Robinson Andrew S

Chairman & CEO Robinson buys 22,100 shares ($1.0M) at blended $46.76; 2 other insiders also bought within 14 days.

Robinson Andrew S, the Chairman & CEO, executed 2 separate open-market purchases totaling 22,100 shares for $1,033,370.23 on 2026-02-27, increasing his holdings by 15.2% to 167,674 shares. The stock is currently trading at $46.47, down 28.5% from its 52-week high of $65.00, though up 3.3% over the past 30 days. Critically, a cluster pattern has emerged: 2 other insiders also purchased within the past 14 days, suggesting coordinated interest at current valuation levels. The company shows solid fundamentals with annual revenue growth of +29.8%, net income of $45,901,000.00, and a P/E of 13.32, though the stock's extended decline from peak warrants observation of whether this cluster activity represents institutional appetite or reflects divergent signals relative to recent price momentum.

CEO Robinson sold 36,271 shares at $62.65 on 2025-06-06 for $2,272,374.77; post-transaction holdings 65,269 shares.

Robinson Andrew S, Chairman & CEO of Skyward Specialty Insurance Group, Inc. (SKWD), executed 2 separate sales totaling 36,271 shares for $2,272,374.77 on 2025-06-06, reducing his holdings from 101,540 to 65,269 shares (a -35.7% reduction). At the time of sale the blended average price was $62.65, which was near the 52-week high of $65.00. Evaluated against his same-ticker history, this sale reflects a pattern observed in 4 prior SKWD sales: his prior sells have not been well-timed at the 90-day mark (0 of 4 measurable outcomes showed negative 90d returns), suggesting the insider has historically sold ahead of continued appreciation. The stock is now trading at $58.19, down 10.5% from the 52-week high and down 2.8% over 30 days, placing this recent sale in territory where the stock has declined since execution. The company's fundamentals remain solid with annual revenue growth of +29.8%, net income of $42,058,000.00, and a P/E of 18.95, indicating the sale occurred from strength rather than distress.

CEO Andrew S Robinson sold 13,786 shares of SKWD at $59.23 on 2025-05-08; stock at 52-week high, post-sale holdings: 101,540 shares

Robinson Andrew S sold 13,786 shares, reducing his holdings from 115,326 to 101,540 shares, a 12.0% reduction in position size. The sale occurred at $59.23, with the stock currently trading at $59.87 at its 52-week high, indicating the sale took place near peak valuation. At the same-ticker level, his 4 prior measurable sells at SKWD all posted positive returns within 90 days (ranging +5.4% to +8.1%), suggesting his prior exit decisions at this ticker occurred before subsequent appreciation—a pattern inconsistent with selling ahead of declines. The fundamentals remain solid with revenue growth of +29.8% annually and a P/E of 19.50, providing no obvious distress signal for the transaction.

SKWD CEO Andrew S Robinson sold 20,311 shares at $50.24; holdings decline 19.8% to 82,044 shares

Robinson, CEO of Skyward Specialty Insurance Group, executed a $1,020,422.61 sale of 20,311 shares at $50.24 on March 6, 2025, reducing his holdings by 19.8% from 102,355 to 82,044 shares. The stock currently trades at $47.26, down 14.0% from its 52-week high of $54.93; Robinson sold near the upper end of recent trading range. His same-ticker trading history at SKWD shows five prior sales in January 2025 with strong 30-day reversals (ranging from +6.6% to +9.5%), though no measurable 90-day outcomes yet—in contrast, his cross-ticker track record across 19 prior open-market sales shows a 0.00% well-timed rate at the 90-day mark and average +3.3% returns after his sells, indicating those transactions generally preceded rallies rather than declines. The company reports solid fundamentals: $300.9M quarterly revenue, +29.8% annual revenue growth, P/E of 11.39, and $36.7M net income. This sale stands out as a material reduction of the CEO's ownership stake during a period of strong operational performance, warranting closer examination of the discretionary versus scheduled nature of the transaction.

CEO Andrew S Robinson sells 11,274 shares at $45.30 avg ($510.7K) on SKWD, reducing stake 17.7%; stock now -22.6% from 52-week high.

Robinson Andrew S, CHAIRMAN & CEO of Skyward Specialty Insurance Group, Inc., executed 5 separate sales totaling 11,274 shares for $510,693.60 across January 7-8, 2025, at a blended average price of $45.30, reducing his holdings from 63,629 shares to 52,355 shares. The timing is notable: these sales occurred as the stock has declined 22.6% from its 52-week high of $54.93 and 16.9% over the past 30 days, with the current price at $42.51. The company's fundamentals remain relatively stable with a P/E of 12.77, annual revenue growth of +37.9%, and a market cap of $1.7B, suggesting the CEO is selling into a deteriorated price environment rather than from a position of strength. Additionally, this represents the fifth distinct sale at SKWD within a week (prior sells on 2025-01-02, 2025-01-03, and 2025-01-06), establishing a pattern of consistent share liquidation; however, outcomes from these recent prior trades are not yet measurable given their proximity to the current filing date.

CEO Robinson sells 19,525 shares for $942,231.35 across five transactions Jan 2–6; stock now down -16.0% in 30 days from sale prices.

Robinson Andrew S, Chairman & CEO of Skyward Specialty Insurance Group, executed 5 separate sales totaling 19,525 shares for $942,231.35 between January 2–6, 2025, at blended average price of $48.26. The stock has since declined to a current price of $45.09, trading -17.9% from its 52-week high of $54.93 and down -16.0% in the 30-day period following the sales. His prior 5 trades at SKWD all posted positive 90-day returns (ranging +1.0% to +7.9%), meaning none resulted in downside captures at that horizon—a 0% well-timed rate at this ticker. The sales reduced his holdings by 23.5%, from 83,154 to 63,629 shares, leaving him with a substantial remaining position. Company fundamentals remain solid: FY revenue growth of +37.9%, P/E of 13.54, and net income of $36,668,000 on quarterly revenue of $300,888,000.