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

Guidewire Software, Inc. (NYSE: GWRE) CEO sells 1,200 shares in 10b5-1 plan trade

Filing Impact
(High)
Filing Sentiment
(Negative)
Form Type
4

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum sold 1,200 shares of Common Stock on July 27, 2026 at $142.31 per share in an open-market or private transaction. The sale was executed automatically under a 10b5-1 trading plan adopted on October 14, 2025, leaving him with 192,576 directly held shares.

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Insider Rosenbaum Michael George
Role Chief Executive Officer
Sold 1,200 shs ($171K)
Type Security Shares Price Value
Sale Common Stock F1 1,200 $142.31 $171K
Holdings After Transaction: Common Stock — 192,576 shares (Direct)
Footnotes (1)
  1. F1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.
Shares sold 1,200 shares Common Stock sold by the CEO on July 27, 2026
Sale price per share $142.31 per share Price for the 1,200 shares of Common Stock sold
Shares held after sale 192,576 shares Directly held Common Stock following the July 27, 2026 sale
10b5-1 plan adoption date October 14, 2025 Date the CEO adopted the 10b5-1 Trading Plan used for this sale
10b5-1 Trading Plan regulatory
"Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person"
A 10b5-1 trading plan is a pre-arranged strategy that allows company insiders to buy or sell company stock at set times, regardless of their current knowledge about the company's situation. It acts like a scheduled appointment for trading, helping prevent the appearance of impropriety or insider trading. This plan provides a way for insiders to sell or buy shares in a controlled, transparent manner, offering reassurance to investors about fair trading practices.
open market or private transaction financial
"transaction code description states Sale in open market or private transaction"
Chief Executive Officer financial
"Rosenbaum Michael George is listed with officer title Chief Executive Officer"
A chief executive officer (CEO) is the top leader of a company, responsible for making major decisions, setting goals, and guiding the organization’s overall direction. Think of the CEO as the captain of a ship, steering it toward success. Investors pay close attention to the CEO because their leadership and strategy can significantly influence the company's performance and future growth.

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

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Form 4 Insider Transactions: What Each Field Means →

FAQ

What insider transaction did GWRE report in this Form 4?
Guidewire’s CEO Michael George Rosenbaum sold 1,200 shares of Common Stock on July 27, 2026 at $142.31 per share. The transaction was an open-market or private sale and was executed automatically under a pre-established 10b5-1 trading plan.

How many GWRE shares does the CEO hold after this sale?
After the reported transaction, the CEO directly holds 192,576 shares of Guidewire Common Stock. This figure reflects his position following the July 27, 2026 sale of 1,200 shares executed under an automatic 10b5-1 trading plan.

Was the GWRE CEO’s share sale made under a 10b5-1 trading plan?
Yes, the 1,200-share sale was an automatic transaction under a 10b5-1 Trading Plan. The plan was adopted by the CEO on October 14, 2025, and governs how and when these preset sales occur.

What price did the GWRE CEO receive per share in this transaction?
The CEO’s 1,200-share sale of Guidewire Common Stock was executed at $142.31 per share. The filing describes it as a sale in an open-market or private transaction, with the price reported on a per-share basis.

Who is the insider involved in the latest GWRE Form 4 filing?
The insider is Michael George Rosenbaum, Guidewire Software, Inc.’s Chief Executive Officer and a director. He reported selling 1,200 shares of Common Stock on July 27, 2026 under an automatic 10b5-1 trading plan.
SEC Form 4
FORM 4UNITED 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)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
Chief Executive Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
07/27/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm 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)
CodeVAmount(A) or (D)Price
Common Stock07/27/2026S(1)1,200D$142.31192,576D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount 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 Rosenbaum07/27/2026
** Signature of Reporting PersonDate
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