CEO Andrew S. Robinson buys $1 million of Skyward Specialty Insurance Group, Inc. (SKWD)

Andrew S. Robinson, chief executive of Skyward Specialty Insurance Group, Inc., bought 22,100 shares on the open market on February 27, 2026 at an average of $46.76 a share, for a total of $1 million. The purchase was reported to the SEC on Form 4 on February 27, 2026.

It raised their holding by 15%, to 167,674 shares.

The purchase came after a fall: Skyward Specialty Insurance Group, Inc. stock was down 3.2% over the 13 weeks before.

2 other insiders also bought at least $10,000 of SKWD within 30 days, which makes this a cluster buy.

In the 12 months up to this filing, Skyward Specialty Insurance Group, Inc. insiders reported 1 open-market purchase and 0 sales.

WallStPal Score: 60 out of 100, because of a large purchase; 2 other insiders also bought; bought by a top executive.

What happened next: after 1 month the stock was down 11.8% (5.9 points worse than the S&P 500); after 6 months the stock was up 21.7% (10.6 points better than the S&P 500). Based on weekly prices from the week of the purchase.

Our read

The first open-market purchase by Andrew S. Robinson in our records. It is worth reading next to the company's own results and news before drawing conclusions.

Source: SEC Form 4 filing ↗. This story was written automatically from the filing and weekly price data. Information, not investment advice.

Examples

Big insider purchases have made news before. In January 2016, with bank stocks falling, JPMorgan Chase CEO Jamie Dimon bought 500,000 JPMorgan shares, about $26 million of his own money, and the purchase was widely reported as a sign of confidence.

Explain it like I'm 13

Andrew S. Robinson helps run Skyward Specialty Insurance Group, Inc.. Spending $1 million of their own money on the company's stock is like a coach buying a big stack of tickets to their own team's games: it suggests they think the team will do well. It is not a promise, and insiders can be wrong.

More: all SKWD insider trades · Andrew S. Robinson's track record