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

Rhea-AI Filing Summary

Michael George Rosenbaum, CEO and Director of Guidewire Software (GWRE), reported insider transactions. On 09/11/2025 he was credited with 28,958 shares tied to Performance Shares at a reported price of $0, bringing his beneficial ownership to 250,826 shares. The filing notes these Performance Shares are subject to a three-year performance period with continued employment through September 15, 2028.

On 09/15/2025 an automatic sale under a 10b5-1 trading plan executed the disposition of 1,400 shares at $252.83, reducing his beneficial ownership to 249,426. The sale was reported by an attorney-in-fact on behalf of Rosenbaum.

Positive

• Performance-based compensation granted (28,958 Performance Shares) supports executive retention through September 15, 2028
• Sale executed under a 10b5-1 plan, which provides transparency that the disposition was prearranged

Negative

• Minor reduction in beneficial ownership of 1,400 shares following the sale on 09/15/2025

Insights

Corporate Governance Expert

TL;DR: Routine executive vesting and an automatic sale under a 10b5-1 plan; no material governance red flags in the filing.

The filing documents standard equity compensation mechanics: performance-based awards were recorded as acquired on 09/11/2025 and an automatic sale of a small portion of holdings occurred on 09/15/2025 under a pre-established 10b5-1 plan dated 10/15/2024. The Performance Shares include continued-employment vesting conditions through 09/15/2028, indicating multi-year retention incentives. Reporting was completed via attorney-in-fact, which is common practice for timely filings.

Securities Analyst

TL;DR: Transactions are operationally routine: vesting of performance awards and an automated disposition, with limited immediate market impact.

The net change in reported beneficial ownership is a decrease of 1,400 shares following the sale at $252.83, a small percentage relative to the reported stake (~249k shares). The 10b5-1 plan execution is explicitly noted, which clarifies the sale was preplanned rather than opportunistic. No additional derivative exercises or extraordinary transfers are reported.

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^*

Rosenbaum Michael George

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive Officer

3. Date of Earliest Transaction (Month/Day/Year)
09/11/2025

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	09/11/2025		A		28,958	A	$0	250,826	D
Common Stock	09/15/2025		S(1)		1,400	D	$252.83	249,426	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
Performance Shares	$0	09/11/2025		A		28,958		(2)	09/11/2035	Common Stock	28,958	$0	28,958	D

Explanation of Responses:

1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 15, 2024.

2. These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2028. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	09/15/2025
	** 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

What transactions did Guidewire (GWRE) insider Michael G. Rosenbaum report?

The filing reports acquisition of 28,958 Performance Shares on 09/11/2025 and an automatic sale of 1,400 shares on 09/15/2025 at $252.83 per share.

Why was the 1,400-share sale executed for GWRE insider Rosenbaum?

The sale was an automatic transaction pursuant to a 10b5-1 trading plan adopted by the reporting person on October 15, 2024.

How did these transactions change Rosenbaum's beneficial ownership in GWRE?

Beneficial ownership increased to 250,826 shares after the 09/11/2025 acquisition and decreased to 249,426 shares after the 09/15/2025 sale.

What are the vesting conditions for the Performance Shares reported?

The Performance Shares cliff vest at the end of a three-year performance period based on average performance of three one-year periods and continued employment through September 15, 2028.

Who filed the Form 4 on behalf of Michael G. Rosenbaum?

The Form 4 was submitted by Winston King, Attorney-in-Fact for Michael George Rosenbaum on 09/15/2025.