[Form 4] Guidewire Software, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Reporting person: James Winston King, Chief Administrative Officer and General Counsel of Guidewire Software, Inc. (GWRE).

On 09/18/2025 the reporting person executed a series of automatic sales under a 10b5-1 trading plan adopted October 15, 2024 and amended April 14, 2025. Four separate sale entries show dispositions of 1,878, 1,197, 1,940 and 2,147 shares, a total of 7,162 shares sold. Reported average sale prices for the blocks ranged approximately from $246.58 to $250.505 per share as described in the explanatory footnotes. The Form 4 shows the reporting person’s beneficial holdings declining across the transactions from 43,899 shares to 38,615 shares following the last sale. The Form is signed and dated 09/22/2025.

Positive

• Sales executed under a 10b5-1 trading plan, indicating the trades were prearranged and not ad-hoc
• Form 4 timely discloses per-block share counts, average price ranges, and post-transaction beneficial ownership

Negative

• Reporting person disposed of 7,162 shares on 09/18/2025, reducing beneficial ownership from 43,899 to 38,615 shares
• Average sale prices span a range (approximately $246.58 to $250.505), requiring per-price detail for full reconciliation (available on request)

Insights

Financial Analyst

TL;DR: Insider executed planned sales of 7,162 GWRE shares under an established 10b5-1 plan; transactions reported on Form 4.

The disclosed transactions are routine insider dispositions executed pursuant to a documented 10b5-1 trading plan adopted in October 2024 and amended in April 2025. The sales occurred on 09/18/2025 in four blocks, reducing beneficial ownership from 43,899 to 38,615 shares. Average prices reported across the blocks fall roughly in the $246.58 to $250.51 range per the explanatory notes. From a financial analysis standpoint, these are compliance-driven sales rather than ad-hoc insider trades; the Form 4 provides per-block share counts, ranges of sale prices, and post-transaction ownership, enabling clear reconciliation of the reported activity.

Corporate Governance Expert

TL;DR: Transactions were conducted under a 10b5-1 plan and properly disclosed on Form 4, indicating procedural compliance.

The filing documents that the trades were automatic sales under a 10b5-1 plan, which supports an affirmative defense to insider trading allegations when the plan terms are met. The Form 4 includes explanatory footnotes stating average sale-price ranges per block and notes that detailed per-price breakdowns are available upon request, which aligns with transparent disclosure practices. The signature and date are included, and the reporting person’s title is identified, satisfying the Form 4 disclosure requirements.

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 CA 94403

(City) (State) (Zip)

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

3. Date of Earliest Transaction (Month/Day/Year)
09/18/2025

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	09/18/2025		S(1)		1,878	D	$247.209(2)	43,899	D
Common Stock	09/18/2025		S(1)		1,197	D	$248.1553(3)	42,702	D
Common Stock	09/18/2025		S(1)		1,940	D	$249.3535(4)	40,762	D
Common Stock	09/18/2025		S(1)		2,147	D	$250.1226(5)	38,615	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. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 15, 2024, as amended on April 14, 2025.

2. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $246.5800 to $247.5600 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. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $247.7450 to $249.5900 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.

4. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $248.9000 to $249.8600 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.

5. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $249.1226 to $250.5050 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.

Remarks:

	/s/ James Winston King	09/22/2025
	** 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

How many GWRE shares did James Winston King sell on 09/18/2025?

He sold a total of 7,162 shares across four transactions (1,878; 1,197; 1,940; 2,147).

Were the sales by the GWRE insider part of a trading plan?

Yes. The sales were automatic dispositions pursuant to a 10b5-1 trading plan adopted October 15, 2024 and amended April 14, 2025.

What price ranges were reported for the GWRE share sales?

The explanatory notes report average sale-price ranges across the blocks approximately from $246.58 to $250.505 per share, with more granular per-price details available upon request.

How did the insider’s beneficial ownership change after the transactions?

Post-transaction beneficial ownership is reported as 38,615 shares following the last sale, down from 43,899 shares in the first reported line.

Who signed the Form 4 and when?

The Form 4 is signed by /s/ James Winston King and dated 09/22/2025.