GUIDEWIRE SOFTWARE (GWRE) Form 4 Filings

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of common stock on April 13, 2026 at $118.77 per share. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan, and he continues to hold 216,406 shares directly.

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of common stock at a price of $151.14 per share. The transaction was a direct ownership sale.

After this trade, Rosenbaum continues to hold 217,606 shares of Guidewire common stock directly. According to a footnote, the sale was executed automatically under a pre-arranged Rule 10b5-1 trading plan adopted by the reporting person, indicating it was scheduled in advance rather than timed discretionarily.

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of Common Stock on March 30, 2026 at $145.74 per share. The transaction was an automatic sale made under a Rule 10b5-1 Trading Plan adopted on October 14, 2025.

Following this sale, Rosenbaum directly holds 218,806 shares of Guidewire common stock, indicating the transaction represents a small portion of his overall reported ownership and appears to be a routine, pre-planned disposition.

Guidewire Software’s Chief Executive Officer Michael George Rosenbaum reported an open-market sale of company stock. On March 23, 2026, he sold 1,200 shares of Guidewire Software common stock at a price of $155.56 per share in a transaction classified as an open-market sale.

The sale was executed automatically under a pre-set Rule 10b5-1 trading plan adopted on October 14, 2025, indicating it was scheduled in advance. After this transaction, Rosenbaum still directly owns 220,006 shares of Guidewire Software common stock, so the sale represents only a small fraction of his overall holdings.

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported a sale of 4,737 shares of common stock. The shares were sold at $163.8579 per share, and according to the footnote, the sale was executed by the issuer to cover taxes tied to the settlement of restricted stock units. Following this routine tax-related disposition, he directly holds 221,206 shares of Guidewire common stock.

Guidewire Software, Inc. president John P. Mullen reported an open-market sale of 6,576 shares of common stock on March 17, 2026 at an average price of $163.8579 per share. According to the footnote, these shares were sold by the company to cover taxes tied to restricted stock unit settlement, making this a tax-related, non-discretionary transaction. After this sale, Mullen directly holds 135,407 shares of Guidewire common stock.

Guidewire Software, Inc. Chief Administrative Officer and General Counsel James Winston King reported a small share disposition tied to taxes on equity compensation. He surrendered 1,001 shares of common stock at $163.8579 per share on March 17, 2026, in a transaction described as covering taxes associated with the settlement of restricted stock units. After this event, he directly holds 32,701 shares of Guidewire common stock. Because the shares were used to satisfy tax obligations rather than sold as a discretionary trade, this filing reflects a routine compensation-related adjustment rather than a directional bet on the stock.

Guidewire Software, Inc.’s Chief Financial Officer Jeffrey Elliott Cooper reported a disposition of 1,935 shares of common stock on March 17, 2026 at an average price of $163.8579 per share. According to the footnote, these shares were sold by the issuer to cover taxes tied to the settlement of restricted stock units, making this a tax-related, non-discretionary event rather than a typical open-market sale. After this transaction, Cooper still holds 66,061 shares of Guidewire common stock directly.

Guidewire Software, Inc. Chief Accounting Officer David Franklin Peterson reported a tax-related share disposition. On this Form 4, 273 shares of common stock were sold on March 17, 2026 at an average price of $163.8579 per share.

According to the footnote, the shares were sold by the issuer to cover taxes tied to the settlement of Restricted Stock Units, making this a mechanical tax-withholding event rather than a discretionary open-market sale. After the transaction, Peterson held 12,533 shares of common stock directly.

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of common stock at $160.00 per share. After this transaction, he directly holds 225,943 shares. The sale was executed automatically under a Rule 10b5-1 trading plan adopted on October 14, 2025.

Guidewire Software Chief Financial Officer Jeffrey Elliott Cooper sold 4,757 shares of common stock in an open-market transaction at $158.72 per share. After the sale, he directly holds 67,996 shares. The company notes this trade was not made under a Rule 10b5-1 trading plan and occurred during an open trading window under its insider trading policy.

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum sold 1,200 shares of common stock in an open-market transaction at $166.34 per share on March 9, 2026. The sale was executed automatically under a Rule 10b5-1 trading plan adopted on October 14, 2025.

After this transaction, Rosenbaum directly holds 227,143 shares of Guidewire common stock.

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of common stock on March 2, 2026 at a price of $143.87 per share. Following this transaction, he directly owns 228,343 shares. The sale was executed automatically under a Rule 10b5-1 trading plan adopted on October 14, 2025.

