SKWD

SEC source: 0001415889-24-006714 · form4-03052024_090321.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 137,696

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.95 to $36.5279, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, 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 range set forth above.

SEC source: 0001415889-24-006631 · form4-03052024_090353.xml · nonDerivative · entry 3

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,124

SEC source: 0001415889-24-006714 · form4-03052024_090321.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 154,942

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.90 to $36.56, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, 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 range set forth above.

SEC source: 0001415889-24-005855 · form4-02292024_090226.xml · derivative · entry 5

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 4,835 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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005855 · form4-02292024_090226.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,930

SEC source: 0001415889-24-005855 · form4-02292024_090226.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,811

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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005852 · form4-02292024_090239.xml · derivative · entry 5

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,844 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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005852 · form4-02292024_090239.xml · nonDerivative · entry 2

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,486

SEC source: 0001415889-24-005852 · form4-02292024_090239.xml · nonDerivative · entry 1

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,485

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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005858 · form4-02292024_090245.xml · derivative · entry 5

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 6,115 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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005858 · form4-02292024_090245.xml · nonDerivative · entry 2

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,446

SEC source: 0001415889-24-005858 · form4-02292024_090245.xml · nonDerivative · entry 1

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,730

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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005869 · form4-02292024_090214.xml · derivative · entry 4

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,133 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: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005869 · form4-02292024_090214.xml · nonDerivative · entry 1

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,635

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: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005865 · form4-02292024_090218.xml · derivative · entry 5

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,333 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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005865 · form4-02292024_090218.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,717

SEC source: 0001415889-24-005865 · form4-02292024_090218.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,709

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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005854 · form4-02292024_090223.xml · derivative · entry 5

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,689 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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005854 · form4-02292024_090223.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,792

SEC source: 0001415889-24-005854 · form4-02292024_090223.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,917

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: Upon vesting, each Performance Share Unit ("PSU") settles for one share of the Company's common stock.

SEC source: 0001415889-24-005856 · form4-02292024_090232.xml · nonDerivative · entry 1

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 171,688

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $36.0525 to $36.6145, inclusive. The reporting person undertakes to provide the issuer, any security holder of the issuer, 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 range set forth above.

SEC source: 0001415889-24-005530 · form4-02272024_090254.xml · nonDerivative · entry 3

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 191,688

F3 · price: Weighted average price. These shares were sold in multiple transactions at prices ranging from $35.35 to $36.35 inclusive. The reporting person undertakes to provide the issuer, any security holder of the issuer, 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 range set forth above.

SEC source: 0001415889-24-005855 · form4-02292024_090226.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,745

Underlying: Common Stock · 1,745 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 1,745 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 1,745 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 1,745 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, 2027.

SEC source: 0001415889-24-005855 · form4-02292024_090226.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,745

Underlying: Common Stock · 1,745 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005852 · form4-02292024_090239.xml · derivative · entry 4

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,495

Underlying: Common Stock · 1,495 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

SEC source: 0001415889-24-005852 · form4-02292024_090239.xml · derivative · entry 3

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,495

Underlying: Common Stock · 1,495 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005858 · form4-02292024_090245.xml · derivative · entry 4

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,144

Underlying: Common Stock · 2,144 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 2,144 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 2,144 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 2,144 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, 2027.

SEC source: 0001415889-24-005858 · form4-02292024_090245.xml · derivative · entry 3

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,144

Underlying: Common Stock · 2,144 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005863 · form4-02292024_090216.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,959

Underlying: Common Stock · 14,959 shares

Expires not disclosed

F3 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 14,959 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, 2027.

F3 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 14,959 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, 2027.

F3 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 14,959 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, 2027.

SEC source: 0001415889-24-005863 · form4-02292024_090216.xml · derivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,959

Underlying: Common Stock · 14,959 shares

Expires not disclosed

F1 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's common stock.

F2 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2027.

F2 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2027.

