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

Rhea-AI Filing Summary

Michael George Rosenbaum, Guidewire Software CEO and director, reported an automatic sale of 1,400 shares of Guidewire common stock on 10/06/2025 at a price of $230.08 per share. The filing shows 260,758 shares beneficially owned following the transaction. The sale was executed under a 10b5-1 trading plan that the reporting person adopted on 10/15/2024, and the Form 4 was signed by an attorney-in-fact on 10/06/2025. The filing discloses a routine insider sale using a pre-established plan rather than an ad-hoc transaction.

Positive

• Sale executed under a 10b5-1 trading plan adopted on 10/15/2024, which supports pre-planned execution
• Filing discloses post-transaction holdings of 260,758 shares, maintaining transparency

Negative

• Officer and director completed a sale of 1,400 shares, which reduces direct ownership
• Single-line sale provides limited context about broader insider selling or plan schedule

Insights

Insider Transactions Analyst

TL;DR: A routine, pre-planned insider sale of 1,400 shares at $230.08 under a 10b5-1 plan.

The reporting person, serving as CEO and director, recorded a sale of 1,400 shares on 10/06/2025 at $230.08 per share. The filing explicitly states the sale was automatic under a 10b5-1 trading plan adopted on 10/15/2024, which provides an affirmative defense for planned transactions.

Reliance on a 10b5-1 plan reduces concerns about opportunistic timing, but the transaction still reduces the officer's direct holdings to 260,758 shares. Watch for additional Form 4s near typical plan execution dates for pattern confirmation within the next 12 months.

Corporate Governance Advisor

TL;DR: Use of a documented trading plan aligns with standard governance practices for insiders.

The record shows the sale was processed via a documented plan and signed by an attorney-in-fact, indicating procedural compliance with Section 16 reporting and Rule 10b5-1 conditions. The filing includes the required explanatory remark noting the plan adoption date.

Governance watchers may note the combination of officer and director status when assessing insider activity; any further scheduled sales under the same plan or amendments would be relevant over the coming year.

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)
10/06/2025

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	10/06/2025		S(1)		1,400	D	$230.08	260,758	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.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	10/06/2025
	** 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 did Guidewire CEO Michael G. Rosenbaum sell (GWRE)?

The CEO sold 1,400 shares of Guidewire common stock on 10/06/2025 at $230.08 per share.

Was the sale by the GWRE reporting person planned?

Yes. The sale was automatic under a 10b5-1 trading plan adopted on 10/15/2024, as stated in the Form 4.

How many Guidewire shares does the reporting person own after the sale?

The Form 4 reports 260,758 shares beneficially owned following the reported transaction.

Who signed the Form 4 for Michael G. Rosenbaum?

The Form 4 was signed by Winston King, Attorney-in-Fact for Michael George Rosenbaum on 10/06/2025.

Does the Form 4 indicate any option exercises or derivative transactions?

No. The filing shows a non-derivative sale of common stock; Table II (derivatives) contains no reported transactions.