Guidewire Software, Inc. director and Chief Executive Officer Michael George Rosenbaum reported an open-market sale of common stock. He sold 1,200 shares at a price of $125.50 per share in a transaction dated February 23, 2026. After this sale, he continued to hold 229,543 shares of Guidewire common stock directly. The sale was executed automatically under a pre-arranged Rule 10b5-1 trading plan, which had been adopted in advance to systematically sell shares over time.

Guidewire Software, Inc. chief executive Michael George Rosenbaum reported an open-market sale of common stock. On 02/17/2026, he sold 1,200 shares at a price of $127 per share under transaction code S. The filing notes this was an automatic sale under a 10b5-1 trading plan adopted on October 14, 2025. Following the transaction, Rosenbaum directly owned 230,743 shares of Guidewire common stock.

Guidewire Software, Inc. insider trading report: Chief Executive Officer and director Michael George Rosenbaum sold 1,200 shares of Guidewire common stock at $127.77 per share on February 9, 2026. The transaction was an automatic sale under a pre-arranged Rule 10b5-1 trading plan adopted on October 14, 2025.

After this sale, Rosenbaum beneficially owned 231,943 shares of Guidewire common stock in direct ownership form.

Guidewire Software CEO Michael George Rosenbaum reported an automatic sale of common stock under a pre-arranged Rule 10b5-1 trading plan. On 02/02/2026, he sold 1,200 shares of Guidewire common stock at a price of $140.01 per share.

Following this transaction, Rosenbaum beneficially owned 233,143 shares of Guidewire common stock in direct ownership. The filing describes the sale as executed pursuant to a 10b5-1 Trading Plan adopted on October 14, 2025, indicating it was scheduled in advance.

Guidewire Software, Inc. chief executive officer and director Michael George Rosenbaum reported an automatic sale of company stock. On 01/26/2026, he sold 1,200 shares of Guidewire common stock at a price of $160.32 per share in a transaction coded "S" for sale.

The filing notes this was an automatic sale made under a 10b5-1 trading plan adopted by Rosenbaum on October 14, 2025. After this transaction, he directly beneficially owned 234,343 shares of Guidewire common stock.

Guidewire Software, Inc. Chief Executive Officer and director Michael George Rosenbaum reported selling 1,200 shares of common stock on January 20, 2026 at a price of $156.26 per share. The transaction was coded as a sale and was made pursuant to an automatic Rule 10b5-1 trading plan adopted by Rosenbaum on October 14, 2025, meaning it followed a pre-arranged schedule. After this sale, he beneficially owned 235,543 shares of Guidewire common stock held directly.

Guidewire Software's Chief Financial Officer, Jeffrey Elliott Cooper, reported selling 216 shares of common stock on January 13, 2026 at $180.87 per share under an automatic Rule 10b5-1 trading plan he adopted on October 14, 2025.

Following this planned sale, he beneficially owned 72,753 shares of Guidewire common stock in direct ownership.

Guidewire Software CEO Michael George Rosenbaum, who also serves as a director, reported an automatic sale of company common stock. On January 13, 2026, he sold 1,200 shares of Guidewire common stock at a price of $180.87 per share in an open market transaction coded as a sale. The transaction was carried out under a Rule 10b5-1 trading plan that he adopted on October 14, 2025, which means the trades were pre-arranged rather than made at his discretion on the trade date. After this sale, Rosenbaum beneficially owns 236,743 shares of Guidewire common stock directly.

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.

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.

Guidewire Software, Inc. reported that officer James Winston King, Chief Admin Officer and General Counsel, disposed of company common stock in two transactions. On 12/16/2025, 1,457 shares of common stock were sold at an average price of $192.0761 per share, and on 12/18/2025, 1,860 shares were sold at $195 per share.

After these transactions, King beneficially owns 33,702 shares of Guidewire common stock directly. The filing explains that the first transaction reflects shares sold by the issuer to cover taxes associated with the settlement of restricted stock units, and the second transaction was an automatic sale made under a Rule 10b5-1 trading plan adopted on October 15, 2024 and amended on April 14, 2025.

Guidewire Software, Inc. chief financial officer Jeffrey Elliott Cooper reported two sales of the company’s common stock in December 2025. On December 16, 2025, 2,872 shares of common stock were sold at $192.0761 per share, leaving him with 74,201 shares directly owned. On December 18, 2025, a further 1,232 shares were sold at $195 per share, bringing his direct holdings to 72,969 shares.

