[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Form 144 Overview – Guidewire Software, Inc. (GWRE)

Mike Rosenbaum has filed a Form 144 indicating an intent to sell 1,400 shares of GWRE common stock on or after 23 June 2025. The proposed shares represent roughly 0.0017 % of the 84.2 million shares outstanding and have an aggregate market value of $333,368 (≈ $238 per share). Morgan Stanley Smith Barney LLC will act as broker and the sale is expected to occur on the NYSE.

Acquisition background: The securities to be sold were received as performance shares on 15 September 2021 directly from the issuer. No alternative consideration was paid.

Recent selling activity: The filer reports 21 separate open-market sales over the past three months, totaling ≈24,125 shares and generating approximately $6.4 million in gross proceeds. Transaction sizes ranged from 45 to 5,925 shares and prices appear to have averaged in the mid-$200 range.

This filing is a notice only; it does not itself consummate the transaction. The signer affirms no undisclosed material adverse information and acknowledges Rule 10b5-1 representations.

Positive

• Regulatory compliance: The filer is adhering to Rule 144 notice requirements and references 10b5-1 safeguards.
• Minimal dilution/control impact: 1,400 shares (~0.0017 % of outstanding) are immaterial to share count and voting power.

Negative

• Continuing insider sales: Approximately 24,125 shares sold over the past three months, indicating sustained selling pressure from the same account.
• Potential sentiment drag: Investors may interpret recurrent insider disposals as a lack of confidence in near-term upside.

Insights

Securities Analyst

TL;DR Continued insider selling signals modest negative sentiment but volume is immaterial versus float.

Form 144 filings typically precede discretionary or 10b5-1 plan sales by affiliates. While the incremental 1,400-share sale is negligible relative to Guidewire’s 84 million-share float, the cumulative 24 k shares sold since late March (~0.03 % of shares outstanding) suggests the seller is consistently monetising equity at current price levels. Investors often view persistent insider selling as a mild head-wind for near-term sentiment, particularly when unaccompanied by offsetting insider purchases. However, the small proportion and the performance-share origin lessen dilution or governance concerns. Impact is therefore modestly negative but not fundamentally material.

Corporate Governance Expert

TL;DR Filing is routine, shows compliance with Rule 144; risk profile unchanged.

Rule 144 requires affiliates to notify the SEC when sales exceed certain thresholds. The disclosure demonstrates procedural adherence and transparency. The use of a large broker and explicit 10b5-1 language lowers litigation or perception risks. Given the fractional stake involved, corporate control and voting dynamics remain unaffected. From a governance standpoint, the transaction is not impactful; it simply converts earned performance shares into cash within allowed trading windows.

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

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	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	1400	333368.00	84195223	06/23/2025	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	09/15/2021	Performance Shares	ISSUER			1400	09/15/2021	Not Applicable

* 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
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/17/2025	5925	1474957.84
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/16/2025	1400	356342.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/09/2025	45	11542.50
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/09/2025	1355	347557.50
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/02/2025	1400	301490.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/27/2025	534	113218.68
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/27/2025	866	183609.32
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/19/2025	1000	215250.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/19/2025	400	86100.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/12/2025	1400	303114.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	05/05/2025	1400	291704.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/28/2025	932	184741.04
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/28/2025	468	92766.96
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/21/2025	652	123514.88
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/21/2025	748	141701.12
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/14/2025	1400	272860.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/07/2025	1169	196181.58
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	04/07/2025	231	38766.42
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	03/31/2025	366	67494.06
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	03/31/2025	1034	190679.94
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	03/24/2025	1400	273210.00

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

How many GWRE shares does the Form 144 cover?

The notice covers 1,400 common shares with an aggregate market value of $333,368.

When can the GWRE shares be sold?

The approximate sale date disclosed is 23 June 2025 on the NYSE.

What prior GWRE sales has the filer made recently?

The filer reports 21 sales in the last three months totaling ≈24,125 shares and about $6.4 million in proceeds.

Were the GWRE shares purchased or granted?

They were performance shares granted on 15 September 2021; no cash purchase price was paid.

Who is the broker executing the GWRE trade?

The broker of record is Morgan Stanley Smith Barney LLC, Executive Financial Services, New York.