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

Yes. The filing states the sale was an automatic transaction under a Rule 10b5-1 trading plan adopted on October 14, 2025. Such plans pre-schedule trades, which can make the timing less indicative of the insider’s short-term market views.

Guidewire (GWRE) CEO 10b5-1 sale leaves 212,806 shares

Filing Impact

(High)

Filing Sentiment

(Negative)

Form Type

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 at $141.91 per share on May 4, 2026. The transaction was executed pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on October 14, 2025. Following this sale, Rosenbaum continues to hold 212,806 shares of Guidewire common stock directly.

Insider Trade Summary 10b5-1

Net Seller: 1,200 shares ($170,292)

Net Sell 1 txn

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,200 shs ($170K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,200	$141.91	$170K

Holdings After Transaction: Common Stock — 212,806 shares (Direct, null)

Footnotes (1)

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Key Figures

Shares sold: 1,200 shares Sale price per share: $141.91 per share Shares held after transaction: 212,806 shares +2 more

5 metrics

Shares sold 1,200 shares Open-market sale on May 4, 2026

Sale price per share $141.91 per share Guidewire common stock sale by CEO

Shares held after transaction 212,806 shares CEO’s direct holdings post-sale

Transaction code S Sale in open market or private transaction

Trading plan adoption date October 14, 2025 Rule 10b5-1 trading plan for automatic sales

Key Terms

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

4 terms

Rule 10b5-1 Trading Plan regulatory

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

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.

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.

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.

Form 4 Insider Transactions: What Each Field Means →

05/05/2026 - 06:29 AM

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

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)
05/04/2026

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)
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	05/04/2026		S⁽¹⁾		1,200	D	$141.91	212,806	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 14, 2025.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	05/05/2026
	** 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)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transaction did Guidewire (GWRE) disclose for its CEO?

Guidewire reported that CEO Michael George Rosenbaum sold 1,200 shares of common stock. The sale occurred on May 4, 2026 at $141.91 per share, and was executed as an open-market transaction under a pre-arranged Rule 10b5-1 trading plan.

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

The CEO sold 1,200 shares of Guidewire common stock at $141.91 per share. This was an open-market sale disclosed in a Form 4 filing, executed under a previously adopted Rule 10b5-1 trading plan for automated share sales.

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

After the reported transaction, CEO Michael George Rosenbaum directly holds 212,806 shares of Guidewire common stock. This figure reflects his remaining position following the 1,200-share open-market sale disclosed in the Form 4 insider trading report.

What type of security did the Guidewire (GWRE) CEO sell?

The CEO sold shares of Guidewire’s common stock. The Form 4 shows a single non-derivative transaction, describing it as an open-market or private-sale type transaction, with 1,200 common shares sold at a price of $141.91 per share.