Skyward Specialty Insurance Group, Inc. Form 4 Filings

Skyward Specialty Insurance Group, Inc. Chief People Officer Thomas N. Schmitt reported an open-market sale of 8,397 shares of common stock on June 12, 2026 at a weighted average price of $51.3235 per share. After this transaction, he directly holds 10,353 shares.

The sale was executed through multiple trades within a price range of $51.30–$51.415. The reported holdings also reflect a prior acquisition of 191 shares under the company’s 2022 Employee Stock Purchase Plan for the purchase period from December 1, 2025 through May 31, 2026.

Skyward Specialty Insurance Group, Inc. director Anthony J. Kuczinski reported open-market purchases of a total of 2,000 shares of common stock on May 21, 2026, at prices of $47.00 and $47.20 per share, bringing his direct holdings to 15,977 shares.

Skyward Specialty Insurance Group director Gena L. Ashe reported RSU vesting and related share sales. On May 11, 2026, 1,797 Restricted Stock Units from a 2025 award converted into an equal number of common shares. To cover taxes and fees from this vesting, Ashe sold 740 common shares in open-market transactions at $46.35 per share. Following these transactions, Ashe directly holds 4,570 shares of common stock, reflecting a net increase in ownership from the RSU award.

Skyward Specialty Insurance Group, Inc. executive Thomas N. Schmitt reported compensation-related equity activity tied to performance share units. On May 6, 2026, he exercised derivative awards to acquire 3,358 shares of common stock and settled 2,525 performance share units (PSUs), each convertible into one share.

To cover tax withholding obligations from the PSU vesting and settlement, 1,322 shares were automatically withheld and disposed of, a transaction the company describes as mandated rather than discretionary. Following these transactions, Schmitt directly held 18,559 shares of common stock, and the PSU award granted in February 2023 is now fully vested and settled.

Skyward Specialty Insurance Group, Inc. reports that Head of Actuarial Sandip A. Kapadia settled a 2023 LTIP Performance Share Unit award on May 6, 2026. He exercised 2,020 PSUs granted on February 27, 2023, receiving 2,686 shares of Common Stock after the award fully vested based on performance through December 31, 2025.

In connection with this vesting, 1,374 shares were automatically withheld at $43.6800 per share to satisfy tax withholding obligations, a disposition mandated by the issuer and not discretionary. After these transactions, he directly owns 18,353 shares of Skyward Specialty common stock.

Skyward Specialty Insurance Group, Inc. Chief Information Officer Dan PK Bodnar reported the settlement of performance-based equity awards. On May 6, 2026, he acquired 2,686 shares of common stock upon settlement of Performance Share Units (PSUs) granted under the 2023 long-term incentive plan, following achievement of specified performance criteria through December 31, 2025.

In connection with this vesting and settlement, 1,004 shares were withheld to cover tax withholding obligations at a value of $43.68 per share. The filing states this tax-withholding disposition was mandated by the issuer and was not a discretionary transaction by Bodnar. After these transactions, he directly holds 28,147 shares of common stock.

Skyward Specialty Insurance Group, Inc. executive John A. Burkhart III, President US P&C, settled 3,619 Performance Share Units into Common Stock. In connection with this vesting, 1,894 shares were withheld at $43.68 per share to cover tax obligations. Following these compensation-related transactions, he directly holds 37,736 shares of Common Stock.

Skyward Specialty Insurance Group CFO Mark W. Haushill reported compensation-related share movements tied to performance awards. He exercised performance share units into 5,036 shares of Common Stock, with 1,982 shares withheld to satisfy tax obligations as mandated by the issuer. These tax-withholding dispositions were not open-market sales or discretionary trades. After the transactions, he directly holds 139,466 shares of Skyward Specialty Insurance Group, Inc. common stock.

