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Guidewire Software Chief Executive Maintains Large Stake Despite Recent Sale

Filing Impact
(Moderate)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Guidewire Software CEO Michael George Rosenbaum reported two significant stock transactions:

  • On June 16, 2025, executed an automatic sale of 1,400 shares at $254.53 per share through a pre-established 10b5-1 Trading Plan from October 2024
  • On June 17, 2025, disposed of 5,925 shares at an average price of $248.94 to cover tax obligations related to Restricted Stock Unit settlement

Following these transactions, Rosenbaum directly owns 238,668 shares of Guidewire Software (GWRE). The sales were executed through standard insider trading compliance procedures, with the first transaction following an automated trading plan and the second addressing tax obligations. These transactions represent routine executive stock management rather than strategic investment decisions.

Positive

  • None.

Negative

  • None.
Insider Rosenbaum Michael George
Role Chief Executive Officer
Sold 7,325 shs ($1.83M)
Type Security Shares Price Value
Sale Common Stock 5,925 $248.938 $1.47M
Sale Common Stock 1,400 $254.53 $356K
Holdings After Transaction: Common Stock — 238,668 shares (Direct)
Footnotes (1)
  1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 15, 2024. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $248.9377 to $248.9386 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.
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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 CA 94403
(City) (State) (Zip)
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
3. Date of Earliest Transaction (Month/Day/Year)
06/16/2025
4. If Amendment, Date of Original Filed (Month/Day/Year)
 6. Individual or Joint/Group Filing (Check Applicable Line)
X Form filed by One Reporting Person
Form filed by More than One Reporting Person
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 06/16/2025 S(1) 1,400 D $254.53 244,593 D
Common Stock 06/17/2025 S(2) 5,925 D $248.938(3) 238,668 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 15, 2024.
2. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.
3. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $248.9377 to $248.9386 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.
Remarks:
By: Winston King, Attorney-in-Fact for Michael George Rosenbaum 06/18/2025
** 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.

Source: View Original Filing on SEC EDGAR

FAQ

How many GWRE shares did CEO Michael Rosenbaum sell on June 16, 2025?

CEO Michael Rosenbaum sold 1,400 shares of Guidewire Software (GWRE) at a price of $254.53 per share on June 16, 2025, through an automatic sale pursuant to a 10b5-1 Trading Plan adopted on October 15, 2024.

What was the purpose of GWRE CEO's stock sale on June 17, 2025?

The June 17, 2025 sale of 5,925 GWRE shares was conducted by the issuer to cover taxes associated with the settlement of Restricted Stock Units for CEO Michael Rosenbaum. The shares were sold at an average price ranging from $248.9377 to $248.9386 per share.

How many GWRE shares does CEO Michael Rosenbaum own after the June 2025 transactions?

Following the reported transactions, CEO Michael Rosenbaum directly owns 238,668 shares of Guidewire Software (GWRE) stock.

When did GWRE CEO Rosenbaum establish his 10b5-1 trading plan?

Michael Rosenbaum established his 10b5-1 Trading Plan on October 15, 2024, which governed the automatic sale of shares that occurred on June 16, 2025.

What positions does Michael Rosenbaum hold at GWRE according to the Form 4?

According to the Form 4, Michael Rosenbaum serves as both Chief Executive Officer and Director of Guidewire Software (GWRE).