Guidewire Software CEO Sells $181K in Stock

Insider transaction follows recent stock repurchase authorization.

Apr. 9, 2026 at 8:38am

A minimalist studio photograph featuring a stack of polished metal coins or tokens floating on a clean, monochromatic background, conceptually representing corporate finance and stock market activity.Insider trading activity can provide clues about a company's financial health and market outlook.San Mateo Today

Guidewire Software CEO Michael George Rosenbaum sold 1,200 shares of the company's stock on April 6th, 2026 for a total transaction of $181,368. The sale represented a 0.55% decrease in Rosenbaum's ownership stake in the technology company, which provides software products and cloud services for property and casualty insurance carriers.

Why it matters

Insider selling can sometimes signal a lack of confidence in a company's future prospects, though Rosenbaum's sale was executed under a pre-arranged trading plan. The transaction follows Guidewire's recent $500 million share repurchase authorization, which suggests the board believes the stock is undervalued.

The details

Rosenbaum's sale was executed at an average price of $151.14 per share. After the transaction, he still directly owns 217,606 shares in Guidewire, valued at approximately $32.9 million. The company's stock has traded in a 52-week range of $120.37 to $272.60.

  • The stock sale occurred on Monday, April 6, 2026.
  • Guidewire announced a $500 million share repurchase plan on January 8, 2026.

The players

Michael George Rosenbaum

CEO of Guidewire Software, Inc.

Guidewire Software, Inc.

A software company that provides products and cloud services for property and casualty insurance carriers.

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The takeaway

Rosenbaum's insider sale, while not unexpected given the pre-arranged nature, comes amid Guidewire's recent share repurchase authorization. This suggests the company's board sees the stock as undervalued, even as the CEO trims his personal stake.