Skyward Specialty Insurance Group Chairman & CEO Andrew S. Robinson settled a performance-based share award and had shares withheld for taxes. On May 6, 2026, he exercised 15,151 Performance Share Units (PSUs), each delivering one share of common stock upon settlement. In connection with this vesting, 7,930 shares of common stock were withheld at a price of $43.68 per share to satisfy tax withholding obligations, a disposition mandated by the company rather than a discretionary sale. Following these transactions, he holds 179,894 shares of common stock directly. The PSUs were originally granted on February 27, 2023 and vested based on performance criteria measured from January 1, 2023 through December 31, 2025, with settlement occurring after certification by the Compensation Committee.

Skyward Specialty Insurance Group EVP Sean W. Duffy reported equity compensation activity tied to performance share awards. On May 6, 2026, 2,861 Performance Share Units (PSUs) granted on February 27, 2023, fully vested based on performance from January 1, 2023 through December 31, 2025 and were settled in an equal number of common shares.

To cover related tax withholding obligations, 1,671 common shares were withheld, a disposition that the company mandated and that was not a discretionary market transaction. After these transactions, Duffy directly held 20,097 shares of Skyward Specialty Insurance Group common stock.

Terry Katharine reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. director Terry Katharine reported a new equity award. On May 6, 2026, she received a grant of 3,334 restricted stock units (RSUs), each representing one share of common stock after vesting and settlement.

The award will fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the award terms. Katharine has elected to defer settlement of this RSU award until her separation from the company under the Deferred Compensation Plan for Non-Employee Directors. Following the reported transactions, she directly holds 6,780 shares of common stock.

Peirce Christopher Locke reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. director Christopher Locke received a grant of 3,890 restricted stock units (RSUs). Each RSU represents the right to receive one share of the company’s common stock after vesting and settlement.

The award was granted on May 6, 2026 and is scheduled to fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the terms of the award agreement. Following the reported transactions, Locke holds 3,200 shares of common stock directly and 3,890 RSUs tied to common stock.

Skyward Specialty Insurance Group director receives RSU grant

Director Michael J. Morrissey reported a new award of 3,334 restricted stock units (RSUs) tied to Skyward Specialty Insurance Group, Inc. common stock. Each RSU will convert into one share after it vests and is settled.

The award was granted on May 6, 2026 and is scheduled to fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the award terms. Morrissey has elected to defer settlement of this RSU award until his separation from the company under the deferred compensation plan for non-employee directors. After the reported transactions, he holds 3,519 shares of common stock directly.

Skyward Specialty Insurance Group director Anthony J. Kuczinski reported equity compensation activity. On May 7, 2026, he exercised 1,797 restricted stock units from a 2025 award, receiving the same number of common shares and bringing his direct common stock holdings to 13,977 shares.

On May 6, 2026, he was granted a new 2026 RSU Award covering 3,334 RSUs. Each RSU settles into one share of common stock, and this award is scheduled to fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the award terms.

Dall Marcia A reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group director Marcia A. Dall received a new equity award. On May 6, 2026, she was granted 3,334 restricted stock units (RSUs), each representing the right to receive one share of the company’s Common Stock after vesting and settlement.

According to the award terms, the RSUs will fully vest on the date of Skyward Specialty’s 2027 Annual Meeting of Shareholders. Following the reported transactions, Dall holds 8,433 shares of Common Stock directly, and the new RSU award adds a deferred equity component tied to future service with the company.

Ashe Gena L reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group director Gena L. Ashe reported a new equity grant. On May 6, 2026, she received a 2026 RSU Award covering 3,334 restricted stock units (RSUs), each representing the right to receive one share of common stock after vesting and settlement.

The grant will fully vest on the date of Skyward Specialty’s 2027 Annual Meeting of Shareholders, subject to the award’s terms. Following the reported transactions, Ashe directly holds 3,513 shares of common stock, in addition to the new RSU award.

Skyward Specialty Insurance Group director James Charles Hays exercised a restricted stock unit award into 1,797 shares of Common Stock. The 2025 RSU award, granted on May 7, 2025, fully vested on May 5, 2026 and each RSU settled into one share at a stated price of $0.00 per share.

