[144] Guidewire Software, Inc. SEC Filing

Rhea-AI Filing Summary

Guidewire Software (GWRE) Form 144 shows proposed sale of 7,149 shares of Common Stock through Morgan Stanley Smith Barney LLC on or about 09/16/2025. The filing reports an aggregate market value of $1,736,256.28 for those shares and lists total shares outstanding of 84,530,578. The shares were acquired as restricted stock units on 09/15/2025 as compensation and were recorded as acquired and paid on that date. The filer, identified as James Winston King, also disclosed sales totaling 4,511 shares in the prior three months with gross proceeds of $1,022,923.95. The notice includes the standard representation that the seller has no undisclosed material information.

Positive

• Compliant disclosure filed under Rule 144 listing broker, acquisition details, and recent sales
• Securities were acquired as compensation (RSUs), which is a common executive remuneration mechanism

Negative

• Proposed sale of 7,149 shares scheduled 09/16/2025 shortly after RSU acquisition on 09/15/2025
• Recent insider sales totaling 4,511 shares in the prior three months produced gross proceeds of $1,022,923.95

Insights

Securities Analyst

TL;DR: Insider plans a modest sale of newly vested RSUs; recent sales generated about $1.02M in proceeds.

The filing documents a proposed sale of 7,149 shares by an insider through Morgan Stanley Smith Barney with an aggregate reported market value of $1,736,256.28. The shares were acquired as restricted stock units on 09/15/2025 and the sale is scheduled approximately one day later, 09/16/2025. Prior dispositions by the same person over the past three months total 4,511 shares for gross proceeds of $1,022,923.95. From a trading-impact perspective, the sizes are small relative to the company's 84.5M shares outstanding, suggesting limited market impact but notable insider liquidity activity.

Corporate Governance Expert

TL;DR: Filing meets Rule 144 disclosure; rapid sale after RSU acquisition underscores insider liquidity but raises timing questions.

The Form 144 disclosure is complete in listing acquisition dates, nature of acquisition (restricted stock units), broker, and prior sales within three months. The filing includes the mandatory representation regarding material nonpublic information. Governance considerations center on the proximity between RSU acquisition (09/15/2025) and the proposed sale (09/16/2025); while permitted, such timing may draw shareholder attention to insider selling patterns rather than strategic voting or retention.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common Stock	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 38th Floor New York NY 10004	7149	1736256.28	84530578	09/16/2025	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	09/15/2025	Acquired as compensation - Restricted Stock Units	Issuer			7149	09/15/2025	N/A (acquired as compensation)

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	08/18/2025	799	169076.39
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/14/2025	1683	371353.95
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/14/2025	564	124446.6
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/14/2025	122	26919.3
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	07/14/2025	113	24933.45
James Winston King c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/17/2025	1230	306194.26

144: Remarks and Signature

Remarks

Date of Notice

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does the Form 144 filed for GWRE disclose?

The filing discloses a proposed sale of 7,149 shares of Guidewire Software common stock through Morgan Stanley Smith Barney and prior sales in the past three months.

When were the shares to be sold acquired?

The 7,149 shares were acquired as restricted stock units on 09/15/2025 and are listed as paid/acquired on that date.

How much are the proposed 7,149 shares reported to be worth?

The aggregate market value is $1,736,256.28 as reported in the Form 144.

How many shares did the filer sell in the past three months and for how much?

The filer sold 4,511 shares in the prior three months for gross proceeds totaling $1,022,923.95.

Through which broker is the sale proposed?

Morgan Stanley Smith Barney LLC Executive Financial Services is listed as the broker on the Form 144.