Guidewire CEO may sell $10.4M in company stock
Guidewire’s CEO filed a Rule 144 notice to potentially sell up to 72,290 shares, primarily to cover tax withholding on equity awards vesting in September 2026.
Rhea-AI Filing Summary
Guidewire Software, Inc. (GWRE) received a Rule 144 notice indicating that Chief Executive Officer Michael George Rosenbaum may sell up to 72,290 shares of common stock through Morgan Stanley Smith Barney. The notice references an aggregate market value of approximately $10,443,866.46 for these shares, with 81,992,669 shares outstanding as of September 17, 2026. The shares to be sold relate to RSU and PSU awards vesting on September 15, 2026, which were originally granted between 2022 and 2025. The filer states these are automatic sell-to-cover transactions to satisfy tax withholding obligations under Guidewire’s Amended and Restated 2020 Stock Plan.
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Key Figures
Shares to be sold under Rule 144: 72,290 shares
Aggregate market value of shares to be sold: $10,443,866.46
Shares outstanding: 81,992,669 shares
+4 more
7 metrics
Shares to be sold under Rule 144
72,290 shares
Maximum number of Guidewire common shares covered by the notice
Aggregate market value of shares to be sold
$10,443,866.46
Value associated with the 72,290 shares in the Rule 144 notice
Shares outstanding
81,992,669 shares
Guidewire common shares outstanding as of September 17, 2026
RSU vesting tranche
3,723 shares
RSUs vesting September 15, 2026 from a grant dated September 15, 2022
PSU vesting tranche
123,074 shares
PSUs vesting September 15, 2026 from a grant dated September 13, 2023
Example prior sale amount
$175,044
Proceeds reported for a 1,200-share sale of common stock on September 14, 2026
Example prior sale share count
1,200 shares
Size of each disclosed common stock sale in the past three months section
Key Terms
Rule 144, sell-to-cover, RSU, PSU, +1 more
5 terms
Rule 144 regulatory
"See the definition of "person" in paragraph (a) of Rule 144"
Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.
sell-to-cover financial
"reflect automatic sell-to-cover transactions to satisfy tax withholding obligations"
Sell-to-cover is when part of newly issued or exercised company stock is immediately sold to pay required taxes and fees, so the recipient keeps the remaining shares. For investors this matters because it reduces the number of shares insiders or employees actually hold after a grant, can create small, routine share sales that aren’t signal of cashing out, and slightly increases share supply on the market—like selling a portion of a paycheck to cover the tax bill.
RSU financial
"Vesting of RSU (Grant Date: 09/15/2022)"
Restricted stock units (RSUs) are a form of company shares given to employees as part of their compensation, usually with certain restrictions or conditions, such as remaining with the company for a set period. When these restrictions lift, employees receive actual shares that they can sell or hold. For investors, RSUs can impact a company's stock supply and reflect the company's commitment to attracting and retaining talent.
PSU financial
"Vesting of PSU (Grant Date: 09/13/2023)"
A PSU is a company where the government owns a controlling stake and often plays a direct role in its management and strategy. Think of it like a business that operates with public oversight, similar to a town-run utility versus a private neighborhood service. Investors watch PSUs differently because government involvement can affect profits, dividend policies, regulatory treatment and stability, so these stocks may behave more like policy instruments than pure market-driven enterprises.
Amended and Restated 2020 Stock Plan financial
"under the Issuer's Amended and Restated 2020 Stock Plan"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What does the GWRE Rule 144 filing disclose about planned stock sales?
The notice states that CEO Michael George Rosenbaum may sell up to 72,290 shares of Guidewire common stock under Rule 144, with an indicated aggregate market value of about $10,443,866.46, based on data as of September 17, 2026.
What equity awards are vesting for the GWRE CEO in connection with this Rule 144 filing?
The filing lists vesting on September 15, 2026 of several awards, including 3,723 RSU shares granted September 15, 2022 and 123,074 PSU shares granted September 13, 2023, plus additional RSU tranches from 2023, 2024, and 2025.
What prior Guidewire (GWRE) stock sales by the CEO are disclosed in the last three months?
The notice lists multiple sales of 1,200 shares of common stock each on various dates, including June 22, 2026, July 6, 2026, and September 14, 2026, with total dollar amounts shown for each sale such as $149,148 and $175,044.
Which broker is named in the Guidewire (GWRE) Rule 144 filing?
The filing identifies Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza in New York, as the broker associated with the planned sale of 72,290 shares of Guidewire common stock.
AI-generated analysis. How Rhea-AI works. Not financial advice.