Following this non‑market exercise, Hays directly holds 175,858 shares of Skyward Specialty Insurance Group Common Stock. He also has indirect ownership through entities JWayne, LLC with 1,975,851 shares and Marquis Lafayette, LLC with 669,311 shares, reflecting significant continuing exposure to the company’s equity.

Skyward Specialty Insurance Group director Robert E. Creager increased his direct holdings of Common Stock through the settlement of a previously granted restricted stock unit (RSU) award. On May 5, 2026, 1,797 RSUs converted into 1,797 shares of Common Stock at no cash exercise price.

The RSUs were originally granted on May 7, 2025 and were subject to Board-approved accelerated vesting to align with the end of Creager’s director term at the company’s 2026 Annual Meeting of Shareholders. Following this RSU settlement, he directly holds 54,830 shares of Common Stock.

Skyward Specialty Insurance Group director Anthony J. Kuczinski bought additional common stock in open-market transactions. He purchased 2,000 shares at $46.8751 on February 27, 2,000 shares at $48.7911 on March 2, and 1,000 shares at $48.1321 on March 3, 2026, bringing his directly owned stake to 11,903 shares.

Skyward Specialty Insurance Group CFO Taryn Leonie McHarg reported buying a total of 200 shares of common stock of Skyward Specialty Insurance Group, Inc. in open-market transactions. The purchases occurred on February 27, 2026 at prices of $46.71 and $46.49 per share and are held indirectly as shares controlled by the reporting person as custodian. The filing also reports that McHarg directly owned 7,764 shares of common stock following these transactions.

Skyward Specialty Insurance Group director Peirce Christopher Locke bought 3,200 shares of common stock in an open-market purchase. The transaction took place on March 2, 2026 at a price of $47.30 per share. After this trade, he directly owns 3,200 shares.

Skyward Specialty Insurance Group Chairman and CEO Andrew S. Robinson reported open-market purchases of a total of 22,100 shares of common stock. The transactions were executed at weighted average prices of $46.57 and $46.94 per share across multiple trades within stated price ranges.

Following these purchases, Robinson directly owns 167,674 shares of Skyward Specialty Insurance Group common stock. Both transactions are classified as open-market purchases and increase his direct ownership stake.

McHarg Taryn Leonie reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. reported that executive Taryn Leonie McHarg received a grant of 37,854 Restricted Stock Units under the 2026 MIP. Each RSU represents one share of common stock upon settlement. According to the award terms, 50% of the RSUs vest on January 1, 2029 and the remaining 50% vest on January 1, 2030, contingent on continued service. The RSUs were granted at no cash cost per unit. Following this award, McHarg directly holds 7,764 shares of Skyward common stock.

Slaughter James Richard reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. reported that executive James Richard Slaughter, CUO - Apollo, received a grant of 108,154 Restricted Stock Units (RSUs) on February 25, 2026. Each RSU represents the right to receive one share of common stock upon settlement.

According to the award terms, 50% of these RSUs are scheduled to vest on January 1, 2029 and the remaining 50% on January 1, 2030, contingent on his continuous service. Following this filing, he reports direct ownership of 55,475 shares of common stock and indirect ownership of 12,724 shares through the Hillside Family Trust 2025, where he serves as trustee.

Ibeson David Christopher Ben reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. reported that Apollo division CEO David Christopher Ben Ibeson received a grant of 21,630 restricted stock units (RSUs) on February 25, 2026 under the 2026 MIP. Each RSU represents the right to receive one share of common stock upon settlement.

Subject to the award’s terms and his continued service, 50% of the RSUs are scheduled to vest on January 1, 2029 and the remaining 50% on January 1, 2030. Following this filing, he holds common stock directly and through The Ibeson Family Trust, where he serves as trustee.

