, 2024.

F3 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 6,337 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000312 · form4-01032024_090122.xml · nonDerivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 296,688

SEC source: 0001415889-24-000312 · form4-01032024_090122.xml · nonDerivative · entry 1

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 299,121

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F2 · balance_after: The number of securities reported reflects the November 30, 2023 acquisition of 530 shares of the Company's common stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of June 1, 2023 through November 30, 2023.

SEC source: 0001415889-24-000319 · form4-01032024_090120.xml · derivative · entry 2

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,112 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F3 · derivative.exercise_date: On January 1, 2021, the reporting person was granted 2,112 RSUs. This award fully vested on January 1, 2024.

F3 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 2,112 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000319 · form4-01032024_090120.xml · nonDerivative · entry 1

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,502

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F2 · balance_after: The number of securities reported reflects the November 30, 2023 acquisition of 530 shares of the Company's common stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of June 1, 2023 through November 30, 2023.

SEC source: 0001415889-24-000316 · form4-01032024_090155.xml · derivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CHIEF PEOPLE & ADMIN. OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,281 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F3 · derivative.exercise_date: On January 1, 2021, the reporting person was granted 5,281 RSUs. This award fully vested on January 1, 2024.

F3 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 5,281 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000316 · form4-01032024_090155.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CHIEF PEOPLE & ADMIN. OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,376

SEC source: 0001415889-24-000316 · form4-01032024_090155.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CHIEF PEOPLE & ADMIN. OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,610

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F2 · balance_after: The number of securities reported reflects the November 30, 2023 acquisition of 530 shares of the Company's common stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of June 1, 2023 through November 30, 2023.

SEC source: 0001415889-24-000314 · form4-01032024_090147.xml · derivative · entry 4

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 3,968 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F4 · derivative.exercise_date: On November 5, 2021, the reporting person was granted 3,968 RSUs. This award fully vested on January 1, 2024.

F4 · derivative.expiration_date: On November 5, 2021, the reporting person was granted 3,968 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000314 · form4-01032024_090147.xml · derivative · entry 3

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 1,394 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F3 · derivative.exercise_date: On January 1, 2021, the reporting person was granted 1,394 RSUs. This award fully vested on January 1, 2024.

F3 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 1,394 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000314 · form4-01032024_090147.xml · nonDerivative · entry 2

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,140

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

SEC source: 0001415889-24-000314 · form4-01032024_090147.xml · nonDerivative · entry 1

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,172

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F2 · balance_after: The number of securities reported reflects the November 30, 2023 acquisition of 530 shares of the Company's common stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of June 1, 2023 through November 30, 2023.

SEC source: 0001415889-24-000309 · form4-01032024_090120.xml · derivative · entry 2

Burkhart John A III · CIK 0001936023 · PRESIDENT - SPECIALTY LINES

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,633 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F3 · derivative.exercise_date: On January 1, 2021, the reporting person was granted 5,633 RSUs. This award fully vested on January 1, 2024.

F3 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 5,633 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000309 · form4-01032024_090120.xml · nonDerivative · entry 1

Burkhart John A III · CIK 0001936023 · PRESIDENT - SPECIALTY LINES

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,228

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit ("RSU") represents the right to receive, at settlement, one share of common stock of the issuer. This transaction represents the settlement of RSUs in shares of common stock on their scheduled vesting date.

F2 · balance_after: The number of securities reported reflects the November 30, 2023 acquisition of 530 shares of the Company's common stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of June 1, 2023 through November 30, 2023.

SEC source: 0001415889-23-016524 · form4-12152023_091246.xml · nonDerivative · entry 1

Morrissey Michael J. · CIK 0001432033 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 740

F1 · shares: On December 14, 2023, the reporting person was granted a Restricted Stock Award in the amount of 740 shares of common stock. This award will fully vest on December 14, 2024.

F1 · price: On December 14, 2023, the reporting person was granted a Restricted Stock Award in the amount of 740 shares of common stock. This award will fully vest on December 14, 2024.

SEC source: 0001415889-23-015299 · form4-11202023_091131.xml · nonDerivative · entry 1

WESTAIM Corp · CIK 0001108828 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,979,639

SEC source: 0001415889-23-012305 · form4-08162023_030849.xml · nonDerivative · entry 1

Ashe Gena L · CIK 0001669943 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,734

F1 · shares: On August 14, 2023, the reporting person was granted a Restricted Stock Award in the amount of 1,734 shares of common stock. This award will fully vest on August 14, 2024.

F1 · price: On August 14, 2023, the reporting person was granted a Restricted Stock Award in the amount of 1,734 shares of common stock. This award will fully vest on August 14, 2024.

SEC source: 0001415889-23-012192 · form4-08142023_070836.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,026

F1 · price: The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $25.05 to $25.099, inclusive. The reporting person undertakes to provide to Skyward Specialty Insurance Group, Inc., any security holder of Skyward Specialty Insurance Group, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth.

SEC source: 0001415889-23-011956 · form4-08092023_010843.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,026

F1 · shares: On August 7, 2023, the reporting person was granted a Restricted Stock Award in the amount of 1,724 shares. Each share is equivalent to one share of the Company's common stock. This award fully vests on August 7, 2024.

F1 · price: On August 7, 2023, the reporting person was granted a Restricted Stock Award in the amount of 1,724 shares. Each share is equivalent to one share of the Company's common stock. This award fully vests on August 7, 2024.

SEC source: 0001104659-23-092755 · tm2323993-2_4seq1.xml · nonDerivative · entry 1

WESTAIM CORP · CIK 0001108828 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,579,639

F1 · shares: Shares were acquired from Westaim HIIG Limited Partnership (the "Partnership") in connection with and upon the dissolution of the Partnership.