The disclosure states that the first transaction reflects shares sold by the issuer to cover taxes associated with the settlement of restricted stock units, and that the second transaction was an automatic sale pursuant to a 10b5-1 Trading Plan adopted by the reporting person on October 15, 2024.

Guidewire Software, Inc. Chief Executive Officer and director Michael George Rosenbaum reported a sale of 6,015 shares of common stock on 12/16/2025. The shares were sold at a price of $192.0761 per share, according to the transaction details.

The filing notes that the shares were sold by the issuer to cover taxes associated with the settlement of Restricted Stock Units. After this transaction, Rosenbaum directly beneficially owns 240,743 shares of Guidewire common stock.

Guidewire Software, Inc. reported an insider stock transaction by its chief accounting officer, David Franklin Peterson. On 12/16/2025, 358 shares of Guidewire common stock were sold at $192.0761 per share. The explanation states that the shares were sold by the issuer to cover taxes associated with the settlement of restricted stock units. After this tax-related sale, Peterson beneficially owns 12,806 shares of Guidewire common stock directly.

Guidewire Software president John P. Mullen reported a tax-related transaction in company stock. On 12/16/2025, 7,975 shares of Guidewire common stock were sold at $192.0761 per share.

The explanation states that the issuer sold these shares to cover taxes associated with the settlement of restricted stock units. After this transaction, Mullen directly beneficially owned 141,983 shares of Guidewire common stock.

Guidewire Software director Mark V. Anquillare reported an equity grant from the company. On December 15, 2025, he received 1,196 restricted stock units relating to common stock at a reported price of $0, increasing his directly held amount to 2,716 shares after the transaction. The award is scheduled to become fully vested after the earlier of one year from the grant date or Guidewire Software’s next annual meeting of stockholders.

Guidewire Software, Inc. reported that a director acquired 1,196 restricted stock units of its common stock on December 15, 2025 at a price of $0 per unit.

After this grant, the reporting person beneficially owned 2,371 shares. These restricted stock units are scheduled to become 100% vested after the earlier of one year from the grant date or Guidewire Software’s next annual meeting of stockholders.

Guidewire Software director Rajani Ramanathan received a grant of 1,196 restricted stock units of common stock on December 15, 2025. These units are scheduled to vest 100% after the earlier of one year from the grant date or the company’s next annual meeting of stockholders. Following this grant, she beneficially owns 11,057 shares of Guidewire common stock.

Guidewire Software, Inc. director David S. Bauer received a new equity grant in the form of restricted stock units. On 12/15/2025, he was awarded 1,196 restricted stock units of common stock at a stated price of $0, reported as an acquisition under code "A." Following this grant, he beneficially owned 7,099 shares of common stock, held directly.

The restricted stock units were granted on December 15, 2025 and are scheduled to become 100% vested after the earlier of one year from the grant date or the issuer's next annual meeting of stockholders. This filing reflects equity-based compensation to a board member rather than an open-market purchase or sale.

Guidewire Software, Inc. director Michael C. Keller reported a stock-based compensation grant. On December 15, 2025, he received 1,196 restricted stock units of Guidewire common stock at a stated price of $0, reflecting a typical equity award rather than a cash purchase.

After this grant, Keller beneficially owns 10,606 shares of Guidewire common stock in direct form. The restricted stock units are scheduled to become 100% vested after the earlier of one year from the grant date or the company’s next annual meeting of stockholders, tying his compensation to the company’s long-term performance and governance cycle.

Guidewire Software director Catherine P. Lego reported a new equity award and updated her holdings. On December 15, 2025 she received 1,196 restricted stock units representing common stock, granted at a price of $0. Following this award she beneficially owns 14,393 shares of common stock directly, in addition to 2,000 shares held indirectly through the Catherine Pierson Lego Trust UA DTD 05/09/07, where she is the sole trustee and beneficiary. The restricted stock units are scheduled to vest 100% after the earlier of one year from the grant date or the issuer's next annual meeting of stockholders.

Guidewire Software director Margaret Dillon reported an equity award of the company’s common stock. On December 15, 2025, she acquired 1,196 shares of Guidewire common stock in the form of restricted stock units at a stated price of $0 per share. Following this transaction, she beneficially owns 16,393 shares of Guidewire common stock directly.

According to the footnote, these restricted stock units were granted on December 15, 2025 and are scheduled to become 100% vested after the earlier of one year from the grant date or the issuer’s next annual meeting of stockholders. The report relates to a single reporting person and reflects an acquisition of restricted stock units rather than an open‑market purchase or sale.

