Guidewire CAO reports tax-related sale of 999 shares

Guidewire Software, Inc. Chief Administrative Officer and General Counsel James Winston King reported a small share sale tied to tax obligations.

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Administrative Officer and General Counsel James Winston King reported a small share sale tied to tax obligations. He disposed of 999 shares of common stock at $118.743 per share, with the shares sold by the company to cover taxes from the settlement of Restricted Stock Units. Following the transaction, he directly holds 31,702 common shares, indicating the sale represents only a minor portion of his overall stake.

Insider Trade Summary

Net Seller: 999 shares

Net Sell 1 txn

Insider King James Winston

Role Chief Admin Officer, Gen Couns

Sold 999 shs ($119K)

Type	Security	Shares	Price	Value
Sale	Common Stock	999	$118.743	$119K

Holdings After Transaction: Common Stock — 31,702 shares (Direct)

Footnotes (1)

1. F1. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

Key Figures

Shares sold: 999 shares Sale price per share: $118.743 per share Shares owned after transaction: 31,702 shares

3 metrics

Shares sold 999 shares Common stock disposed in tax-related sale on June 16, 2026

Sale price per share $118.743 per share Price for common stock sold in reported transaction

Shares owned after transaction 31,702 shares Direct common stock holdings following the Form 4 transaction

Key Terms

Restricted Stock Units, open-market sale, Form 4, Common Stock

4 terms

Restricted Stock Units financial

"Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units."

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

open-market sale financial

"transaction_action: open-market sale"

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.

Form 4 regulatory

"INSIDER FILING DATA (Form 4)"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

Common Stock financial

"security_title: Common Stock"

Common stock represents ownership shares in a company, giving investors a stake in its success and a say in important decisions through voting rights. It is the most common type of stock traded on markets and can provide income through dividends, as well as potential for value growth. For investors, holding common stock means sharing in the company’s profits and risks.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Guidewire (GWRE) report for James Winston King?

Guidewire disclosed that James Winston King reported selling 999 shares of common stock. The shares were sold at $118.743 each, with the transaction made to cover taxes related to the settlement of Restricted Stock Units rather than a discretionary open-market sale.

What role does James Winston King hold at Guidewire (GWRE)?

James Winston King serves as Guidewire’s Chief Administrative Officer and General Counsel. This means he holds a senior executive position overseeing legal and administrative matters, so his equity transactions are closely tracked as part of standard insider reporting requirements.

How many Guidewire (GWRE) shares did James Winston King sell and at what price?

He sold 999 shares of Guidewire common stock at a price of $118.743 per share. The filing notes that these shares were sold by the issuer specifically to cover taxes arising from the settlement of Restricted Stock Units granted to him.

How many Guidewire (GWRE) shares does James Winston King own after this transaction?

After the reported transaction, James Winston King directly owns 31,702 shares of Guidewire common stock. This indicates that the 999 shares sold for tax purposes represent a relatively small fraction of his total reported direct holdings in the company.

Was the Guidewire (GWRE) insider sale a tax-related transaction?

Yes. A footnote explains that the 999 shares were sold by the issuer to cover taxes associated with the settlement of Restricted Stock Units. This indicates the sale was primarily a tax withholding event, not a discretionary open-market liquidation by the executive.

Does the filing mention any derivatives or options for James Winston King at Guidewire (GWRE)?

The filing’s derivative summary is empty, indicating no derivative transactions, such as stock options or similar instruments, were reported in this particular Form 4. The only reported activity involves non-derivative common stock tied to Restricted Stock Unit settlement.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 06/16/2026 - 08:06 PM EDT Learn about SEC filing dates

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^*

King James Winston

(Last) (First) (Middle)

C/O GUIDEWIRE SOFTWARE, INC.

970 PARK PL, SUITE 200

(Street)

SAN MATEO CALIFORNIA 94403

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Guidewire Software, Inc. [ GWRE ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Admin Officer, Gen Couns

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/16/2026

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

X	Form 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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	06/16/2026		S(1)		999	D	$118.743	31,702	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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

Remarks:

	/s/ James Winston King	06/16/2026
	** 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.
* Form 4: SEC 1474 (03-26)