King James Winston

Chief Admin Officer/General Counsel Winston sells 7,162 GWRE shares for $1,782,059.40 across 4 transactions on 2025-09-18

King James Winston executed 4 separate sales totaling 7,162 shares for $1,782,059.40 (blended average $248.82), reducing his holdings from 45,777 to 38,615 shares (-15.6%). The sales occurred near recent price strength: the stock trades at $244.60 today, +14.3% over 30 days and +3.0% over 90 days, though currently -6.6% from the 52-week high of $261.88. Examining his same-ticker history at GWRE, his prior 4 measurable sales (2024-09-17 to 2024-09-19) generated positive average 30-day returns (+9.5%) but minimal average 90-day returns (+0.6%), with only 1 of 4 well-timed at the 90-day mark. His cross-ticker track record shows similar patterns: 5 prior sales averaging +9.5% at 30 days and +0.6% at 90 days, with a 25% well-timed rate. The filing provides no FLAGS indicating a scheduled 10b5-1 plan, so this represents discretionary open-market activity. The absence of explanatory context in the FACTS precludes characterization of motive beyond the observable sale event.

King James Winston sold 7,149 GWRE shares at $242.87; holdings reduced to 45,777 shares (45.8K).

King James Winston, Chief Admin Officer and General Counsel, sold 7,149 shares of Guidewire Software at $242.87 on 2025-09-16, reducing his holdings by 13.5% to 45,777 shares. His prior four sales at GWRE generated 90-day returns ranging from -0.4% to +1.5%, with only 1 of 4 being well-timed (negative post-sale price movement). The current sale at $242.87 occurred when the stock was trading 5.7% below its 52-week high of $261.88 and has since risen to $246.94 (+1.7% from transaction price). GWRE's fundamentals remain strong with $293.5M in quarterly revenue, positive $46.0M net income, and 22.6% annual revenue growth, though the elevated P/E of 188.50 warrants investor attention to valuation dynamics. The transaction itself represents a modest portfolio adjustment from a senior executive without material signal of management concern given the company's operational performance.

Chief Admin Officer King James Winston sold 10,312 shares of GWRE for $1,777,571.32 across 4 transactions (Sept 17–19), retaining 48,237 shares post-sale.

King James Winston, Chief Admin Officer and General Counsel, executed 4 separate sales totaling 10,312 shares for $1,777,571.32 between September 17–19, 2024, at prices ranging from $171.94 to $173.88. The sales reduced his holdings by 17.6%, from 58,549 shares to 48,237 shares. The stock currently trades at $174.65, within 0.0% of its 52-week high of $174.65, and has appreciated 18.9% over the past 30 days and 27.2% over 90 days. These sales occurred against a backdrop of strong recent price momentum and a company that reported a net loss of $-5,478,000.00 in its latest quarter, despite 8.3% annual revenue growth and a $14.5B market capitalization.