Andrew S. Robinson - Jan 12, 2023 Form 4 Insider Report for Skyward Specialty Insurance Group, Inc. (SKWD)

Role: CEO & PRESIDENT, Director
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, 03:17 PM
Next filing: Mar 1, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
holding	SKWD	Common Stock						150K	Jan 12, 2023	Direct	F1

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	2023 RSU Grant (3-Year)	Award	$0	+100K		$0.00	100K	Jan 12, 2023	Common Stock	100K		Direct	F2, F3
transaction	SKWD	2023 RSU Grant (4-Year)	Award	$0	+100K		$0.00	100K	Jan 12, 2023	Common Stock	100K		Direct	F2, F4
transaction	SKWD	2023 Stock Options (Right-to-Buy)	Award	$0	+400K		$0.00	400K	Jan 12, 2023	Common Stock	400K	$15.00	Direct	F5

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

Explanation of Responses:

Id	Content
F1	The reporting person was granted 63,374 shares of Restricted Stock on March 17, 2021, as a match to shares purchased under the 2016 Employee Incentive Program. The first tranche vested on May 22, 2021. The second tranche vested on May 22, 2022. The third and final tranche of 21,124 shares immediately vested upon the closing of the Issuer's initial public offering on January 12, 2023. Also includes a Restricted Stock Award granted on January 1, 2022 in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025.
F2	Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock.
F3	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.
F4	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.
F5	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.