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Schmitt Thomas N

Disclosed activity across 1 company

Tapewire entity
38062
SEC CIK
0001937316

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
Skyward Specialty Insurance Group, Inc.SKWD · Entity 4400CPO, Skyward GroupJune 12, 2026June 15, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

Skyward Specialty Insurance Group, Inc.

Report date June 12, 2026 · Filed June 15, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect10,353 Reported balance After 2026-06-12 transaction · row 1 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 1 · 2026-06-12 · Sale · Disposed 8,397 · Balance 10,353

F1: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $51.30-$51.415, inclusive (weighted average of $51.3235). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

F2: The number of securities reported reflects the June 5, 2026 acquisition of 191 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 December 1, 2025 through May 31, 2026.

Filing footnotes · ownership attribution and instrument terms

F1: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $51.30-$51.415, inclusive (weighted average of $51.3235). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

F2: The number of securities reported reflects the June 5, 2026 acquisition of 191 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 December 1, 2025 through May 31, 2026.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
June 12, 2026 Filed Jun 15, 2026 21:13 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 8,397 $51.32 $430,963.43
Disclosure

SEC source: 0001937316-26-000012 · form4-06152026_090627.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,353

F1 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $51.30-$51.415, inclusive (weighted average of $51.3235). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

F2 · balance_after: The number of securities reported reflects the June 5, 2026 acquisition of 191 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 December 1, 2025 through May 31, 2026.

Read SEC document
May 06, 2026 Filed May 8, 2026 20:56 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 LTIP - PSUs · Derivative 2,525 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000010 · form4-05082026_080503.xml · derivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,525 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.

F3 · derivative.exercise_price: Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F4 · derivative.exercise_date: On February 27, 2023, the Reporting Person was awarded 2,525 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

F4 · derivative.expiration_date: On February 27, 2023, the Reporting Person was awarded 2,525 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

Read SEC document
May 06, 2026 Filed May 8, 2026 20:56 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 1,322 $43.68 $57,744.96
Disclosure

SEC source: 0001937316-26-000010 · form4-05082026_080503.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,559

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

Read SEC document
May 06, 2026 Filed May 8, 2026 20:56 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 3,358 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000010 · form4-05082026_080503.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,881

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: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II.

Read SEC document
February 26, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 1,153 $45.89 $52,911.17
Disclosure

SEC source: 0001937316-26-000008 · form4-02272026_040208.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,523

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2026 LTIP - PSUs · Derivative 1,442 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000008 · form4-02272026_040208.xml · derivative · entry 6

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,442

Underlying: Common Stock · 1,442 shares

Expires not disclosed

F8 · derivative.exercise_price: On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

F8 · derivative.exercise_date: On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

F8 · derivative.expiration_date: On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2026 LTIP - PSUs · Derivative 1,442 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000008 · form4-02272026_040208.xml · derivative · entry 5

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,442

Underlying: Common Stock · 1,442 shares

Expires not disclosed

F7 · derivative.exercise_price: On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

F7 · derivative.exercise_date: On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

F7 · derivative.expiration_date: On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2026 LTIP - RSUs · Derivative 1,442 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000008 · form4-02272026_040208.xml · derivative · entry 4

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,442

Underlying: Common Stock · 1,442 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 1,442 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.

F6 · derivative.expiration_date: On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 1,442 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 LTIP - PSUs · Derivative 2,525 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000008 · form4-02272026_040208.xml · derivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,525 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.

F3 · derivative.exercise_price: Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F4 · derivative.exercise_date: On February 27, 2023, the Reporting Person was awarded 2,525 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

F4 · derivative.expiration_date: On February 27, 2023, the Reporting Person was awarded 2,525 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 2,929 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000008 · form4-02272026_040208.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,676

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: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II.

Read SEC document
February 09, 2026 Filed Feb 10, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 2,616 $43.49 $113,774.03
Disclosure

SEC source: 0001937316-26-000006 · form4-02102026_040201.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 14,747

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 11, 2025.

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $43.15-$43.78, inclusive (weighted average of $43.49167813). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:09 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 IPO RSU Grant (3-Year) · Derivative 5,000 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · derivative · entry 6

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:09 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 IPO RSU Grant (4-Year) · Derivative 5,000 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · derivative · entry 5

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,000

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:09 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 1,968 $46.10 $90,724.80
Disclosure

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 4

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,363

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:09 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 5,000 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,331

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: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:09 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 2,149 $46.10 $99,068.90
Disclosure

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,331

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:09 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 5,000 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,480

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: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

Read SEC document
January 01, 2026 Filed Jan 5, 2026 21:40 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 LTIP - RSUs · Derivative 2,525 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000002 · form4-01052026_090134.xml · derivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,525 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,525 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

F5 · derivative.expiration_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,525 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

Read SEC document
January 01, 2026 Filed Jan 5, 2026 21:40 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 1,004 $51.11 $51,314.44
Disclosure

SEC source: 0001937316-26-000002 · form4-01052026_090134.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,480

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock for the trading day immediately preceding the vesting date, December 31, 2025, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

Read SEC document
January 01, 2026 Filed Jan 5, 2026 21:40 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 2,525 $0.00 $0.00
Disclosure

SEC source: 0001937316-26-000002 · form4-01052026_090134.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,484

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: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

Read SEC document
December 11, 2025 Filed Dec 11, 2025 22:29 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 88 $47.61 $4,189.68
Disclosure

SEC source: 0001937316-25-000003 · form4-12112025_101241.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,959

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 11, 2025.

