Guidewire counsel sells 13,195 shares in Sept.

Guidewire’s Chief Admin Officer and General Counsel reported 13,195 shares disposed in September 2026, including tax-cover sales and an automatic Rule 10b5-1 trade.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) reports that Chief Admin Officer and General Counsel James Winston King had a net disposition of 13,195 shares of Common Stock in mid-September 2026. On September 17, 2026, 11,814 shares were sold by the issuer to cover taxes from Restricted Stock Unit settlement at an average price of $144.4713 per share, based on individual trades between $144.4695 and $144.4714. On September 18, 2026, 1,381 shares were sold at $144.98 per share in an open-market or private transaction, described as an automatic sale under a Rule 10b5-1 Trading Plan adopted on October 14, 2025 and amended on April 9, 2026.

Insider Trade Summary 10b5-1

Net Seller: 13,195 shares

Net Sell 2 txns

Insider King James Winston

Role Chief Admin Officer, Gen Couns

Sold 13,195 shs ($1.91M)

Type	Security	Shares	Price	Value
Sale	Common Stock F3	1,381	$144.98	$200K
Sale	Common Stock F1, F2	11,814	$144.4713	$1.71M

Holdings After Transaction: Common Stock — 44,558 shares (Direct)

Footnotes (3)

1. F1. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.
2. F2. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4695 to $144.4714 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.
3. F3. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended on April 9, 2026.

Key Figures

Total shares disposed: 13,195 shares Tax-cover sale shares: 11,814 shares Automatic 10b5-1 sale shares: 1,381 shares +5 more

8 metrics

Total shares disposed 13,195 shares Net shares sold by the reporting officer in September 2026

Tax-cover sale shares 11,814 shares Shares sold by issuer on September 17, 2026 to cover RSU-related taxes

Automatic 10b5-1 sale shares 1,381 shares Shares sold on September 18, 2026 under a Rule 10b5-1 Trading Plan

Average price for tax-cover sale $144.4713 per share Weighted average sale price on September 17, 2026

Price range for tax-cover sale $144.4695–$144.4714 per share Range of individual sale prices on September 17, 2026

Price for 10b5-1 sale $144.98 per share Sale price for 1,381 shares on September 18, 2026

Rule 10b5-1 plan adoption date October 14, 2025 Adoption date of trading plan governing the September 18, 2026 sale

Rule 10b5-1 plan amendment date April 9, 2026 Amendment date of the trading plan referenced for the automatic sale

Key Terms

Restricted Stock Units, Rule 10b5-1 Trading Plan, average sale price, open market or private transaction

4 terms

Restricted Stock Units financial

"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.

Rule 10b5-1 Trading Plan regulatory

"Automatic sale pursuant to a 10b5-1 Trading Plan adopted"

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

average sale price financial

"represents the average sale price of the shares sold ranging"

open market or private transaction financial

"Sale in open market or private transaction"

FAQ

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

What insider transactions did GWRE report for James Winston King in this Form 4?

The filing reports two dispositions totaling 13,195 shares of Guidewire Software, Inc. Common Stock in September 2026: 11,814 shares on September 17, 2026 and 1,381 shares on September 18, 2026.

Were the GWRE insider sales by James Winston King made under a Rule 10b5-1 plan?

Yes. The Form 4 indicates transactions under a Rule 10b5-1 trading plan, and the September 18, 2026 sale of 1,381 shares is described as an automatic sale pursuant to a 10b5-1 Trading Plan adopted October 14, 2025 and amended April 9, 2026.

How many GWRE shares were sold to cover taxes from RSU settlement?

On September 17, 2026, 11,814 shares of Guidewire Software, Inc. Common Stock were sold by the issuer to cover taxes associated with settlement of Restricted Stock Units for James Winston King.

What prices were received in the GWRE insider sales reported?

The September 17, 2026 tax-cover sale averaged $144.4713 per share, based on sales between $144.4695 and $144.4714. The September 18, 2026 automatic sale of 1,381 shares occurred at $144.98 per share.

What is the role of James Winston King at Guidewire Software (GWRE)?

James Winston King is reported as an officer of Guidewire Software, Inc., holding the title Chief Admin Officer, Gen Couns (Chief Administrative Officer and General Counsel).

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

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Available on EDGAR 09/21/2026 - 05:23 PM Accepted by SEC EDGAR 09/21/2026 - 05:23 PM 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).

X

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)
09/17/2026

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	09/17/2026		S(1)		11,814	D	$144.4713(2)	45,939	D
Common Stock	09/18/2026		S(3)		1,381	D	$144.98	44,558	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.

2. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4695 to $144.4714 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

3. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended on April 9, 2026.

Remarks:

	/s/ James Winston King	09/21/2026
	** 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)