SKWD Skyward Specialty Insurance Group, Inc. Insider Trading

Director Anthony J Kuczinski buys 2,000 SKWD shares ($94.2K) at $47.10 blended avg; stock down 27.8% from 52-week high.

Director Anthony J Kuczinski executed 3 separate purchases totaling 2,000 shares for $94,200.00 on 2026-05-21, increasing his holdings by 14.3%. The purchases occurred at prices near the current market level ($47.00), at a time when SKWD trades 27.8% below its 52-week high of $65.05. His prior trades at SKWD show mixed timing outcomes: 2 of 4 measurable prior buys posted positive 90-day returns, but the most recent two purchases (2026-03-03 and 2026-03-02) both posted negative 30-day and 90-day returns. The company exhibits strong fundamentals with 23.2% annual revenue growth, a 10.73 P/E, and $49.7M net income on $475.9M quarterly revenue. This transaction represents continued accumulation by a director during a period of significant stock weakness from recent highs.

Director Kuczinski bought 5,000 SKWD shares totaling $239,464.50 over 3 days; cluster buy pattern with 3 other insiders in past 14 days.

Anthony J Kuczinski executed 3 separate purchases totaling 5,000 shares for $239,464.50 between 2026-02-27 and 2026-03-03 at prices ranging from $46.88 to $48.79, increasing his holdings by 72.4% from 6,903 to 11,903 shares. The current price of $48.65 is near the blended average purchase price of $47.89, and this filing coincides with a cluster pattern of 3 other insiders buying within the past 14 days—a notable synchronized purchasing signal. Skyward's fundamentals show strong performance with annual revenue growth of +23.2%, net income of $45.9M, and a modest P/E of 11.24, suggesting the company trades at a reasonable valuation relative to earnings. The stock is currently -25.2% from its 52-week high of $65.00, having gained +8.6% over the prior 30 days, positioning this purchase window during a period of recent positive momentum after a significant drawdown.

Director Peirce Christopher Locke bought 3,200 shares of SKWD at $47.30; 3 other insiders also bought within 14 days amid cluster pattern.

Director Peirce Christopher Locke purchased 3,200 shares at $47.30 on 2026-03-02, establishing an initial position in Skyward Specialty Insurance Group after holding zero shares prior to this transaction. This buy occurs within a 14-day window where 3 other insiders also purchased stock, forming a cluster buy pattern that suggests alignment among multiple company officials. The company trades at a P/E of 11.14 with recent quarterly revenue of $382.5M and net income of $45.9M, supporting solid fundamental footing. The stock is currently trading at $48.22, down 25.8% from its 52-week high of $65.00, though it has recovered 8.1% over the past 30 days and 6.7% over 90 days—providing context for the entry point relative to recent volatility.

CFO McHarg buys 200 SKWD shares at blended $46.60; cluster buy pattern with 3 other insiders in past 14 days

McHarg Taryn Leonie, CFO, executed 2 separate purchases totaling 200 shares for $9,320.00 at an average of $46.60 on 2026-02-27, moving from a short position of -100 shares to a net long position of 100 shares. This purchase occurs within a cluster: 3 other insiders also bought within the past 14 days, suggesting coordinated directional interest at the current price level. The stock is trading at $48.22, approximately 30-day change +8.1%, and sits 25.8% below its 52-week high of $65.00, creating a context of recent gains but substantial distance from peak. The company's fundamentals show solid metrics (P/E 11.14, annual revenue growth +23.2%, quarterly revenue $382.5M with net income $45.9M), though the multi-insider buying pattern deserves monitoring to determine whether it reflects internal confidence or other considerations.

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.

SKWD CFO Mark Haushill sold 63,314 shares for $3,723,692.57 in two separate transactions at blended average price $58.81.

Mark Haushill, EVP & CFO of Skyward Specialty Insurance Group, Inc., completed 2 separate sales on 2025-06-13 and 2025-06-16, selling 52,748 shares at $58.76 and 10,566 shares at $59.07 respectively, reducing his holdings by 34.0% from 186,377 to 123,063 shares. The sales occurred near the stock's 52-week high of $65.00 (current price $58.57 is -9.9% from that peak), and within a 90-day window the stock has gained 18.5%, suggesting the insider sold before recent strength rather than during it. His prior 4 sales at this ticker have produced mixed results: 1 was well-timed (stock fell after), while 3 resulted in subsequent gains of +1.8%, +1.6%, and +2.2% at the 90-day mark, indicating his historical timing at SKWD has not been consistently predictive of near-term declines.

SKWD Chair & CEO Robinson sells 36,271 shares for $2.3M via pre-arranged 10b5-1 plan

Robinson Andrew S, CHAIRMAN & CEO of Skyward Specialty Insurance Group (SKWD), executed two separate sales totaling 36,271 shares for $2,272,374.77 on 2025-06-06. The sales occurred at blended average price of $62.65, reducing his holdings from 101,540 shares to 65,269 shares post-transaction. Critically, this transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2024-09-10, meaning it was scheduled and not a discretionary trade decision. As a scheduled disposition under a Rule 10b5-1 plan, this activity reflects compliance mechanics rather than real-time market or conviction signals.

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.

Robinson (CEO) executes 5 sales totaling 11,274 shares for $510,693.60 under 10b5-1 plan adopted Aug 2024

Robinson Andrew S, Chairman & CEO of Skyward Specialty Insurance Group, executed 5 separate sales totaling 11,274 shares for $510,693.60 on January 7–8, 2025, at a blended average price of $45.30 per share. This represents a reduction of 17.7% from his pre-transaction holdings of 63,629 shares, leaving him with 52,355 shares post-transaction. The transaction is governed by a pre-arranged 10b5-1 trading plan adopted on 2024-08-08, meaning the sales were scheduled and programmatic rather than discretionary responses to market conditions. Since the plan was established months in advance, these sales do not reflect real-time decision-making by the CEO but rather an automated execution schedule agreed upon earlier.