Guidewire CEO sells 1,200 shares in planned trade

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

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum sold 1,200 shares of Common Stock in an open-market transaction. The shares were sold at an average price of $138.09 per share and were executed automatically under a Rule 10b5-1 Trading Plan adopted by Rosenbaum on October 14, 2025.

After this sale, Rosenbaum directly holds 214,006 shares of Guidewire Software, Inc. common stock, so the transaction represents a small portion of his overall reported holdings.

Insights

Equity ownership and insider-trading analyst

CEO sale is small, pre-planned under a 10b5-1 plan, and appears routine.

The filing shows CEO Michael George Rosenbaum completed an open-market sale of 1,200 shares of Guidewire Software, Inc. common stock at $138.09 per share. The transaction is coded as an open-market sale and is clearly labeled as such.

A key detail is the footnote stating the sale occurred automatically under a Rule 10b5-1 Trading Plan adopted on October 14, 2025. Such plans are pre-arranged, reducing the informational content of timing. Rosenbaum retains 214,006 shares after the sale, so this is a small fraction of his disclosed position.

Based on the small relative size and pre-planned nature, this transaction looks like routine portfolio management rather than a major shift in insider sentiment. Future company filings may provide additional context if his ownership changes materially over time.

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 ($166K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,200	$138.09	$166K

Holdings After Transaction: Common Stock — 214,006 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: $138.09 per share Shares held after transaction: 214,006 shares +1 more

4 metrics

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

Sale price per share $138.09 per share Average price for the 1,200 shares sold

Shares held after transaction 214,006 shares CEO direct ownership following the sale

10b5-1 plan adoption date October 14, 2025 Date CEO adopted Rule 10b5-1 Trading Plan

Key Terms

Rule 10b5-1 Trading Plan, open-market sale, Form 4, Common Stock

4 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""

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.

Form 4 regulatory

"INSIDER FILING DATA (Form 4)"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

Common Stock financial

"security_title: "Common Stock""

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 insider transaction did Guidewire (GWRE) report for its CEO?

Guidewire reported that CEO Michael George Rosenbaum sold 1,200 shares of Common Stock. The shares were sold in an open-market transaction at an average price of $138.09 per share, as disclosed in a Form 4 insider trading report filed with regulators.

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

After the reported sale, CEO Michael George Rosenbaum directly holds 214,006 shares of Guidewire Software, Inc. common stock. This indicates the 1,200 shares sold represent a small portion of his reported ownership position in the company following the transaction.

Was the Guidewire (GWRE) CEO’s stock sale part of a 10b5-1 trading plan?

Yes. A footnote explains the 1,200-share sale was executed automatically under a Rule 10b5-1 Trading Plan adopted by CEO Michael George Rosenbaum on October 14, 2025, indicating the transaction was pre-arranged rather than timed discretionarily.

What price did the Guidewire (GWRE) CEO receive for the shares sold?

The Form 4 filing states that CEO Michael George Rosenbaum’s 1,200 shares of Guidewire common stock were sold at an average price of $138.09 per share. This reflects the per-share transaction price for the open-market sale reported in the filing.

Does this Guidewire (GWRE) insider sale appear large relative to the CEO’s holdings?

The sale appears relatively small compared with the CEO’s remaining stake. He sold 1,200 shares but still directly owns 214,006 shares of Guidewire common stock, suggesting this transaction represents only a minor reduction in his disclosed holdings.

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

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Accepted by SEC EDGAR 04/27/2026 - 04:32 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)
04/27/2026

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	04/27/2026		S(1)		1,200	D	$138.09	214,006	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	04/27/2026
	** 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)