F2 · balance_after: The number of securities reported reflects the June 1, 2025 acquisition of 152 shares and the December 1, 2025 acquisition of 168 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 periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

Read SEC document
March 06, 2025 Filed Mar 10, 2025 20:37 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 IPO RSU Grant (3-Year) · Derivative 5,000 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-007535 · form4-03102025_080300.xml · derivative · entry 6

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,000

Underlying: Common Stock · 5,000 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.

F6 · security: On January 12, 2023, in conjunction with the Company's IPO the Reporting Person was granted an RSU award in the amount of 10,000 RSUs; 5,000 of the RSUs vested on January 12, 2025 and settled on March 6, 2025. The remaining 5,000 RSUs will fully vest on January 12, 2026 subject to the Reporting Person's continuous service through the vesting date.

F4 · derivative.exercise_price: Each Restricted Stock Unit ("RSU") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F6 · derivative.exercise_date: On January 12, 2023, in conjunction with the Company's IPO the Reporting Person was granted an RSU award in the amount of 10,000 RSUs; 5,000 of the RSUs vested on January 12, 2025 and settled on March 6, 2025. The remaining 5,000 RSUs will fully vest on January 12, 2026 subject to the Reporting Person's continuous service through the vesting date.

F6 · derivative.expiration_date: On January 12, 2023, in conjunction with the Company's IPO the Reporting Person was granted an RSU award in the amount of 10,000 RSUs; 5,000 of the RSUs vested on January 12, 2025 and settled on March 6, 2025. The remaining 5,000 RSUs will fully vest on January 12, 2026 subject to the Reporting Person's continuous service through the vesting date.

Read SEC document
March 06, 2025 Filed Mar 10, 2025 20:37 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2022 LTIP - PSUs · Derivative 4,604 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-007535 · form4-03102025_080300.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 · 4,604 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 Performance Stock Unit ("PSU") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F5 · derivative.exercise_date: On January 1, 2022, the Reporting Person was awarded 3,799 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. Each PSU is equivalent to one share of the Company's Common Stock. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on January 1, 2025 and settled upon certification by the Compensation Committee.

F5 · derivative.expiration_date: On January 1, 2022, the Reporting Person was awarded 3,799 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. Each PSU is equivalent to one share of the Company's Common Stock. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on January 1, 2025 and settled upon certification by the Compensation Committee.

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March 06, 2025 Filed Mar 10, 2025 20:37 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 1,928 $50.24 $96,862.53
Disclosure

SEC source: 0001415889-25-007535 · form4-03102025_080300.xml · nonDerivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,727

F2 · kind: Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs and PSUs reported on this Form 4.

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $49.53- $51.47, inclusive (weighted average of $50.2399). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

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March 06, 2025 Filed Mar 10, 2025 20:37 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 5,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001415889-25-007535 · form4-03102025_080300.xml · nonDerivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,655

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.

F4 · price: Each Restricted Stock Unit ("RSU") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

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March 06, 2025 Filed Mar 10, 2025 20:37 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 1,697 $50.24 $85,257.11
Disclosure

SEC source: 0001415889-25-007535 · form4-03102025_080300.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,655

F2 · kind: Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs and PSUs reported on this Form 4.

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $49.53- $51.47, inclusive (weighted average of $50.2399). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

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March 06, 2025 Filed Mar 10, 2025 20:37 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 4,406 Not disclosed Not disclosed
Disclosure

SEC source: 0001415889-25-007535 · form4-03102025_080300.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,352

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 Performance Stock Unit ("PSU") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

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March 03, 2025 Filed Mar 4, 2025 22:12 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 6,300 $51.92 $327,096.00
Disclosure

SEC source: 0001415889-25-006599 · form4-03042025_100340.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 3,946

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 September 3, 2024.

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February 25, 2025 Filed Feb 27, 2025 22:38 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2025 LTIP - PSUs · Derivative 1,182 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-005881 · form4-02272025_100253.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,182

Underlying: Common Stock · 1,182 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 25, 2025, the Reporting Person was granted 1,182 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 December 31, 2027.

F4 · derivative.exercise_date: On February 25, 2025, the Reporting Person was granted 1,182 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 December 31, 2027.

F4 · derivative.expiration_date: On February 25, 2025, the Reporting Person was granted 1,182 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 December 31, 2027.

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February 25, 2025 Filed Feb 27, 2025 22:38 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2025 LTIP - PSUs · Derivative 1,182 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-005881 · form4-02272025_100253.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,182

Underlying: Common Stock · 1,182 shares

Expires not disclosed

F3 · derivative.exercise_price: On February 25, 2025, the Reporting Person was granted 1,182 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 December 31, 2027.