Khan Shakoor reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. reported that Corporate Development Officer Shakoor Khan received multiple equity awards on February 25, 2026. He was granted 1,261 Restricted Stock Units (RSUs) under the 2026 LTIP that vest 100% on January 1, 2029, plus 4,326 RSUs under the 2026 Bright Future program, vesting 50% on January 1, 2029 and 50% on January 1, 2030, subject to continued service. He also received two separate Performance Stock Unit (PSU) awards of 1,261 units each, which can vest from 0% to 200% of the stated amount based on performance conditions and fully vest on December 31, 2028. Each RSU or PSU represents the right to receive one share of common stock upon settlement, and his directly held common stock position reflects prior purchases through the company’s Employee Stock Purchase Plan.

RYAN PATRICIA A. reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group granted equity awards to its Chief Legal Officer, Patricia A. Ryan. She received an award of 1,442 restricted stock units (RSUs) under the 2026 LTIP that will fully vest on January 1, 2029, assuming continued service.

Ryan was also granted two separate awards of 1,442 performance stock units (PSUs) each. Every PSU equals one share of common stock, and the number that ultimately vests can range from 0% to 200% of the granted amount, based on performance targets through December 31, 2028.

In addition, she received 10,815 RSUs under the 2026 Bright Future program. Half of these RSUs are scheduled to vest on January 1, 2029, and the remaining half on January 1, 2030, contingent on the terms of the RSU agreement and her continued service.

Skyward Specialty Insurance Group, Inc. Head of Actuarial Sandip A. Kapadia reported multiple equity compensation moves. He acquired common shares through the settlement of performance share units and received new grants of restricted stock units and additional performance share units under long-term incentive plans.

The new awards include 2,884 RSUs vesting on January 1, 2029, 2,884 PSUs that can vest between 0% and 200% of target and fully vest on December 31, 2028, and 4,326 RSUs vesting 50% on January 1, 2029 and 50% on January 1, 2030. Separately, 847 common shares were withheld at $45.89 per share to cover tax obligations, a disposition mandated by the company rather than a discretionary sale, leaving him with 17,041 common shares held directly.

Skyward Specialty Insurance Group Chief Information Officer Dan PK Bodnar reported multiple equity compensation transactions. On February 25, he acquired 2,343 shares of common stock through the exercise and settlement of 2,020 performance share units and received new equity awards, including 1,261 RSUs, 1,261 PSUs, and 4,326 additional RSUs under long-term incentive plans.

Footnotes explain that the 2023 PSUs vested based on performance criteria through December 31, 2025, and that the new 2026 RSU and PSU awards vest between December 31, 2028 and January 1, 2030, subject to continued service and performance conditions. On February 26, 876 shares of common stock were disposed of at $45.89 per share to cover tax withholding obligations required by the company, rather than a discretionary market sale. After these transactions, Bodnar directly owned 26,465 shares of common stock.

Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported multiple equity award events and related tax withholding. He acquired common stock through settlement of previously granted performance share units (PSUs), and received new 2026 long-term incentive awards in the form of restricted stock units (RSUs) and PSUs, each covering 1,442 units at a stated price of $0.00 per unit.

To cover tax obligations from the PSU vesting and settlement, 1,153 shares of common stock were withheld at $45.89 per share in a disposition mandated by the issuer and not a discretionary sale. After these transactions, Schmitt directly owned 16,523 shares of common stock.

Skyward Specialty Insurance Group EVP & CFO Mark W. Haushill reported multiple equity compensation moves. He acquired 3,787 common shares through settlement of previously granted performance share units (PSUs), then had 1,436 shares withheld at $45.89 per share to cover tax obligations, leaving him with 136,412 directly held common shares.

On February 25, 2026, he also received new long-term incentive awards: 4,326 restricted stock units (RSUs) that are scheduled to vest on January 1, 2029, plus two PSU grants of 4,326 units each that can vest between 0% and 200% based on performance through December 31, 2028. A prior 3,787-PSU award for the 2023–2025 period fully vested on December 31, 2025 and settled after Compensation Committee certification.

