Skyward Specialty Insurance Group (NASDAQ:SKWD) CEO Buys $1,033,396.00 in Stock

Skyward Specialty Insurance Group, Inc. (NASDAQ:SKWD) CEO Andrew Robinson acquired 22,100 shares of the business’s stock in a transaction on Friday, February 27th. The shares were purchased at an average cost of $46.76 per share, for a total transaction of $1,033,396.00. Following the completion of the transaction, the chief executive officer owned 167,674 shares in the company, valued at approximately $7,840,436.24. This represents a 15.18% increase in their position. The acquisition was disclosed in a filing with the Securities & Exchange Commission, which is available at this link.

Skyward Specialty Insurance Group Stock Performance

Shares of NASDAQ:SKWD opened at $46.47 on Monday. The firm has a market capitalization of $1.88 billion, a P/E ratio of 11.42 and a beta of 0.54. The stock has a 50 day moving average price of $46.80 and a 200-day moving average price of $47.46. Skyward Specialty Insurance Group, Inc. has a 52-week low of $42.45 and a 52-week high of $65.05.

Skyward Specialty Insurance Group (NASDAQ:SKWD) last issued its quarterly earnings results on Monday, February 23rd. The company reported $1.17 earnings per share for the quarter, topping the consensus estimate of $0.96 by $0.21. The company had revenue of $385.59 million for the quarter, compared to analysts’ expectations of $380.86 million. Skyward Specialty Insurance Group had a return on equity of 18.51% and a net margin of 12.00%.During the same period in the prior year, the firm earned $0.80 earnings per share. On average, equities analysts forecast that Skyward Specialty Insurance Group, Inc. will post 3.05 EPS for the current fiscal year.

Analysts Set New Price Targets

Several equities research analysts recently commented on SKWD shares. Weiss Ratings raised shares of Skyward Specialty Insurance Group from a “hold (c+)” rating to a “buy (b-)” rating in a research note on Friday. Piper Sandler dropped their price target on Skyward Specialty Insurance Group from $65.00 to $55.00 and set an “overweight” rating on the stock in a research report on Thursday. Raymond James Financial set a $66.00 price target on Skyward Specialty Insurance Group in a research note on Friday, December 5th. Citizens Jmp set a $80.00 price objective on Skyward Specialty Insurance Group in a research report on Thursday, December 4th. Finally, Susquehanna set a $80.00 target price on Skyward Specialty Insurance Group in a report on Friday, January 16th. One equities research analyst has rated the stock with a Strong Buy rating, eight have given a Buy rating and three have issued a Hold rating to the stock. According to MarketBeat, Skyward Specialty Insurance Group presently has a consensus rating of “Moderate Buy” and an average target price of $65.80.

Skyward Specialty Insurance Group News Roundup

Here are the key news stories impacting Skyward Specialty Insurance Group this week:

• Positive Sentiment: CEO Andrew S. Robinson purchased 22,100 shares (~$1.03M) on Feb 27, raising his stake by ~15%. Large insider buys are typically viewed as a strong signal of management confidence and can attract buyers. SEC Filing
• Positive Sentiment: Zacks upgraded SKWD to a Rank #2 (Buy), citing improving earnings prospects. Upgrades from a well-known research provider can drive near‑term buying interest. Zacks Article
• Positive Sentiment: Keefe, Bruyette & Woods raised its price target from $69 to $70 and maintained an “outperform” rating — a bullish, high-upside signal (≈50% above current levels) that can attract momentum traders. Benzinga TickerReport
• Positive Sentiment: Aggregator American Banking News shows analysts’ consensus as roughly a “Moderate Buy,” reinforcing the market’s constructive stance. Consensus language supports continued investor interest. American Banking News
• Neutral Sentiment: Summary of the company’s Q4 2025 earnings call is available; recall SKWD reported a beat on EPS and revenue on Feb 23, which underpins the positive analyst activity but doesn’t add new catalyst today. Earnings Call Summary
• Negative Sentiment: Piper Sandler trimmed its price target from $65 to $55 while keeping an “overweight” rating. A lower PT from a mid‑tier sell‑side name may create some short‑term selling or reduce upside expectations. Benzinga

Institutional Investors Weigh In On Skyward Specialty Insurance Group

Institutional investors have recently modified their holdings of the business. Y Intercept Hong Kong Ltd grew its stake in shares of Skyward Specialty Insurance Group by 407.4% in the third quarter. Y Intercept Hong Kong Ltd now owns 54,384 shares of the company’s stock worth $2,587,000 after acquiring an additional 43,666 shares during the period. Squarepoint Ops LLC boosted its holdings in Skyward Specialty Insurance Group by 116.6% in the second quarter. Squarepoint Ops LLC now owns 89,436 shares of the company’s stock worth $5,169,000 after purchasing an additional 48,148 shares during the last quarter. Federated Hermes Inc. boosted its holdings in Skyward Specialty Insurance Group by 5.5% in the second quarter. Federated Hermes Inc. now owns 490,526 shares of the company’s stock worth $28,347,000 after purchasing an additional 25,711 shares during the last quarter. Reinhart Partners LLC. grew its position in Skyward Specialty Insurance Group by 68.2% in the 3rd quarter. Reinhart Partners LLC. now owns 1,613,536 shares of the company’s stock worth $76,740,000 after purchasing an additional 654,500 shares during the period. Finally, American Century Companies Inc. raised its stake in Skyward Specialty Insurance Group by 6.0% during the 2nd quarter. American Century Companies Inc. now owns 598,762 shares of the company’s stock valued at $34,602,000 after buying an additional 34,129 shares during the last quarter. 94.83% of the stock is owned by hedge funds and other institutional investors.

About Skyward Specialty Insurance Group

Skyward Specialty Insurance Group, Inc (NASDAQ: SKWD) is a publicly traded specialty property and casualty insurance underwriter. The company focuses on niche market segments, offering tailored insurance solutions designed to address the specific risk profiles of its target industries.

Through its underwriting platform, Skyward Specialty provides coverage in areas including general liability, professional liability, commercial package, inland marine and other selected specialty lines. Its products are distributed primarily through a network of wholesale brokers, program administrators and managing general agents, enabling the company to reach a diverse client base and adapt quickly to evolving market needs.

Headquartered in the United States, Skyward Specialty Insurance Group operates across multiple states and applies data-driven underwriting and risk management practices to maintain disciplined reserving and consistent performance.