SecBot SecBot
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, $655K total
Actionable Insight ▲ Bullish

The CEO's significant personal purchase suggests strong conviction ahead of potential catalysts — monitor upcoming earnings or strategic updates. Tax-related share surrenders are routine and should not be interpreted as negative.

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

Loading chart...

Executive Summary

Skyward Specialty CEO and another insider made open-market purchases totaling $655K, signaling confidence, while several executives including the CEO and CFO surrendered shares for tax withholding following a routine option exercise. The buying activity is material and offsets neutral tax-related selling.

Key Financial Metrics

Direction
buying
Total Value
$655.3K
Insiders
7

Key Facts

  • CEO Andrew S. Robinson purchased $504K in shares on open market at $46.57 per share.
  • Christopher Locke, another insider, bought $151K in shares at $47.30.
  • Total open-market buying: $655K (0.03% of $2.0B market cap).
  • CEO and CFO, along with other executives, exercised stock options and surrendered shares to cover taxes — these are non-cash, pre-scheduled events worth $539K in total value surrendered.
  • No open-market sales by insiders; all selling was tax-related and tied to option exercises.

Financial Impact

$655,000 in net insider buying from open-market purchases, partially offset by $539,000 in tax withholding sales. Net positive inflow of economic confidence.

insider sentimentshareholder confidence

Risk Factors

  • The purchases, while meaningful, represent a small fraction of market cap (<0.04%) and may not signal broad-based optimism beyond top leadership.
  • No other C-suite members participated in open-market buying beyond the CEO.

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 (14 trades, 7d window)cluster-SKWD-1772551218994
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—$58.59 (−5.74%)
Aug 20, 2026
9w ago
8-K
NEUTRAL ★ 3/10
$55.86awaiting T+60—$58.59 (+4.89%)
Aug 7, 2026
11w ago
3
NEUTRAL ★ 1/10
$62.00awaiting T+60—$58.59 (−5.50%)
Jul 15, 2026
14w ago
8-K
NEUTRAL ★ 3/10
$58.47 $58.32▼ −0.26%▼ −3.97%$58.59 (+0.21%)
Jun 12, 2026
19w ago
Institutional Cluster
MIXED ★ 4/10
$50.05 $56.53▲ +12.95%▲ +9.68%$58.59 (+17.06%)
Jun 11, 2026
19w ago
Institutional Cluster
MIXED ★ 3/10
$50.80 $57.34▲ +12.87%▲ +8.48%$58.59 (+15.33%)
May 6, 2026
24w ago
8-K
BULLISH ★ 6/10
$45.51 $60.87▲ +33.75%▲ +29.92%$58.59 (+28.74%)
May 6, 2026
24w ago
Press Release
BULLISH ★ 7/10
$45.51 $60.87▲ +33.75%▲ +29.92%$58.59 (+28.74%)
Mar 25, 2026
30w ago
DEFA14A
NEUTRAL ★ 3/10
$43.15 $51.02▲ +18.23%▲ +4.77%$58.59 (+35.78%)
Feb 27, 2026
34w ago
Insider Cluster
BULLISH ★ 7/10
$48.58 $45.79▼ −5.74%▼ −15.08%$58.59 (+20.61%)
Showing 10 of 12

US Market Status

Market Closed — Opens Thu (11h 51m)

Subscribe to SecBot

Get Real-Time SEC Filing Intelligence

Comprehensive SEC filing analysis delivered the moment filings hit EDGAR. Sentiment scoring, impact analysis, and actionable insights for every material event.

Create a free account Live analysis, Telegram alerts, watchlists and the MCP server for subscribers
Report published Mar 3, 2026