SEC source: 0001104659-23-092754 · tm2323993-1_4seq1.xml · nonDerivative · entry 1

Westaim HIIG Limited Partnership · CIK 0001616505 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F1 · shares: All shares were distributed to the limited partners of the Reporting Entity in connection with and upon the dissolution of the Reporting Entity.

SEC source: 0001415889-23-010457 · form4-06302023_080615.xml · nonDerivative · entry 1

Hays James Charles · CIK 0001757909 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 27,618

F1 · shares: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

F1 · price: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

SEC source: 0001415889-23-010456 · form4-06302023_080640.xml · nonDerivative · entry 1

Dall Marcia A · CIK 0001460624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,654

F1 · shares: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

F1 · price: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

SEC source: 0001415889-23-010455 · form4-06302023_080639.xml · nonDerivative · entry 1

Creager Robert E. · CIK 0001517566 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 50,254

F1 · shares: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

F1 · price: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

SEC source: 0001415889-23-010452 · form4-06302023_080616.xml · nonDerivative · entry 1

Terry Katharine · CIK 0001936853 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,654

F1 · shares: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

F1 · price: On June 29, 2023, the reporting person was granted a Restricted Stock Award in the amount of 3,988 shares of common stock. This award fully vests on June 29, 2024.

SEC source: 0001415889-23-009688 · form4-06132023_010639.xml · nonDerivative · entry 1

Hays James Charles · CIK 0001757909 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · JWayne, LLC

Disclosed balance after: 1,975,851

F1 · ownership.nature: The reporting person is the controlling member of the entity.

SEC source: 0001104659-23-083140 · tm2321828-1_4seq1.xml · nonDerivative · entry 2

WESTAIM CORP · CIK 0001108828 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,297,859

SEC source: 0001415889-23-010453 · form4-06302023_080622.xml · nonDerivative · entry 1

Creager Robert E. · CIK 0001517566 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 46,266

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: The reporting person was granted a Restricted Stock Award in the amount of ______ shares of common stock. This award fully vests on May 26, 2024.

F1 · price: The reporting person was granted a Restricted Stock Award in the amount of ______ shares of common stock. This award fully vests on May 26, 2024.

F2 · balance_after: On January 1, 2021, the reporting person was granted a Restricted Stock Award in the amount of 7,582 shares of common stock. This award fully vests on December 31, 2023. Also includes a Restricted Stock Award in the amount of 8,450 shares of common stock granted on January 1, 2021. This award fully vests on December 31, 2023.

SEC source: 0001415889-23-003651 · form4-03012023_090344.xml · derivative · entry 3

Duffy Sean W · CIK 0001936008 · EVP & CHIEF CLAIMS OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,861

Underlying: Common Stock · 2,861 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 2,861 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 2,861 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 2,861 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003651 · form4-03012023_090344.xml · derivative · entry 2

Duffy Sean W · CIK 0001936008 · EVP & CHIEF CLAIMS OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,861

Underlying: Common Stock · 2,861 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003654 · form4-03012023_090343.xml · derivative · entry 3

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,020

Underlying: Common Stock · 2,020 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003654 · form4-03012023_090343.xml · derivative · entry 2

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,020

Underlying: Common Stock · 2,020 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003657 · form4-03012023_090324.xml · derivative · entry 3

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,619

Underlying: Common Stock · 3,619 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 3,619 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 3,619 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 3,619 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003657 · form4-03012023_090324.xml · derivative · entry 2

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,619

Underlying: Common Stock · 3,619 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003653 · form4-03012023_090345.xml · derivative · entry 3

Robinson Andrew S · CIK 0001415833 · Director · CEO & PRESIDENT

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 15,151

Underlying: Common Stock · 15,151 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 15,151 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 15,151 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 15,151 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003653 · form4-03012023_090345.xml · derivative · entry 2

Robinson Andrew S · CIK 0001415833 · Director · CEO & PRESIDENT

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 15,151

Underlying: Common Stock · 15,151 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003658 · form4-03012023_090331.xml · derivative · entry 3

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,787

Underlying: Common Stock · 3,787 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 3,787 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 3,787 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 3,787 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003658 · form4-03012023_090331.xml · derivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,787

Underlying: Common Stock · 3,787 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003655 · form4-03012023_090335.xml · derivative · entry 3

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,020

Underlying: Common Stock · 2,020 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003655 · form4-03012023_090335.xml · derivative · entry 2

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,020

Underlying: Common Stock · 2,020 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003652 · form4-03012023_090354.xml · derivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CHIEF PEOPLE & ADMIN. OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,525

Underlying: Common Stock · 2,525 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 2,525 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 2,525 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 2,525 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003652 · form4-03012023_090354.xml · derivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CHIEF PEOPLE & ADMIN. OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,525

Underlying: Common Stock · 2,525 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003650 · form4-03012023_090333.xml · derivative · entry 3

Burkhart John A III · CIK 0001936023 · PRESIDENT - SPECIALTY LINES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,619

Underlying: Common Stock · 3,619 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 3,619 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 3,619 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 3,619 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003650 · form4-03012023_090333.xml · derivative · entry 2

Burkhart John A III · CIK 0001936023 · PRESIDENT - SPECIALTY LINES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,619

Underlying: Common Stock · 3,619 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

SEC source: 0001415889-23-003649 · form4-03012023_090343.xml · derivative · entry 3

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,020

Underlying: Common Stock · 2,020 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.exercise_date: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

F4 · derivative.expiration_date: On February 27, 2023, the reporting person was granted 2,020 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2026.

SEC source: 0001415889-23-003649 · form4-03012023_090343.xml · derivative · entry 2

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,020

Underlying: Common Stock · 2,020 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.

F3 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2026.