Guidewire CEO sells 1,200 shares in planned trade

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of Common Stock.

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of Common Stock. The shares were sold at an average price of $158.92 per share. After this transaction, he directly holds 208,006 shares of Guidewire common stock.

The sale was executed pursuant to an automatic Rule 10b5-1 trading plan adopted by Rosenbaum on October 14, 2025, indicating the transaction was pre-scheduled rather than a discretionary trade.

Insider Trade Summary 10b5-1

Net Seller: 1,200 shares

Net Sell 1 txn

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,200 shs ($191K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,200	$158.92	$191K

Holdings After Transaction: Common Stock — 208,006 shares (Direct)

Footnotes (1)

1. F1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Key Figures

Shares sold: 1,200 shares Sale price per share: $158.92 per share Shares held after transaction: 208,006 shares +2 more

5 metrics

Shares sold 1,200 shares Open-market sale of Common Stock on June 1, 2026

Sale price per share $158.92 per share Average price for the 1,200 shares sold

Shares held after transaction 208,006 shares Direct ownership following the reported sale

Transaction code S Sale in open market or private transaction

10b5-1 plan adoption date October 14, 2025 Date CEO adopted the automatic trading plan

Key Terms

Rule 10b5-1 Trading Plan, open-market sale, Common Stock

3 terms

Rule 10b5-1 Trading Plan regulatory

"Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person"

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.

open-market sale financial

"transaction_action: "open-market sale" for the 1,200 shares of Common Stock"

An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.

Common Stock financial

"security_title: "Common Stock" and remaining direct holdings after the sale"

Common stock represents ownership shares in a company, giving investors a stake in its success and a say in important decisions through voting rights. It is the most common type of stock traded on markets and can provide income through dividends, as well as potential for value growth. For investors, holding common stock means sharing in the company’s profits and risks.

FAQ

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

What did Guidewire (GWRE) CEO Michael Rosenbaum report in this Form 4?

Guidewire CEO Michael Rosenbaum reported selling 1,200 shares of Common Stock in an open-market transaction. The sale was executed at an average price of $158.92 per share, under a pre-arranged Rule 10b5-1 trading plan adopted on October 14, 2025.

How many Guidewire (GWRE) shares did the CEO sell and at what price?

Michael Rosenbaum sold 1,200 shares of Guidewire Common Stock at an average price of $158.92 per share. This was an open-market sale, documented as a single non-derivative transaction on June 1, 2026, according to the Form 4 data.

How many Guidewire (GWRE) shares does the CEO still own after this sale?

After the reported sale, Michael Rosenbaum directly holds 208,006 shares of Guidewire Common Stock. This post-transaction holding figure comes from the Form 4 and reflects his remaining direct ownership following the 1,200-share disposition.

Was the Guidewire (GWRE) CEO’s stock sale under a Rule 10b5-1 plan?

Yes. The footnote states the sale was an automatic transaction under a Rule 10b5-1 Trading Plan. This plan was adopted by Michael Rosenbaum on October 14, 2025, indicating the timing of the trade was pre-scheduled rather than decided spontaneously.

What type of transaction did Guidewire (GWRE) report for its CEO?

The Form 4 shows a non-derivative open-market sale of Common Stock. The transaction code is “S,” described as a sale in an open market or private transaction, with 1,200 shares sold at $158.92 per share on June 1, 2026.

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

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Accepted by SEC EDGAR 06/02/2026 - 08:25 PM EDT 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^*

Rosenbaum Michael George

(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)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/01/2026

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	06/01/2026		S(1)		1,200	D	$158.92	208,006	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 14, 2025.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	06/02/2026
	** 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)