Insider Trading February 17, 2026

Guidewire CEO Executes $152,400 Share Sale as Stock Trades Near 52-Week Low

Automatic 10b5-1 sale by Michael George Rosenbaum coincides with a fresh $500 million buyback authorization and analyst rating moves

By Avery Klein GWRE
Guidewire CEO Executes $152,400 Share Sale as Stock Trades Near 52-Week Low
GWRE

Guidewire Software Chief Executive Officer Michael George Rosenbaum sold 1,200 shares on February 17, 2026, netting $152,400 in an automated transaction under a 10b5-1 plan. The sale occurred while the stock traded close to its 52-week low, even as the company announced a new $500 million repurchase program and received analyst upgrades following fiscal Q1 2026 results.

Key Points

  • CEO Michael George Rosenbaum sold 1,200 shares on February 17, 2026 at $127.00 per share, totaling $152,400; the sale was executed under a 10b5-1 plan adopted October 14, 2025.
  • After the transaction Rosenbaum directly owns 230,743 shares of Guidewire Software; the stock has traded near a 52-week low of $120.37 and declined over 42% in the past six months.
  • Guidewire announced a new $500 million share repurchase program after exhausting the remaining $138.2 million from its previous authorization; DA Davidson upgraded the stock to Buy (PT $246) and Citizens reiterated Market Outperform (PT $300) following fiscal Q1 2026 results.

Guidewire Software (NASDAQ: GWRE) reported an automatic sale by its chief executive on February 17, 2026, when Michael George Rosenbaum disposed of 1,200 shares of the company's common stock at $127.00 per share, a transaction totaling $152,400.

The sale was executed under a pre-arranged 10b5-1 trading plan that Rosenbaum adopted on October 14, 2025. Following the disposition, Rosenbaum continues to hold 230,743 shares of Guidewire.

The transaction took place as Guidewire's share price traded near a 52-week low of $120.37, and the stock had declined by more than 42% over the prior six months, according to InvestingPro data.


Company financials and liquidity

InvestingPro data cited in company reports indicates that Guidewire remains profitable, with positive net income and expectations for growth in net income this year. The company’s balance sheet shows a current ratio of 3.48, suggesting that liquid assets comfortably exceed short-term obligations.

InvestingPro also highlights that Guidewire is included among its covered US equities with an in-depth Pro Research Report available to subscribers.


Share repurchase program and analyst activity

In a separate corporate action, Guidewire’s board approved a new $500 million share repurchase program, effective immediately. The new authorization follows the completion of the company’s prior buyback plan, under which the remaining $138.2 million had been exhausted.

Analyst coverage shifted in the wake of Guidewire’s fiscal first-quarter 2026 results. DA Davidson upgraded the stock from Neutral to Buy while keeping a $246 price target. Citizens reiterated a Market Outperform rating and maintained a $300 price target. The board authorized the new buyback to allow repurchases of common stock through various means.

The buyback announcement was accompanied by relative stability in the stock’s trading performance.


Context and takeaway

The disclosed sale by Rosenbaum was carried out automatically within the parameters of his 10b5-1 trading plan and left him with an established ownership stake. At the same time, Guidewire’s liquidity metrics and continued profitability, together with a sizable new repurchase program and recent analyst rating changes, provide multiple data points for market participants evaluating the company. The stock’s recent decline and proximity to its 52-week low remain relevant factors for investors monitoring the name.

Risks

  • The company's share price has fallen more than 42% over six months and is trading close to its 52-week low of $120.37 - a continued share price decline remains a near-term market risk.
  • Investor interpretation of an insider sale can vary; although Rosenbaum’s transaction was automatic under a 10b5-1 plan, some market participants may view insider sales negatively in volatile market environments.
  • Despite the new $500 million buyback authorization, the announcement so far has coincided with stable trading rather than immediate upward price movement, leaving uncertainty about the program’s near-term impact on market valuation.

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