Skyward Specialty Insurance Group EVP & Chief Claims Officer Sean W. Duffy reported equity award activity and a related tax-withholding share disposition. On February 25, 2026, 2,861 performance share units granted in 2023 fully vested after meeting performance criteria and were settled into an equal number of common shares. On the same date, he received new equity awards: 1,442 RSUs vesting on January 1, 2029, 1,442 PSUs that can vest from 0% to 200% of target and fully vest on December 31, 2028, and 4,326 RSUs with 50% vesting on January 1, 2029 and 50% on January 1, 2030. A related Form 4 entry shows 1,391 common shares were disposed of at $45.89 per share on February 26, 2026 to satisfy tax withholding obligations mandated by the company, not as a discretionary trade, leaving him with 17,963 common shares held directly.

Skyward Specialty Insurance Group, Inc. Chairman and CEO Andrew S. Robinson reported several equity compensation events involving the company’s common stock and long-term incentive plan awards. These are primarily grants, vesting, and tax withholding transactions rather than open-market purchases or sales.

On February 25, 2026, 15,151 Performance Share Units (PSUs) granted in 2023 fully vested after achieving specified performance criteria and were settled in an equal number of common shares. On the same date, Robinson received a new award of 28,841 Restricted Stock Units (RSUs), which are scheduled to vest on January 1, 2029, subject to continuous service. He was also granted 28,841 new PSUs that can vest between 0% and 200% of this amount based on performance targets through December 31, 2028. Separately, on February 26, 2026, 6,916 shares of common stock were withheld at a price of $45.89 per share to satisfy tax obligations tied to the PSU vesting, a disposition mandated by the issuer and not a discretionary sale.

Skyward Specialty Insurance Group President, US P&C, John A. Burkhart III reported equity award activity and related tax withholding. He settled 3,619 Performance Share Units into Common Stock, with 1,652 shares withheld at $45.89 per share to cover tax obligations in a non‑discretionary transaction mandated by the company, leaving 34,817 Common shares held directly.

Burkhart also received new long-term incentives: a grant of 7,210 Restricted Stock Units that vest 100% on January 1, 2029, and two separate grants of 7,210 Performance Share Units each that fully vest on December 31, 2028. The PSUs can ultimately vest between 0% and 200% of the target amount based on specified performance criteria.

Skyward Specialty Insurance Group, Inc. chief people officer Thomas N. Schmitt reported a sale of 2,616 shares of common stock on February 9, 2026 at a weighted average price of $43.4916 per share. After this sale, he beneficially owned 14,747 shares directly.

The sale was executed under a pre-arranged Rule 10b5-1 trading plan that Schmitt adopted on September 11, 2025. The shares were sold in multiple trades at prices ranging from $43.15 to $43.78, with the weighted average price reported.

Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported stock activity tied to previously granted restricted stock units. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, both at an exercise price of $0. To satisfy tax withholding on these vestings, the issuer withheld 2,149 shares and 1,968 shares at a price of $46.10 per share, which the footnotes state was mandated by the company and not a discretionary sale by Schmitt. Following these transactions, Schmitt directly beneficially owned 17,363 shares of Skyward common stock, and 5,000 RSUs from the 4-year grant remain outstanding.

Skyward Specialty Insurance Group EVP & Chief Claims Officer Sean W. Duffy reported restricted stock unit vesting and related tax withholding transactions in company stock. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO RSU grant and another 5,000 shares were issued from a separate 2023 IPO RSU grant, both at an exercise price of $0. To cover tax obligations tied to these RSU vestings, the issuer withheld 2,276 shares and 2,095 shares at a price of $46.10 per share, which the filing notes as mandated by the company rather than discretionary sales by Duffy. Following these transactions, Duffy directly beneficially owned 16,036 shares of Skyward Specialty Insurance Group common stock.

Skyward Specialty Insurance Group Head of Actuarial Sandip A. Kapadia reported equity award activity tied to restricted stock units. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, with each RSU converting into one share of common stock at an exercise price of $0.

