Guidewire Software Inc SEC Filings

A shareholder has filed a notice to sell 1,200 shares of common stock through Morgan Stanley Smith Barney under Rule 144. The shares have an aggregate market value of $217,044.00, with the issuer reporting 85,019,176 shares outstanding and an approximate sale date of 01/13/2026 on the NYSE. The securities were acquired as performance shares on 09/15/2022 directly from the issuer, with the same date listed as payment. The filing also lists multiple prior sales of common shares by Mike Rosenbaum over the past three months, including several transactions of 1,400 shares and one transaction of 6,015 shares, all with disclosed gross proceeds.

Guidewire Software, Inc. disclosed that its board has approved a new share repurchase program authorizing the company to buy back up to $500.0 million of its common stock. The company has fully completed its prior repurchase program that was authorized in September 2022, after using the remaining $138.2 million under that plan.

Repurchases may occur over time in the open market, through privately negotiated deals or other methods, and can be executed under Rule 10b-18 and potential Rule 10b5-1 trading plans. The program is discretionary, can be modified or terminated at any time, and does not require the company to repurchase a specific amount.

Guidewire expects to fund any buybacks using existing cash and cash equivalents, working capital or cash flows from operations. As of October 31, 2025, the company reported cash, cash equivalents and investments totaling $1,409.3 million, providing substantial resources to support the new authorization.

Guidewire Software, Inc. Chief Executive Officer and Director Michael George Rosenbaum reported a sale of company stock. On 12/29/2025, he sold 1,400 shares of common stock at a price of $204.95 per share in a transaction coded "S" for sale. After this transaction, he beneficially owned 237,943 shares of Guidewire common stock in direct ownership.

The filing notes that this was an automatic sale made under a Rule 10b5-1 trading plan that Rosenbaum adopted on October 15, 2024, which is a pre-arranged plan designed to allow insiders to sell shares over time according to set instructions.

Mike Rosenbaum filed a notice of proposed sale under Rule 144 to sell 1,400 shares of common stock through Morgan Stanley Smith Barney on the NYSE, with an aggregate market value of $286,930.00. The filing states that these shares were acquired as performance shares from the issuer on 09/15/2022, with payment also dated that day and described as not applicable for cash terms.

Over the past three months, the notice lists a series of prior sales of the issuer’s common stock by Mike Rosenbaum, including 6,015 shares sold on 12/16/2025 for gross proceeds of $1,155,337.74, along with multiple 1,400‑share transactions on various dates. The issuer reports 85,019,176 shares of this class outstanding.

Guidewire Software, Inc. Chief Executive Officer and director Michael George Rosenbaum sold 1,400 shares of common stock on December 22, 2025 at $200.72 per share. Following this transaction, he beneficially owned 239,343 shares directly. The sale was described as an automatic transaction carried out under a Rule 10b5-1 trading plan that he adopted on October 15, 2024, which allows preset, scheduled sales of company stock by insiders.

This notice reports a planned sale under Rule 144 of 1,400 shares of common stock of the issuer through Morgan Stanley Smith Barney LLC, with an aggregate market value of $281,008.00. The shares are to be sold on the NYSE around 12/22/2025, and the filing notes that 85,019,176 shares of this class were outstanding. The 1,400 shares were acquired on 09/15/2022 as performance shares from the issuer, with payment noted as not applicable. The form also lists multiple prior common stock sales over the past three months by the same seller, including a transaction of 6,015 shares on 12/16/2025 for $1,155,337.74.

Guidewire Software, Inc. reported the results of its 2025 annual meeting of stockholders held on December 15, 2025. A quorum was present, with 79,780,871 shares of common stock represented in person or by proxy.

Stockholders elected eight directors, including Michael C. Keller and Mike Rosenbaum, each to serve a one-year term expiring at the 2026 annual meeting and until a successor is elected and qualified. Stockholders also ratified the appointment of KPMG LLP as independent registered public accounting firm for the fiscal year ending July 31, 2026, with 79,400,946 votes for, 320,826 against and 59,099 abstentions.

In addition, stockholders approved, on a non-binding advisory basis, the compensation of the company’s named executive officers, with 73,326,214 votes for, 1,447,631 against and 64,517 abstentions. There were 4,942,509 broker non-votes on each of the director and executive compensation proposals, and no other items were presented for approval.

A holder of the issuer’s common stock has filed a notice to sell shares under Rule 144. The planned transaction covers 1,232 common shares to be sold through Morgan Stanley Smith Barney LLC on the NYSE, with an aggregate market value of 240,240.00. The issuer has 85,019,176 common shares outstanding.

The shares being sold were acquired as restricted stock from the issuer on 12/15/2025. The filer previously sold 2,872 common shares on 12/16/2025, generating gross proceeds of 551,642.56 over the past three months. By signing the notice, the seller represents that they are not aware of any material adverse information about the issuer’s current or prospective operations that has not been publicly disclosed.

James King filed a Rule 144 notice to sell 1,860 shares of GWRE common stock through Morgan Stanley Smith Barney LLC Executive Financial Services on the NYSE, with an approximate sale date of 12/18/2025 and an aggregate market value of 362700.00.

The shares to be sold were acquired from the issuer as restricted stock and performance shares in several grants dated 03/15/2021, 12/15/2021, 03/15/2021 and 12/15/2025.

During the past three months, James King has also sold common shares in three transactions of 1,457, 798 and 798 shares, generating gross proceeds of 279854.88, 177586.92 and 196068.60.