F3 · derivative.exercise_date: On February 25, 2025, the Reporting Person was granted 1,182 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 December 31, 2027.

F3 · derivative.expiration_date: On February 25, 2025, the Reporting Person was granted 1,182 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 December 31, 2027.

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February 25, 2025 Filed Feb 27, 2025 22:38 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2025 LTIP - RSUs · Derivative 1,182 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-005881 · form4-02272025_100253.xml · derivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,182

Underlying: Common Stock · 1,182 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, 2028.

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, 2028.

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January 06, 2025 Filed Jan 7, 2025 00:25 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 546 $46.85 $25,581.74
Disclosure

SEC source: 0001415889-25-000908 · form4-01072025_120141.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 10,246

F1 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 3,799 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F2 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $46.61 to $49.01, 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.

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January 03, 2025 Filed Jan 7, 2025 00:25 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 637 $47.81 $30,453.70
Disclosure

SEC source: 0001415889-25-000908 · form4-01072025_120141.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 10,792

F1 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 3,799 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F2 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $46.61 to $49.01, 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.

F4 · balance_after: The number of securities reported reflects the May 31, 2024 acquisition of 381 shares and the December 1, 2024 acquisition of 331 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 periods of December 1, 2023 through May 31, 2024, and June 1, 2024 through November 30, 2024, respectively.

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February 29, 2024 Filed Feb 29, 2024 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2021 LTIP - Performance Share Units · Derivative 5,333 $0.00 $0.00
Disclosure

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.

Read SEC document
February 29, 2024 Filed Feb 29, 2024 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 1,992 $36.47 $72,648.24
Disclosure

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

Read SEC document
February 29, 2024 Filed Feb 29, 2024 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 5,333 Not disclosed Not disclosed
Disclosure

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.

Read SEC document
February 27, 2024 Filed Feb 29, 2024 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2024 LTIP - Performance Share Units · Derivative 1,495 $0.00 $0.00
Disclosure

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.

Read SEC document
February 27, 2024 Filed Feb 29, 2024 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2024 LTIP - Common Stock · Derivative 1,495 $0.00 $0.00
Disclosure

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.

Read SEC document
January 01, 2024 Filed Jan 3, 2024 21:46 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionRestricted Stock Unit · Derivative 5,281 Not disclosed Not disclosed
Disclosure

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.

Read SEC document
January 01, 2024 Filed Jan 3, 2024 21:46 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 2,234 $33.88 $75,687.92
Disclosure

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

Read SEC document
January 01, 2024 Filed Jan 3, 2024 21:46 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 5,281 Not disclosed Not disclosed
Disclosure

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.

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February 27, 2023 Filed Mar 1, 2023 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2023 LTIP - Performance Units · Derivative 2,525 $0.00 $0.00
Disclosure

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.

Read SEC document
February 27, 2023 Filed Mar 1, 2023 21:17 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2023 LTIP - Common Stock · Derivative 2,525 $0.00 $0.00
Disclosure

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.

Read SEC document
January 12, 2023 Filed Jan 17, 2023 21:21 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2023 Stock Options (Right-to-Buy) · Derivative 40,000 $0.00 Strike: $15.00 $0.00
Disclosure

SEC source: 0001415889-23-001032 · form4-01172023_090134.xml · derivative · entry 4

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 40,000

Underlying: Common Stock · 40,000 shares

Expires not disclosed

F5 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 50% of the options will vest on January 12, 2026, and the remaining 50% will vest on January 12, 2027.

F5 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 50% of the options will vest on January 12, 2026, and the remaining 50% will vest on January 12, 2027.

Read SEC document
January 12, 2023 Filed Jan 17, 2023 21:21 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2023 RSU Grant (4-Year) · Derivative 10,000 $0.00 $0.00
Disclosure

SEC source: 0001415889-23-001032 · form4-01172023_090134.xml · derivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,000

Underlying: Common Stock · 10,000 shares

Expires not disclosed

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

F4 · derivative.exercise_date: Subject to the reporting person's continuous service through the vesting date, 50% of the RSUs will vest on January 12, 2026, and the remaining 50% will vest on January 12, 2027.

F4 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 50% of the RSUs will vest on January 12, 2026, and the remaining 50% will vest on January 12, 2027.

Read SEC document
January 12, 2023 Filed Jan 17, 2023 21:21 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2023 RSU Grant (3-Year) · Derivative 10,000 $0.00 $0.00
Disclosure

SEC source: 0001415889-23-001032 · form4-01172023_090134.xml · derivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,000

Underlying: Common Stock · 10,000 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, 50% of the RSUs shall vest on January 12, 2025, and the remaining 50% will vest on January 12, 2026.

F3 · derivative.expiration_date: Subject to the reporting person's continuous service through the vesting date, 50% of the RSUs shall vest on January 12, 2025, and the remaining 50% will vest on January 12, 2026.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.