Form 4: Skyward Specialty Insurance CFO Sells Over 63,000 Shares Under Pre-Arranged Trading Plan

Mark W. Haushill, Executive Vice President and Chief Financial Officer of Skyward Specialty Insurance Group, Inc., sold a total of 63,314 shares of common stock in two transactions in mid-June 2025, pursuant to a Rule 10b5-1 trading plan.

Summary

• Mark W. Haushill, EVP & CFO of Skyward Specialty Insurance Group, Inc. (SKWD), reported two sales of common stock.
• On June 13, 2025, Mr. Haushill sold 52,748 shares of common stock at a weighted average price of $58.7621 per share, with prices ranging from $58.34 to $59.23.
• On June 16, 2025, an additional 10,566 shares were sold at a weighted average price of $59.0677 per share, with prices ranging from $58.98 to $59.42.
• Both sales were executed pursuant to a Rule 10b5-1 trading plan adopted by Mr. Haushill on March 12, 2025.
• Prior to these sales, on June 6, 2025, Mr. Haushill acquired 231 shares of the Issuer's Common Stock through the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan (ESPP) for the purchase period of December 1, 2024, through May 31, 2025.
• Following the June 13, 2025 transaction, Mr. Haushill beneficially owned 133,629 shares of common stock.
• After the June 16, 2025 transaction, Mr. Haushill's beneficial ownership decreased to 123,063 shares of common stock.

Sentiment

Score: 6

Explanation: The sentiment is neutral to slightly negative. While insider selling can be viewed negatively, the fact that it was conducted under a Rule 10b5-1 plan mitigates concerns, as it indicates a pre-planned transaction for personal financial management rather than a reaction to adverse company news. The acquisition of shares via ESPP is a minor positive.

Positives

• The acquisition of 231 shares through the Employee Stock Purchase Plan (ESPP) indicates continued participation in employee ownership programs.

Negatives

• The Executive Vice President and CFO sold a significant number of shares (63,314 shares in total), which could be perceived as a reduction in insider confidence, even if pre-planned.

Future Outlook

This Form 4 filing does not contain any forward-looking statements or guidance regarding the company's future outlook.

Industry Context

This filing is a routine disclosure of insider trading activity and does not provide broader industry context or trends. It reflects an individual executive's share transactions within the insurance sector.

Stakeholder Impact

• Shareholders: May observe a reduction in direct insider ownership, which could be interpreted differently depending on individual investment philosophies. The pre-planned nature of the sales (10b5-1 plan) generally reduces negative implications.

Key Dates

Keywords

Skyward Specialty Insurance Group, SKWD, Form 4, Insider Trading, Share Sale, Executive Compensation, Mark W. Haushill, Rule 10b5-1 Plan, Employee Stock Purchase Plan