SEC source: 0001415889-24-005856 · form4-02292024_090232.xml · derivative · entry 3

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,490

Underlying: Common Stock · 3,490 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 3,490 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 3,490 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 3,490 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, 2027.

SEC source: 0001415889-24-005856 · form4-02292024_090232.xml · derivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,490

Underlying: Common Stock · 3,490 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005869 · form4-02292024_090214.xml · derivative · entry 3

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,495

Underlying: Common Stock · 1,495 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

SEC source: 0001415889-24-005869 · form4-02292024_090214.xml · derivative · entry 2

Shaunty Leslie · CIK 0001937463 · GENERAL COUNSEL & SECRETARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,495

Underlying: Common Stock · 1,495 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005865 · form4-02292024_090218.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,495

Underlying: Common Stock · 1,495 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 1,495 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, 2027.

SEC source: 0001415889-24-005865 · form4-02292024_090218.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,495

Underlying: Common Stock · 1,495 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005859 · form4-02292024_090246.xml · derivative · entry 3

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,745

Underlying: Common Stock · 1,745 shares

Expires not disclosed

F3 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 1,745 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, 2027.

F3 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 1,745 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, 2027.

F3 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 1,745 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, 2027.

SEC source: 0001415889-24-005859 · form4-02292024_090246.xml · derivative · entry 2

Kapadia Sandip A · CIK 0001937132 · EVP, CHIEF ACTUARY

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,745

Underlying: Common Stock · 1,745 shares

Expires not disclosed

F1 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's common stock.

F2 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2027.

F2 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2027.

SEC source: 0001415889-24-005854 · form4-02292024_090223.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,490

Underlying: Common Stock · 3,490 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 27, 2024, the reporting person was granted 3,490 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, 2027.

F4 · derivative.exercise_date: On February 27, 2024, the reporting person was granted 3,490 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, 2027.

F4 · derivative.expiration_date: On February 27, 2024, the reporting person was granted 3,490 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, 2027.

SEC source: 0001415889-24-005854 · form4-02292024_090223.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,490

Underlying: Common Stock · 3,490 shares

Expires not disclosed

F2 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's 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, 2027.

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, 2027.

SEC source: 0001415889-24-005530 · form4-02272024_090254.xml · nonDerivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 236,688

F2 · price: Weighted average price. These shares were sold in multiple transactions at prices ranging from $35.2908 to $35.9250 inclusive. The reporting person undertakes to provide the issuer, any security holder of the issuer, 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 range set forth above.

SEC source: 0001415889-24-005530 · form4-02272024_090254.xml · nonDerivative · entry 1

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 261,688

F1 · price: Weighted average price. These shares were sold in multiple transactions at prices ranging from $35.40 to $36.70 inclusive. The reporting person undertakes to provide the issuer, any security holder of the issuer, 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 range set forth above.

SEC source: 0001415889-24-000310 · form4-01032024_090125.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 4,788 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 4,788 RSUs. This award fully vested on January 1, 2024.

F2 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 4,788 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000310 · form4-01032024_090125.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,976

SEC source: 0001415889-24-000310 · form4-01032024_090125.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,093

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: 0001415889-24-000307 · form4-01032024_090124.xml · derivative · entry 3

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,816 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 2,816 RSUs. This award fully vested on January 1, 2024.

F3 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 2,816 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000307 · form4-01032024_090124.xml · nonDerivative · entry 2

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,641

SEC source: 0001415889-24-000307 · form4-01032024_090124.xml · nonDerivative · entry 1

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,758

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 324 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: 0001415889-24-000313 · form4-01032024_090120.xml · derivative · entry 3

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 6,055 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 6,055 RSUs. This award fully vested on January 1, 2024.

F2 · derivative.expiration_date: On January 1, 2021, the reporting person was granted 6,055 RSUs. This award fully vested on January 1, 2024.

SEC source: 0001415889-24-000313 · form4-01032024_090120.xml · nonDerivative · entry 2

Hill Kirby · CIK 0001935898 · PRESIDENT - INDUSTRY SOLUTIONS

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,615