Kirby Hill - Jan 12, 2023 Form 4 Insider Report for Skyward Specialty Insurance Group, Inc. (SKWD)

Role: PRESIDENT - INDUSTRY SOLUTIONS
Signature: /s/ Stacy E. Skelton, Attorney-in-Fact
Stock symbol: SKWD
Transactions as of: Jan 12, 2023
Transactions value $: $0
Form type: 4
Date filed: 1/17/2023, 03:20 PM
Next filing: Mar 1, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	SKWD	Common Stock	Conversion of derivative security		+4.82K	+46.95%		15.1K	Jan 12, 2023	Direct	F1, F2

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	SKWD	Preferred Series A Stock	Conversion of derivative security		-582	-100%		0	Jan 12, 2023	Preferred Series A Stock	582		Direct	F1
transaction	SKWD	2023 RSU Grant (3-Year)	Award	$0	+13.3K		$0.00	13.3K	Jan 12, 2023	Common Stock	13.3K		Direct	F3, F4
transaction	SKWD	2023 RSU Grant (4-Year)	Award	$0	+13.3K		$0.00	13.3K	Jan 12, 2023	Common Stock	13.3K		Direct	F3, F5
transaction	SKWD	2023 Stock Options (Right-to-Buy)	Award	$0	+53.3K		$0.00	53.3K	Jan 12, 2023	Common Stock	53.3K	$15.00	Direct	F6

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	The reporting person owned 581.935 shares of the Company's Series-A Convertible Preferred stock, which was converted into 4,817 shares of Common Stock upon the consummation of the Company's IPO.
F2	Includes a Restricted Stock Award in the amount of 5,445 shares granted on January 1, 2022. Each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025.
F3	Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.
F4	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.
F5	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.
F6	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.