Apollo CEO at Skyward Specialty (SKWD) awarded 21,630 RSUs

Rhea-AI Filing Summary

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.

Insider Trade Summary

3 transactions reported

Mixed 3 txns

Insider Ibeson David Christopher Ben

Role CEO - Apollo

Type	Security	Shares	Price	Value
Grant/Award	2026 MIP - RSUs	21,630	$0.00	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: 2026 MIP - RSUs — 21,630 shares (Direct); Common Stock — 266,867 shares (Direct); Common Stock — 79,708 shares (Indirect, The Ibeson Family Trust)

Footnotes (1)

1. The Reporting Person is Trustee of the entity. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 21,630 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED 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^*

Ibeson David Christopher Ben

(Last) (First) (Middle)

800 GESSNER ROAD

SUITE 600

(Street)

HOUSTON TX 77024

(City) (State) (Zip)

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)

	Director		10% Owner
X	Officer (give title below)	X	Other (specify below)
	CEO - Apollo		Division of Skyward Group

3. Date of Earliest Transaction (Month/Day/Year)
02/25/2026

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock								266,867	D
Common Stock								79,708	I	The Ibeson Family Trust(1)

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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
2026 MIP - RSUs	(2)	02/25/2026		A		21,630		(3)	(3)	Common Stock	21,630	$0	21,630	D

Explanation of Responses:

1. The Reporting Person is Trustee of the entity.

2. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.

3. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 21,630 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

	/s/ Stacy E. Skelton, Attorney-in-Fact	02/27/2026
	** Signature of Reporting Person	Date
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.

FAQ

What insider transaction did Skyward Specialty Insurance Group (SKWD) report for David Ibeson?

Skyward Specialty reported that Apollo division CEO David Ibeson received a grant of 21,630 restricted stock units. The award was granted on February 25, 2026 under the 2026 MIP and represents a non-cash equity incentive tied to future vesting dates.

How many RSUs did Skyward Specialty’s Apollo CEO receive in this Form 4?

David Ibeson was granted 21,630 restricted stock units. These RSUs were awarded on February 25, 2026 and are structured to vest in two equal installments, providing a long-term equity incentive aligned with continued service at Skyward Specialty Insurance Group.

What is the vesting schedule for David Ibeson’s 21,630 RSUs at Skyward Specialty (SKWD)?

Half of David Ibeson’s 21,630 RSUs are scheduled to vest on January 1, 2029, with the remaining half vesting on January 1, 2030. Vesting is subject to the RSU agreement terms and his continuous service through those dates.

What does each RSU granted to David Ibeson by Skyward Specialty represent?

Each restricted stock unit granted to David Ibeson represents the right to receive one share of Skyward Specialty’s common stock upon settlement. This structure ties his potential future ownership directly to the company’s equity, rather than providing immediate cash compensation.

How are David Ibeson’s indirect Skyward Specialty (SKWD) holdings structured?

In addition to directly held common stock, David Ibeson has indirect ownership through The Ibeson Family Trust. He serves as trustee of this entity, which holds common stock on his behalf, as reflected in the Form 4’s indirect ownership disclosure and related footnote.