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Skyward Specialty (SKWD) CPO settles PSU award with tax-share withholding

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

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 19,881 shares of common stock, and the PSU award granted in February 2023 is now fully vested and settled.

Positive

  • None.

Negative

  • None.
Insider Schmitt Thomas N
Role CPO, Skyward Group
Type Security Shares Price Value
Exercise 2023 LTIP - PSUs 2,525 $0.00 --
Exercise Common Stock 3,358 $0.00 --
Tax Withholding Common Stock 1,322 $43.68 $58K
Holdings After Transaction: 2023 LTIP - PSUs — 0 shares (Direct, null); Common Stock — 19,881 shares (Direct, null)
Footnotes (1)
  1. 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. 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. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement. 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.
Shares withheld for taxes 1,322 shares Tax withholding disposition on May 6, 2026
Shares acquired via exercise 3,358 shares Common stock from derivative exercise on May 6, 2026
PSUs settled 2,525 units 2023 LTIP PSUs settled into common stock
Post-transaction holdings 19,881 shares Common stock held directly after transactions
PSU performance period Jan 1, 2023–Dec 31, 2025 Period over which PSU performance criteria applied
PSU vesting range 0%–150% Possible vesting outcomes relative to target PSUs
Performance Share Units financial
"settlement of the Performance Share Units ("PSUs") listed in Line I"
Performance share units are a type of company stock award given to employees that depend on the company meeting specific goals or targets. If these goals are achieved, the employee receives shares or the value of shares; if not, they may receive little or no compensation. This aligns employees’ interests with the company's success and encourages performance that benefits investors.
tax withholding obligations financial
"shares withheld to cover tax withholding obligations in connection with the vesting"
vesting and settlement financial
"in connection with the vesting and settlement of the PSUs listed in Line I"
Compensation Committee financial
"settled upon certification by the Compensation Committee of the Board of Directors"
A compensation committee is a group within a company's leadership responsible for setting and reviewing how much top executives and employees are paid, including salaries, bonuses, and benefits. It matters to investors because fair and effective pay decisions can influence a company's performance, leadership motivation, and overall governance, helping ensure that the company’s management is aligned with shareholders’ interests.
PSUs financial
"The number of PSUs subject to vest under this award can range"
PSUs are company shares promised to employees or executives that only become actual stock if the business hits specific performance targets over a set period. For investors, PSUs matter because they link pay to measurable outcomes — similar to a conditional bonus that converts into ownership — which can influence management decisions, dilution of shares, and signals about confidence in future results.
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Schmitt Thomas N
(Last)(First)(Middle)
800 GESSNER
SUITE 600
(Street)
HOUSTON TEXAS 77024
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Skyward Specialty Insurance Group, Inc. [ SKWD ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
CPO, Skyward Group
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/06/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock05/06/2026M3,358(1)A$019,881D
Common Stock05/06/2026F(2)1,322D$43.6818,559D
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
2023 LTIP - PSUs(3)05/06/2026M2,525 (4) (4)Common Stock2,525$00D
Explanation of Responses:
1. 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.
2. 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.
3. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.
4. 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.
/s/ Stacy E. Skelton, Attorney-in-Fact05/08/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did SKWD executive Thomas N. Schmitt report?

Thomas N. Schmitt reported equity transactions tied to performance share units. He exercised derivative awards to acquire common stock and had shares automatically withheld to satisfy tax obligations when the PSUs vested and settled, all as part of his compensation program.

How many Skyward Specialty (SKWD) shares were withheld for taxes?

A total of 1,322 Skyward Specialty common shares were withheld. These shares covered tax withholding obligations arising from the vesting and settlement of performance share units and were characterized as a mandated, non-discretionary disposition by the issuer, rather than an open-market sale.

How many Skyward Specialty (SKWD) shares did Schmitt acquire through exercises?

Schmitt acquired 3,358 shares of Skyward Specialty common stock through the exercise or conversion of derivative awards. These shares were obtained in connection with the settlement of performance share units, reflecting compensation earned rather than an open-market stock purchase transaction.

What are the terms of the 2,525 Skyward Specialty (SKWD) PSUs?

The 2,525 performance share units each entitled Schmitt to one share of Skyward Specialty common stock upon settlement. Granted on February 27, 2023, they were tied to performance from January 1, 2023 through December 31, 2025, with vesting ranging from 0% to 150% of the target amount.

When did the Skyward Specialty (SKWD) PSU award fully vest and settle?

The PSU award fully vested on December 31, 2025 and settled after the Compensation Committee certified performance. At settlement, the PSUs converted into common stock, and a portion of the resulting shares was withheld to cover tax obligations associated with the vesting event.

How many Skyward Specialty (SKWD) shares does Schmitt hold after these transactions?

After the reported transactions, Schmitt directly holds 19,881 shares of Skyward Specialty common stock. This figure reflects his position after exercising derivative awards and the automatic withholding of some shares to satisfy tax obligations tied to the PSU vesting and settlement.