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Insider Cluster (7 insiders) ·Filed Feb 27, 2026

SKWD

Skyward Specialty Insurance Group, Inc.
BULLISH
Impact 7/10
Horizonweeks Processed7mo ago
Insider cluster: 2 insiders, $509K total
Actionable Insight ▲ Bullish

The CEO's substantial personal purchase is a strong vote of confidence, especially in a stable or down market. Traders should watch for follow-on buying and any upcoming earnings commentary.

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

Skyward Specialty executives, including CEO Andrew Robinson and CFO Mark Haushill, engaged in a cluster of insider transactions over the past week. The key activity was open-market share purchases totaling over $650K by the CEO and Apollo's CFO, signaling confidence, while other executives had routine tax-related share withholdings and option exercises with no cash impact.

Key Financial Metrics

Direction
buying
Total Value
$659.7K
Insiders
7

Key Facts

  • CEO Andrew Robinson purchased $503,934 worth of shares in the open market.
  • Apollo's CFO Taryn McHarg bought $4,671 of SKWD shares, signaling external confidence.
  • Total open-market purchases in the cluster: $659,665.
  • Multiple executives exercised stock options and had shares withheld for taxes, a routine non-cash event.
  • No open-market sales occurred in the cluster.

Financial Impact

$659,665 in net insider buying over 7 days, representing 0.033% of $2.0B market cap

insider sentimentmarket confidence

Risk Factors

  • The dollar amount, while meaningful, is still small relative to market cap (<0.1%)
  • Tax withholdings and option exercises are routine and should not be interpreted as sentiment signals

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 (15 trades, 7d window)cluster-SKWD-1772561399210
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
6d ago
Institutional Cluster
BULLISH ★ 4/10
$62.16awaiting T+60—$60.13 (−3.27%)
Aug 20, 2026
9w ago
8-K
NEUTRAL ★ 3/10
$55.86awaiting T+60—$60.13 (+7.64%)
Aug 7, 2026
11w ago
3
NEUTRAL ★ 1/10
$62.00awaiting T+60—$60.13 (−3.02%)
Jul 15, 2026
14w ago
8-K
NEUTRAL ★ 3/10
$58.47 $58.32▼ −0.26%▼ −3.97%$60.13 (+2.84%)
Jun 12, 2026
19w ago
Institutional Cluster
MIXED ★ 4/10
$50.05 $56.53▲ +12.95%▲ +9.68%$60.13 (+20.14%)
Jun 11, 2026
19w ago
Institutional Cluster
MIXED ★ 3/10
$50.80 $57.34▲ +12.87%▲ +8.48%$60.13 (+18.37%)
May 6, 2026
24w ago
8-K
BULLISH ★ 6/10
$45.51 $60.87▲ +33.75%▲ +29.92%$60.13 (+32.12%)
May 6, 2026
24w ago
Press Release
BULLISH ★ 7/10
$45.51 $60.87▲ +33.75%▲ +29.92%$60.13 (+32.12%)
Mar 25, 2026
30w ago
DEFA14A
NEUTRAL ★ 3/10
$43.15 $51.02▲ +18.23%▲ +4.77%$60.13 (+39.35%)
Feb 27, 2026
34w ago
Insider Cluster
BULLISH ★ 7/10
$48.58 $45.79▼ −5.74%▼ −15.08%$60.13 (+23.78%)
Showing 10 of 12

US Market Status

Market Closed — Opens Thu (12h 2m)

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Report published Mar 3, 2026