Guidewire Software, Inc. chief executive officer and director Michael George Rosenbaum reported selling 1,400 shares of the company’s common stock on 12/15/2025 at a price of $204.34 per share. The transaction was coded as a sale and was carried out automatically under a Rule 10b5-1 trading plan that he adopted on October 15, 2024.

After this transaction, Rosenbaum directly beneficially owns 246,758 shares of Guidewire common stock. This reflects a routine insider share sale by a senior executive and does not describe any change in Guidewire’s operations or financial results.

Guidewire Software, Inc. insider trade disclosed: Guidewire Software's Chief Executive Officer and director Michael George Rosenbaum reported selling 1,400 shares of common stock on 12/08/2025 at a price of $210.87 per share. After this transaction, he beneficially owns 248,158 shares of Guidewire common stock. The sale was executed under an automatic Rule 10b5-1 trading plan that he adopted on October 15, 2024, which pre-schedules trades under set conditions.

Guidewire Software, Inc. insider transaction: A company officer and president reported selling 3,000 shares of Guidewire common stock on 12/01/2025 at a price of $213.44 per share. After this sale, the reporting person beneficially owns 149,958 shares of Guidewire common stock in direct ownership form.

The sale was an automatic transaction made under a pre-arranged Rule 10b5-1 trading plan that the reporting person adopted on October 15, 2024. Such plans are designed to allow insiders to systematically sell shares over time according to preset instructions.

Guidewire Software, Inc. insider trading report: Chief Executive Officer and Director Michael George Rosenbaum reported a sale of common stock of Guidewire Software, Inc. on 12/01/2025. He sold 1,400 shares of common stock at a price of $213.44 per share in a transaction coded "S" for sale. After this transaction, he beneficially owns 249,558 shares of Guidewire common stock in direct ownership form.

The filing notes that this was an automatic sale carried out under a Rule 10b5-1 trading plan adopted by Rosenbaum on October 15, 2024, which is designed to pre-arrange trades according to specified instructions.

Guidewire Software, Inc. (GWRE) reported an insider stock transaction by its Chief Executive Officer and director, Michael George Rosenbaum. On 11/24/2025, he sold 1,400 shares of Guidewire common stock at a price of $213.23 per share.

Following this sale, Rosenbaum beneficially owns 250,958 shares of Guidewire common stock in direct ownership. The filing notes that the sale was an automatic transaction under a Rule 10b5-1 trading plan, which was adopted on October 15, 2024, indicating it was pre-arranged under SEC rules for insider trading plans.

Guidewire Software, Inc. reported an insider share sale by its Chief Executive Officer and Director, Michael George Rosenbaum. On 11/17/2025, he sold 1,400 shares of Guidewire common stock in an open market transaction with a sale code of "S" at a price of $222.54 per share, executed under an automatic Rule 10b5-1 trading plan adopted on October 15, 2024. Following this transaction, he beneficially owns 252,358 shares of Guidewire common stock in direct ownership.

Guidewire Software, Inc. insider trade reported – An officer of Guidewire Software, Inc. (GWRE), serving as Chief Administrative Officer and General Counsel, reported a sale of common stock. On 11/17/2025, the reporting person sold 798 shares of Guidewire common stock at a price of $222.54 per share in a transaction coded "S" for sale. After this transaction, the officer beneficially owned 37,019 shares of Guidewire common stock. The sale was executed under an automatic Rule 10b5-1 trading plan that the reporting person adopted on October 15, 2024 and amended on April 14, 2025.

Guidewire Software (GWRE) CEO and director Michael George Rosenbaum sold 1,400 shares of common stock on 11/10/2025 at a price of $218.53 per share. The transaction was an automatic sale made under a Rule 10b5-1 trading plan adopted on October 15, 2024. Following the sale, he beneficially owns 253,758 shares, held directly.

Guidewire Software (GWRE): CEO and Director Michael George Rosenbaum reported a sale of 1,400 shares of common stock on 11/03/2025 at $231.85 per share. The transaction was an automatic sale under a Rule 10b5-1 trading plan adopted on October 15, 2024. Following the sale, he beneficially owns 255,158 shares, held directly.

Guidewire Software (GWRE) filed a Form 4 disclosing an insider sale. On 11/03/2025, the company’s President sold 3,000 shares of common stock at $231.85 per share under a pre‑set Rule 10b5‑1 trading plan adopted on October 15, 2024. Following the transaction, the reporting person directly beneficially owned 152,958 shares.