Guidewire Software CEO Maintains Strong Position Despite Automated Stock Sale

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Rhea-AI Filing Summary

Guidewire Software CEO Michael George Rosenbaum reported the sale of 1,400 shares of common stock at a price of $238.12 per share on June 23, 2025. The transaction was executed as part of a pre-planned 10b5-1 trading plan established on October 15, 2024.

Following the transaction, Rosenbaum continues to hold 237,268 shares directly. The sale represents a small portion of his total holdings, approximately 0.6% of his position. The transaction was automatically executed under the trading plan, which helps executives avoid accusations of insider trading by establishing predetermined trading parameters.

Key Transaction Details:

Transaction Type: Automatic sale under 10b5-1 plan
Total Transaction Value: Approximately $333,368
Position: CEO and Director
Ownership Form: Direct

Insider Trade Summary

Net Seller: 1,400 shares

Net Sell 1 txn

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,400 shs ($333K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,400	$238.12	$333K

Holdings After Transaction: Common Stock — 237,268 shares (Direct)

Footnotes (1)

F1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 15, 2024.

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Form 4 Insider Transactions: What Each Field Means →

Accepted by SEC EDGAR 06/23/2025 - 08:30 PM

FAQ

How many GWRE shares did CEO Michael Rosenbaum sell on June 23, 2025?

CEO Michael Rosenbaum sold 1,400 shares of Guidewire Software (GWRE) common stock at a price of $238.12 per share on June 23, 2025.

How many GWRE shares does Michael Rosenbaum own after his June 2025 transaction?

Following the reported transaction, Michael Rosenbaum directly owns 237,268 shares of Guidewire Software (GWRE) common stock.

Was GWRE CEO Rosenbaum's stock sale part of a pre-planned trading arrangement?

Yes, the sale was executed as an automatic sale pursuant to a 10b5-1 Trading Plan that was previously adopted by Rosenbaum on October 15, 2024.

What positions does Michael Rosenbaum hold at GWRE as of June 2025?

Michael Rosenbaum serves as both the Chief Executive Officer and a Director of Guidewire Software (GWRE).

What was the total value of GWRE shares sold by CEO Rosenbaum in June 2025?

CEO Rosenbaum sold 1,400 shares at $238.12 per share, for a total transaction value of $333,368.

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^*

Rosenbaum Michael George

(Last)

(First)

(Middle)

C/O GUIDEWIRE SOFTWARE, INC.

970 PARK PL, SUITE 200

(Street)

SAN MATEO

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)
06/23/2025

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	06/23/2025		S⁽¹⁾		1,400	D	$238.12	237,268	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

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	06/23/2025
	** 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.

Source: View Original Filing on SEC EDGAR