SKWD Skyward Specialty Insurance Group, Inc.

NASDAQ
$56.74

Skyward Specialty Insurance Group, Inc. (SKWD) Insider Activity

What the officers, directors and large holders did with their own shares. Only open-market purchases and sales count toward the totals — grants, option exercises and shares withheld for tax are compensation mechanics, not decisions, and they're listed separately below.

30D 90D 6M 1Y
Insider signal Bullish Insiders bought more than they sold over this window — uncommon at any size.
Cluster activity 0 buyers in the last 30 days 0 buyers in the last 90 days 0 sellers in the last 90 days
Insiders buying
4
11 transactions
Insiders selling
3
9 transactions
Purchases
$1.5M
32,500 shares
Sales
$969.1K
19,557 shares
Net activity
$558.6K
purchases less sales

How much of that selling was preplanned? 52% planned / 48% discretionary

10b5-1 plan sales $503.9K 5 transactions · 10,420 shares
Discretionary sales $465.3K 4 transactions · 9,137 shares

Largest single sale: $431.0K.

Where they traded

Buy Sell Dot area is proportional to transaction value.

Last open-market purchase: May 21, 2026 , by Kuczinski Anthony J .

Recent open-market activity

Date Insider Role Action Shares Price Value Held after
Schmitt Thomas N CPO, Skyward Group Sell 8,397 $51.32 $431.0K 10,353 −44.8% of holding
Kuczinski Anthony J 3 fills Director Buy 2,000 $47.10 $94.2K 15,977
Ashe Gena L 3 fills Director Sell 740 $46.35 $34.3K 5,210 −12.4% of holding
Kuczinski Anthony J Director Buy 1,000 $48.13 $48.1K 11,903
Peirce Christopher Locke Director Buy 3,200 $47.30 $151.4K 3,200
Kuczinski Anthony J Director Buy 2,000 $48.79 $97.6K 10,903
Robinson Andrew S 2 fills Chairman & CEO, Skyward Group Buy 22,100 $46.76 $1.0M 167,674
Kuczinski Anthony J Director Buy 2,000 $46.88 $93.8K 8,903
McHarg Taryn Leonie 2 fills CFO - Apollo Buy 200 $46.60 $9.3K 100
Schmitt Thomas N CPO, Skyward Group Sell 10b5-1 2,616 $43.49 $113.8K 14,747 −15.1% of holding
Kapadia Sandip A Head of Actuarial Sell 10b5-1 5,030 $50.01 $251.6K 8,059 −38.4% of holding
Kapadia Sandip A 2 fills Head of Actuarial Sell 10b5-1 2,686 $50.02 $134.4K 14,289 −15.8% of holding
Schmitt Thomas N CHIEF PEOPLE & ADMIN.OFFICER Sell 10b5-1 88 $47.61 $4.2K 9,959 −0.9% of holding

Form 4s are due within two business days of a transaction, so this is close to real time — unlike the quarterly 13F data on the Institutional tab. A single large sale often reflects a prearranged 10b5-1 plan rather than a fresh view, so read a pattern of sales rather than any one of them.