On the same date, the issuer withheld 1,985 shares and 1,808 shares of common stock, respectively, to satisfy tax withholding obligations, using a share value of $46.10 based on the closing price on the vesting date. After these transactions, Kapadia directly beneficially owned 15,545 shares of Skyward Specialty Insurance Group common stock. The filing states that the tax-related share withholding was mandated by the company and was not a discretionary sale.

Skyward Specialty Insurance Group, Inc. officer John A. Burkhart III, President, US P&C, reported equity transactions on January 12, 2026 related to restricted stock unit (RSU) awards. He settled a total of 13,330 RSUs into common stock, with 6,665 shares from a 4-year 2023 IPO RSU grant and 6,665 shares from a 3-year 2023 IPO RSU grant, each RSU converting into one share at an exercise price of $0. To cover tax withholding obligations on these vestings, the issuer withheld 2,798 shares and 2,623 shares of common stock at a price of $46.1 per share, as mandated under the company’s long-term incentive plan. After these transactions, Burkhart directly beneficially owned 32,271 shares of common stock.

Skyward Specialty Insurance Group Chairman and CEO Andrew S. Robinson reported the vesting and settlement of restricted stock units into common stock. On January 12, 2026, 100,000 RSUs from two 2023 IPO grants converted into 100,000 shares of common stock at an exercise price of $0. In connection with this vesting, a total of 39,532 shares were withheld by the company to cover tax obligations, using a share value of $46.10 on the vesting date. After these transactions, Robinson directly beneficially owned 134,915 shares of common stock. The 4-year IPO RSU grant shows 50,000 derivative RSUs remaining outstanding, while the 3-year IPO RSU grant is now fully settled.

Skyward Specialty Insurance Group’s reporting person, a director and Chairman & CEO, filed an amended insider trading report. The amendment explains that a prior Form 4 incorrectly showed the reported transactions as being made under a Rule 10b5-1 trading plan because that box was checked by mistake. The company states that all other details from that original filing remain correct. Following the reported transactions, the reporting person beneficially owns 74,447 shares of common stock directly.

Skyward Specialty Insurance Group Chief Information Officer Dan PK Bodnar reported vesting and settlement of restricted stock units and related tax withholding in company shares. On January 12, 2026, 5,000 common shares were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, each at an exercise price of $0. To satisfy tax obligations mandated by the company, 2,049 shares and 1,868 shares of common stock were withheld at a value of $46.10 per share based on the closing price on the vesting date. After these transactions, Bodnar directly held 24,998 shares of Skyward Specialty common stock. The RSU awards each originally covered 10,000 units, with vesting schedules tied to service through January 2025, 2026 and 2027.

Skyward Specialty Insurance Group EVP & CFO Mark W. Haushill reported the vesting and settlement of previously granted restricted stock units (RSUs) into common stock. On January 12, 2026, 6,665 shares were issued upon settlement of a 2023 IPO four-year RSU grant and another 6,665 shares were issued from a 2023 IPO three-year RSU grant, both at an exercise price of $0 per share. To cover tax withholding obligations tied to these vestings, the issuer withheld 2,797 shares and 2,623 shares at a price of $46.1 per share, transactions that were mandated by the company and not discretionary. Following these transactions, Haushill directly owned 133,456 shares of Skyward Specialty common stock.

Skyward Specialty Insurance Group, Inc. reported insider stock sales by its Head of Actuarial, an officer of the company, on 12/12/2025. The officer sold 1,486 shares of common stock at $50.03 per share and 1,200 shares at $50.01 per share, leaving 14,289 and then 13,089 shares beneficially owned directly after the respective transactions.

The sales were effected under a Rule 10b5-1 trading plan adopted on September 8, 2025. The reported share balance also reflects the acquisition of 231 shares on June 1, 2025 and 197 shares on December 1, 2025 through the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan "ESPP" for purchase periods from December 1, 2024 to May 31, 2025 and from June 1, 2025 to November 30, 2025.