Guidewire CEO Sells $181K in Shares

Michael George Rosenbaum sells 1,200 shares of Guidewire Software stock

Apr. 7, 2026 at 8:36am

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A sleek, metallic paperweight or trophy floating against a plain white background, symbolizing the financial performance and leadership of Guidewire Software.Guidewire CEO's recent stock sale reflects potential uncertainty about the company's future growth.San Mateo Today

Guidewire Software CEO Michael George Rosenbaum sold 1,200 shares of the company's stock on Monday, April 6th, for a total transaction of $181,368. This represents a 0.55% decrease in his ownership of the stock, which he now holds 217,606 shares valued at $32.9 million.

Why it matters

Insider trading activity can provide insights into a company's performance and management's confidence in the business. While this sale represents a small portion of Rosenbaum's overall stake, it may signal that he believes the stock is overvalued at current levels.

The details

Rosenbaum's sale was executed under a pre-arranged Rule 10b5-1 trading plan, which allows company insiders to schedule stock transactions in advance and avoid allegations of insider trading. This was one of several recent stock sales by Rosenbaum, who has sold 1,200 shares on a near-monthly basis since January 2026.

  • On April 6, 2026, Rosenbaum sold 1,200 shares at an average price of $151.14.
  • On March 23, 2026, Rosenbaum sold 1,200 shares at an average price of $155.56.
  • On March 17, 2026, Rosenbaum sold 4,737 shares at an average price of $163.86.

The players

Michael George Rosenbaum

CEO of Guidewire Software, Inc.

Guidewire Software, Inc.

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

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What they’re saying

“This represents a 0.55% decrease in their ownership of the stock.”

— Michael George Rosenbaum, CEO

The takeaway

Rosenbaum's regular stock sales, while not unusual for a CEO, may raise questions about his long-term confidence in Guidewire's growth prospects. Investors will likely be watching to see if this trend continues or if Rosenbaum increases his stake in the company in the future.