Insider Cluster (2 insiders) ·Filed May 20, 2026

HIPO

Hippo Holdings Inc.
NEUTRAL
Impact 3/10
Horizondays Processed5mo ago
Insider cluster: 2 insiders, $231K total
Actionable Insight • Neutral

Insider selling is too small to warrant action. Monitor for any larger cluster or insider buying to confirm sentiment. The company's next quarterly filing will provide more signal on fundamentals.

DirectionNeutral
Confidencehigh
Horizondays
Final — all horizons settled through T+60d
HIPO ▲ +27.13% at T+60d
NEUTRAL call ✓ call won +27.13% · α vs SPY +22.12% · entry $25.99 → $33.04
Entry anchored
May 19, 2026
via day open
T+1d
-0.15%
call -0.15% · α -0.35%
$25.95
settled 5mo ago
T+5d
-0.77%
call -0.77% · α -2.57%
$25.79
settled 5mo ago
T+20d
-0.12%
call -0.12% · α -0.86%
$25.96
settled 4mo ago
T+60d
+27.13%
call +27.13% · α +22.12%
$33.04
settled 2mo ago

Price Chart

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Executive Summary

Two insiders at Hippo Holdings sold a total of $231K in open-market sales within a week, including the CEO and the CEO of Spinnaker. The dollar amount is 0.03% of market cap — trivial relative to the $693M company. Tax-withholding transactions (non-cash) also occurred but carry no economic signal. The cluster is small and likely driven by routine portfolio management or blackout-window timing, not a coordinated bearish view.

Key Financial Metrics

Direction
selling
Total Value
$231.0K
Insiders
2

Key Facts

  • CEO Richard McCathron sold 5,000 shares for $136K on 2026-05-11.
  • CEO Spinnaker Torben Ostergaard sold 3,667 shares for $96K on 2026-05-15.
  • Total open-market sales: $231K, or 0.03% of $693M market cap.
  • Tax-withholding transactions (1,340 + 4,169 + 8,779 shares) are non-cash and not informative.
  • CFO Guy Zeltser received a grant of 743 shares on 2026-05-14 — no cash involved.
  • No 10b5-1 plan disclosure; sales are small and isolated.

Financial Impact

Total open-market sales of $231K represent 0.03% of market cap — immaterial.

insider ownership

Risk Factors

  • Insider selling could accelerate if fundamentals deteriorate, but current level is routine.
  • No material risk from this cluster alone.

Market Snapshot

Exchange
OTC
Sector
Fire, Marine & Casualty Insurance
Analyst Consensus
73% bullish (11 analysts)

Investment Themes

Traditional Finance

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-HIPO-1779236699613
6 reports for HIPO
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for HIPO — sortable, filterable
TypeNow
Aug 27, 2026
7w ago
Press Release
BULLISH ★ 7/10
$32.61 $30.24▼ −7.27%▼ −6.76%$35.28 (+8.19%)
Aug 18, 2026
8w ago
Insider Cluster
NEUTRAL ★ 2/10
$32.64 $32.00▼ −1.96%▼ −0.01%$35.28 (+8.09%)
Aug 10, 2026
9w ago
144
NEUTRAL ★ 2/10
$32.43 $32.12▼ −0.96%▲ +0.10%$35.28 (+8.79%)
Jun 15, 2026
17w ago
8-K
NEUTRAL ★ 2/10
$25.86 $28.52▲ +10.29%▲ +10.09%$35.28 (+36.43%)
May 20, 2026
21w ago
Insider Cluster
NEUTRAL ★ 3/10
$25.99 $25.96▼ −0.12%▼ −0.86%$35.28 (+35.74%)
Feb 25, 2026
33w ago
8-K
BULLISH ★ 7/10
$27.44 $25.86▼ −5.76%▼ −0.52%$35.28 (+28.57%)
Showing 6 of 6

US Market Status

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Report published May 20, 2026