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  4. [Form 4] Skyward Specialty Insurance Group, Inc. Insider Trading Activity

Skyward Specialty (SKWD) CPO sells 8,397 shares in open-market trade

Filing Impact
(Moderate)
Filing Sentiment
(Negative)
Form Type
4

Rhea-AI Filing Summary

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.

Positive

  • None.

Negative

  • None.
Insider Schmitt Thomas N
Role CPO, Skyward Group
Sold 8,397 shs ($431K)
Type Security Shares Price Value
Sale Common Stock 8,397 $51.3235 $431K
Holdings After Transaction: Common Stock — 10,353 shares (Direct, null)
Footnotes (1)
  1. 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. 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.
Shares sold 8,397 shares Common Stock sold on June 12, 2026
Weighted average sale price $51.3235 per share Open-market sale on June 12, 2026
Post-transaction holdings 10,353 shares Shares directly held after June 12, 2026 sale
ESPP acquisition 191 shares Acquired June 5, 2026 under 2022 ESPP
Sale price range $51.30–$51.415 per share Multiple transactions included in reported sale
open-market sale financial
"transaction_action is described as an open-market sale of common stock"
An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.
weighted average prices financial
"Prices reported in Column 4 are weighted average prices"
Employee Stock Purchase Plan financial
"acquisition of 191 shares pursuant to the 2022 Employee Stock Purchase Plan"
An employee stock purchase plan is a company program that lets workers buy shares through small payroll deductions, often at a discount to the market price and after a set offering period. Think of it like a workplace savings plan that turns into ownership: it encourages employees to share in the company’s success and can create predictable buying or selling of stock that investors watch because it affects supply, demand and employee incentives.
ESPP purchase period financial
"for the ESPP purchase period of December 1, 2025 through May 31, 2026"
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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)
06/12/2026		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 Stock06/12/2026S8,397D$51.3235(1)10,353(2)D
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
Explanation of Responses:
1. 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.
2. 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.
/s/ Stacy E. Skelton, Attorney-in-Fact06/15/2026
** 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 transaction did Skyward Specialty (SKWD) report for Thomas N. Schmitt?

Thomas N. Schmitt reported an open-market sale of 8,397 Skyward Specialty common shares. The sale occurred on June 12, 2026, and was executed at a weighted average price of $51.3235 per share across multiple trades within a narrow price range.

At what price did Thomas N. Schmitt sell Skyward Specialty (SKWD) shares?

The reported weighted average sale price was $51.3235 per share. Individual trades took place between $51.30 and $51.415 per share, with the filing noting that full details of shares sold at each price are available upon request to the issuer or SEC staff.

How many Skyward Specialty (SKWD) shares does Thomas N. Schmitt hold after the sale?

After the reported open-market sale, Thomas N. Schmitt directly holds 10,353 shares of Skyward Specialty common stock. This holding figure comes from the Form 4 and reflects his position immediately following the June 12, 2026 transaction disclosed in the filing.

Was the Skyward Specialty (SKWD) insider sale a direct or indirect holding?

The Form 4 identifies the transaction as involving direct ownership. The direct_or_indirect field is coded as “D,” and the ownership_type is described as direct, indicating the shares are held directly by Thomas N. Schmitt rather than through another entity.

Did Thomas N. Schmitt recently acquire Skyward Specialty (SKWD) shares through an ESPP?

Yes. The filing notes an acquisition of 191 common shares on June 5, 2026, under the 2022 Employee Stock Purchase Plan. This purchase covered the ESPP period from December 1, 2025 through May 31, 2026 and is included in the reported holdings.

How many Skyward Specialty (SKWD) shares did Thomas N. Schmitt sell according to the Form 4?

The Form 4 shows that 8,397 shares of Skyward Specialty common stock were sold. This transaction is categorized as an open-market sale, using transaction code “S,” and is summarized as a net-sell of 8,397 shares in the transaction summary section.