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Insider Cluster (12 insiders) ·Filed Feb 27, 2026

SKWD

Skyward Specialty Insurance Group, Inc.
BULLISH
Impact 7/10
Horizonweeks Processed7mo ago
Insider cluster: 3 insiders, $0.6M total
Actionable Insight ▲ Bullish

The concentrated buying by the CEO and senior executives suggests strong confidence in near-term prospects; traders should watch for upcoming earnings or strategic updates that may confirm improving fundamentals.

DirectionBullish
Confidencehigh
Horizonweeks
Final — all horizons settled through T+60d ⚠ clustered
SKWD ▼ -5.74% at T+60d
LONG call ✗ call lost -5.74% · α vs SPY -15.08% · entry $48.58 → $45.79
Entry = T+0 close
Feb 27, 2026
via day close
T+1d
-0.74%
call -0.74% · α +0.14%
$48.22
settled 8mo ago
T+5d
-4.78%
call -4.78% · α -3.59%
$46.26
settled 8mo ago
T+20d
-9.98%
call -9.98% · α -2.06%
$43.73
settled 7mo ago
T+60d
-5.74%
call -5.74% · α -15.08%
$45.79
settled 5mo ago

Price Chart

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Executive Summary

Multiple Skyward Specialty executives, including CEO Andrew Robinson and other C-suite leaders, made open-market share purchases totaling $804,818 over the past week, signaling strong insider confidence. These buying activities were partially offset by routine tax withholding transactions involving share surrenders worth $579,763, which are non-cash events and not indicative of sentiment.

Key Financial Metrics

Direction
buying
Total Value
$804.8K
Insiders
12

Key Facts

  • CEO Andrew S. Robinson purchased 10,821 shares for $503,934 in an open-market transaction.
  • Three other executives (Kuczinski, Peirce, McHarg) made additional open-market purchases totaling $299,474.
  • Total open-market buying: $804,818 across 6 transactions by 4 insiders.
  • Six tax withholding transactions (codes F) totaled $579,763 but represent non-cash share surrenders to cover taxes, not selling sentiment.
  • Cluster occurs within a 7-day window and represents ~0.04% of Skyward's $2.0B market cap.

Financial Impact

$804,818 in net insider buying over 7 days

insider sentimentmarket confidence

Risk Factors

  • The dollar amount, while meaningful, is still small relative to market cap (~0.04%), limiting broad market impact.
  • Recent tax withholding transactions could create misleading perception of selling pressure if misinterpreted.

Market Snapshot

Exchange
Nasdaq

Investment Themes

Traditional Finance

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

DocumentAccession Number
CONTEXT: Insider Cluster Data (12 trades, 7d window)cluster-SKWD-1772651087449
12 reports for SKWD
Performance horizon
50% Hit rate @ T+60 2 of 4 directional calls Went positive at some point 2 of 5 best @ T+60▲ +33.75%May 6, 2026
Filters
Rows
Reports for SKWD — sortable, filterable
TypeNow
Oct 21, 2026
5d ago
Institutional Cluster
BULLISH ★ 4/10
$62.16awaiting T+60—$58.78 (−5.45%)
Aug 20, 2026
9w ago
8-K
NEUTRAL ★ 3/10
$55.86awaiting T+60—$58.78 (+5.22%)
Aug 7, 2026
11w ago
3
NEUTRAL ★ 1/10
$62.00awaiting T+60—$58.78 (−5.20%)
Jul 15, 2026
14w ago
8-K
NEUTRAL ★ 3/10
$58.47 $58.32▼ −0.26%▼ −3.97%$58.78 (+0.52%)
Jun 12, 2026
19w ago
Institutional Cluster
MIXED ★ 4/10
$50.05 $56.53▲ +12.95%▲ +9.68%$58.78 (+17.43%)
Jun 11, 2026
19w ago
Institutional Cluster
MIXED ★ 3/10
$50.80 $57.34▲ +12.87%▲ +8.48%$58.78 (+15.70%)
May 6, 2026
24w ago
8-K
BULLISH ★ 6/10
$45.51 $60.87▲ +33.75%▲ +29.92%$58.78 (+29.15%)
May 6, 2026
24w ago
Press Release
BULLISH ★ 7/10
$45.51 $60.87▲ +33.75%▲ +29.92%$58.78 (+29.15%)
Mar 25, 2026
30w ago
DEFA14A
NEUTRAL ★ 3/10
$43.15 $51.02▲ +18.23%▲ +4.77%$58.78 (+36.21%)
Feb 27, 2026
34w ago
Insider Cluster
BULLISH ★ 7/10
$48.58 $45.79▼ −5.74%▼ −15.08%$58.78 (+20.99%)
Showing 10 of 12

US Market Status

Market Open — Closes in 2h 38m

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Report published Mar 4, 2026