Guidewire CEO awarded 45,906 performance shares

Guidewire’s CEO reported an automatic 10b5-1 sale of 1,200 shares and a new 45,906-share performance-based equity award.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) CEO and director Michael George Rosenbaum reported both a sale and equity awards. On September 14, 2026, he sold 1,200 shares of Common Stock at $145.87 per share in an automatic transaction pursuant to a Rule 10b5-1 Trading Plan adopted on October 14, 2025.

On September 11, 2026, he received a grant of 45,906 Performance Shares, each representing the right to receive one share of Common Stock, and a related non-derivative award for 45,906 shares of Common Stock. The Performance Shares cliff vest after a three-year performance period, based on average performance over three one-year measurement periods and continued employment through September 15, 2029, and expire on September 11, 2036.

Insider Trade Summary 10b5-1

Net Seller: 1,200 shares

Net Sell 3 txns

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,200 shs ($175K)

Type	Security	Shares	Price	Value
Sale	Common Stock F1	1,200	$145.87	$175K
Grant/Award	Performance Shares F2	45,906	$0.00	$0.00
Grant/Award	Common Stock	45,906	$0.00	$0.00

Holdings After Transaction: Performance Shares — 45,906 contracts (Direct); Common Stock — 230,082 shares (Direct)

Footnotes (2)

1. F1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.
2. F2. These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2029. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

Key Figures

Shares sold: 1,200 shares Sale price: $145.87 per share Performance Shares granted: 45,906 Performance Shares +3 more

6 metrics

Shares sold 1,200 shares Common Stock sale on September 14, 2026

Sale price $145.87 per share Common Stock sale on September 14, 2026

Performance Shares granted 45,906 Performance Shares Grant on September 11, 2026

Underlying Common Stock for Performance Shares 45,906 shares Each Performance Share corresponds to one share of Common Stock

Performance Shares expiration date September 11, 2036 Expiration of the Performance Shares award

Employment condition date September 15, 2029 Continued employment required through this date for vesting

Key Terms

Rule 10b5-1 Trading Plan, Performance Shares, cliff vest, performance period

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.

Performance Shares financial

"These Performance Shares cliff vest at the end of the three-year performance period"

Performance shares are a type of company stock given to executives or employees that only become theirs if the company meets specific goals, like hitting certain profits or growth targets. They motivate leaders to work toward the company’s success, because their additional shares depend on achieving these results.

cliff vest financial

"These Performance Shares cliff vest at the end of the three-year performance period"

A cliff vest is a schedule for stock options or restricted shares where no ownership rights are earned until a fixed date, after which a set portion becomes fully owned all at once — like a probation period that suddenly unlocks pay. Investors watch cliff vests because they influence when insiders can sell shares, affect staff retention and dilution timing, and help predict short-term changes in a company’s shareholder makeup.

performance period financial

"at the end of the three-year performance period based on the average performance"

The performance period is the specific time span over which an investment’s results, an employee’s targets, or a fund’s returns are measured and judged. It matters to investors because the length and start/end of that window determine which gains or losses count toward performance fees, bonus payouts, or benchmark comparisons—much like timing a race decides who wins, the chosen period can change whether results look strong or weak.

FAQ

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

What insider transactions did GWRE’s CEO report on this Form 4?

Michael George Rosenbaum reported selling 1,200 shares of Common Stock on September 14, 2026, and receiving grants totaling 45,906 Performance Shares and a related 45,906-share Common Stock award on September 11, 2026.

At what price did the GWRE CEO sell shares on September 14, 2026?

On September 14, 2026, the CEO sold 1,200 shares of Guidewire Common Stock at $145.87 per share in a sale described as occurring in the open market or a private transaction.

Was the GWRE CEO’s September 14, 2026 sale under a Rule 10b5-1 plan?

Yes. The sale of 1,200 shares on September 14, 2026 was an automatic sale pursuant to a Rule 10b5-1 Trading Plan that Michael George Rosenbaum adopted on October 14, 2025.

What are the terms of the 45,906 GWRE Performance Shares granted to the CEO?

The CEO received 45,906 Performance Shares on September 11, 2026. They cliff vest at the end of a three-year performance period, based on the average performance of three one-year periods and require continued employment through September 15, 2029, with expiration on September 11, 2036.

How many underlying GWRE common shares are tied to the Performance Shares grant?

The 45,906 Performance Shares granted on September 11, 2026 each correspond to one share of Guidewire Common Stock, for a total underlying amount of 45,906 shares of Common Stock.

Is the GWRE CEO a director as well as an officer in this filing?

Yes. The reporting person, Michael George Rosenbaum, is identified as both a director and an officer, serving as Chief Executive Officer of Guidewire Software, Inc.

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

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Available on EDGAR 09/14/2026 - 05:27 PM Accepted by SEC EDGAR 09/14/2026 - 05:26 PM 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)
09/11/2026

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	09/11/2026		A		45,906	A	$0	231,282	D
Common Stock	09/14/2026		S(1)		1,200	D	$145.87	230,082	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
Performance Shares	$0	09/11/2026		A		45,906		(2)	09/11/2036	Common Stock	45,906	$0	45,906	D

Explanation of Responses:

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

2. These Performance Shares cliff vest at the end of the three-year performance period based on the average performance of the three one-year performance periods and continued employment through September 15, 2029. One-year financial targets for each of the three performance measurement periods are set up front at the time of the grant.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	09/14/2026
	** 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)