Guidewire CEO Michael Rosenbaum Sells Shares for $187,104
Key Points
The transaction involved 1,200 shares at $155.92 per share, totaling $187,104 on August 3, 2026.
This disposition reduced the executive's direct equity holdings by 0.62%.
The activity was executed under a Rule 10b5-1 trading plan adopted on October 14, 2025.
Michael George Rosenbaum maintains a direct position of 191,376 shares valued at ~$30 million as of the August 3, 2026 market close.
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Chief Executive Officer Michael George Rosenbaum sold 1,200 shares of Guidewire Software, Inc. (NYSE:GWRE) on Aug. 3, 2026. SEC Form 4 filing
Transaction summary
| Metric | Value |
|---|---|
| Transaction value | $187,104 |
| Shares sold | 1,200 |
| Post-transaction shares (directly held) | ~191,000 |
| Post-transaction value | ~$30.1 million |
Transaction value based on SEC Form 4 weighted average sale price ($155.92); post-transaction value based on Aug. 3, 2026, market close ($157.33).
Key questions
- How does this sale align with the executive's total equity exposure?
The transaction represents a marginal adjustment to the CEO's holdings, involving less than 1% of his total direct position in the software company. - What is the context of the Rule 10b5-1 trading plan?
The sale was pre-scheduled under a plan established in October 2025, providing a structured liquidity mechanism that operates independently of current market conditions or corporate developments. - How has the stock performed leading up to this transaction?
As of the Aug. 3, 2026, transaction date, the company's shares had realized a -29% return over the preceding 12 months. - What remains of the executive's direct equity stake?
Following this transaction, Michael George Rosenbaum continues to hold 191,376 shares directly, representing a 0.23% ownership interest in the firm.
Company Overview
| Metric | Value |
|---|---|
| Share Price (as of market close 2026-08-03) | $157.33 |
| Market Capitalization | $13.1 billion |
| Revenue (TTM) | $1.4 billion |
| Net Income (TTM) | $159.8 million |
Company Snapshot
- Guidewire Software provides comprehensive software solutions for the property and casualty insurance industry, with primary offerings including Guidewire InsuranceSuite (featuring PolicyCenter, BillingCenter, and ClaimCenter applications) and Guidewire InsuranceNow, a cloud-native platform for integrated policy, billing, and claims administration.
- The company generates revenue through a combination of subscription-based cloud services, software licensing, and professional services, enabling insurers to modernize their core operations and reduce time-to-market for new insurance products.
- Guidewire serves property and casualty insurance carriers of all sizes globally, including regional and national insurers seeking to transform their digital capabilities and operational efficiency.
Guidewire Software is a market-leading provider of digital transformation solutions for the insurance industry, with a market capitalization of $13.1 billion and trailing-12-month revenue of $1.4 billion.
The company maintains a competitive advantage through its specialized domain expertise in insurance operations, a comprehensive, integrated platform architecture, and established customer relationships across a substantial portion of the global insurance market.
Guidewire's strategic positioning in the high-growth software-as-a-service segment reflects the insurance industry's ongoing digital transformation and operational modernization initiatives.
What this transaction means for investors
This sale shouldn’t be concerning for investors. Insiders typically use Rule 10b5-1 for pre-planned transactions to avoid the appearance of acting on any material non-public information. The sale represents a tiny percentage of his overall stake in the company’s stock.
Guidewire stock has fallen over the past year. However, this decline contrasts with strong momentum in the business. On a trailing-12-month basis, revenue grew 25% year over year to $1.4 billion, while operating profit surged to $117 million.
Importantly, management credits the momentum in part to the successful integration of AI offerings. This suggests there could be more growth ahead, given that AI adoption is still in its early stages.
Overall, the stock’s pullback looks more like a buying opportunity. The shares are trading at a lower forward price-to-earnings multiple of 45, even as analysts expect 56% annualized earnings growth in the next two years.
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John Ballard has no position in any of the stocks mentioned. The Motley Fool has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy.
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