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Top Guidewire Executives Quietly Unload a Significant Chunk of Shares

Top Guidewire Executives Quietly Unload a Significant Chunk of Shares

New insider activity at Guidewire ( (GWRE) ) has taken place on December 18, 2025.

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Guidewire has seen notable insider activity, with two top executives recently selling company stock. Chief Administrative Officer and General Counsel James Winston King sold 1,457 shares of Guidewire, generating proceeds of $279,845. Meanwhile, Chief Financial Officer Jeffrey Elliott Cooper sold 2,872 shares, for a total sale value of $551,625. These transactions highlight significant share disposals by key members of the company’s leadership team.

Recent Updates on GWRE stock

Over the last 24 hours, Guidewire has drawn positive analyst commentary despite its shares having pulled back about 20% since its strong Q1 earnings in early December. DA Davidson upgraded the stock after this decline, viewing the selloff as an opportunity because the company is making solid progress transitioning to a cloud/subscription model, which is expected to drive mid‑teens annual revenue growth and faster growth in recurring subscription revenue, reinforcing its leadership in InsureTech. BTIG assumed and initiated coverage with a favorable stance, citing Guidewire as a leading platform for modernizing the property and casualty insurance market with a large addressable opportunity and arguing that recent share weakness contrasts with a “blowout” Q1. That quarter showed robust ARR and revenue growth, rapid expansion in subscription and support revenue, accelerating cloud adoption with multiple new cloud deals, and the launch of new products (PricingCenter and UnderwritingCenter) plus the ProNavigator AI acquisition, all underpinning a raised full‑year outlook. While management flagged near‑term pressure on cash flow and service margins due to bonuses, commissions, and ongoing investments in capacity and AI, analysts appear to view these as strategic, long‑term growth drivers rather than fundamental setbacks.

Spark’s Take on GWRE Stock

According to Spark, TipRanks’ AI Analyst, GWRE is a Neutral.

Guidewire’s overall stock score is driven by strong earnings call performance and solid financials, despite technical and valuation challenges. The company’s strategic focus on cloud transformation and positive financial outlook are significant strengths. However, high valuation and mixed technical signals present risks.

To see Spark’s full report on GWRE stock, click here.

More about Guidewire

YTD Price Performance: 14.41%

Average Trading Volume: 822,554

Technical Sentiment Signal: Buy

Current Market Cap: $16.46B

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