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

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported selling a total of 7,030 shares of common stock in mid-June 2026. The transactions occurred on June 15 and June 16 at prices between $118.743 and $123.85 per share.

After these sales, Rosenbaum continues to hold 199,776 shares of Guidewire common stock directly. Footnotes state that the activity included an automatic sale under a Rule 10b5-1 trading plan and sales by the issuer to cover taxes associated with settlement of Restricted Stock Units.

Insider Trade Summary 10b5-1

Net Seller: 7,030 shares ($840,892)

Net Sell 2 txns

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 7,030 shs ($841K)

Type	Security	Shares	Price	Value
Sale	Common Stock	5,830	$118.743	$692K
Sale	Common Stock	1,200	$123.85	$149K

Holdings After Transaction: Common Stock — 199,776 shares (Direct, null)

Footnotes (1)

1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

Key Figures

Total shares sold: 7,030 shares Shares sold on June 16, 2026: 5,830 shares at $118.743 Shares sold on June 15, 2026: 1,200 shares at $123.85 +2 more

5 metrics

Total shares sold 7,030 shares Net insider sales reported in this Form 4

Shares sold on June 16, 2026 5,830 shares at $118.743 Open-market sale of common stock

Shares sold on June 15, 2026 1,200 shares at $123.85 Open-market sale of common stock

Shares held after transactions 199,776 shares Direct ownership following June 16, 2026 sale

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

Key Terms

Rule 10b5-1 Trading Plan, Restricted Stock Units, open-market sale, 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.

Restricted Stock Units financial

"Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units."

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

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

"Net insider sales reported in this 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.

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Form 4 Insider Transactions: What Each Field Means →

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)
06/15/2026

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	06/15/2026		S(1)		1,200	D	$123.85	205,606	D
Common Stock	06/16/2026		S(2)		5,830	D	$118.743	199,776	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.

2. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	06/16/2026
	** 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)