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Insider Cluster (2 insiders) ·Filed Mar 3, 2026

LMND

Lemonade, Inc.
NEUTRAL
Impact 3/10
Horizondays Processed7mo ago
Insider cluster: 2 insiders, $100K total
Actionable Insight • Neutral

The sales are small in absolute and relative terms and likely represent routine portfolio management. No immediate concern, but continued selling by executives could signal waning confidence.

DirectionNeutral
Confidencehigh
Horizondays
Final — all horizons settled through T+60d
LMND ▲ +9.20% at T+60d
NEUTRAL call +9.20% · α vs SPY -1.12% · entry $51.86 → $56.63
Entry = T+0 close
Mar 2, 2026
via day close
T+1d
+5.61%
call +5.61% · α +4.85%
$54.77
settled 8mo ago
T+5d
+6.88%
call +6.88% · α +7.36%
$55.43
settled 8mo ago
T+20d
+20.86%
call +20.86% · α +25.27%
$62.68
settled 7mo ago
T+60d
+9.20%
call +9.20% · α -1.12%
$56.63
settled 5mo ago

Price Chart

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Executive Summary

Two C-suite executives at Lemonade sold shares in the past week, with Chief Insurance Officer John Sheldon selling a total of 5,344 shares for $276,340. The sales were open-market transactions and represent a small fraction of the company's market cap.

Key Financial Metrics

Direction
selling
Total Value
$287.5K
Insiders
2

Key Facts

  • Chief Insurance Officer John Sheldon sold 5,344 shares in two transactions on March 3 and March 4, 2026, totaling $276,340.
  • Chief Business Officer Maya Prosor sold 223 shares on March 3, 2026, for $11,177.
  • All transactions were open-market sales (code S), not related to derivatives, taxes, or gifts.
  • Total value of the cluster: $287,517, representing approximately 0.0068% of Lemonade's $4.2B market cap.

Financial Impact

$287,517 in total insider sales over 7 days

insider ownershipshare count

Risk Factors

  • If additional sales emerge, it could indicate broader concern among insiders.
  • Open-market sales by multiple C-suite members, while small, may be perceived negatively by sentiment-sensitive traders.

Market Snapshot

Exchange
NYSE

Investment Themes

Traditional Finance

Documents Analyzed

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

DocumentAccession Number
CONTEXT: Insider Cluster Data (3 trades, 7d window)cluster-LMND-1772751289760
18 reports for LMND
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for LMND — sortable, filterable
TypeNow
Oct 19, 2026
7d ago
Press Release
NEUTRAL ★ 1/10
$43.15awaiting T+20—$45.08 (+4.47%)
Oct 15, 2026
11d ago
8-K/A
NEUTRAL ★ 2/10
$44.20awaiting T+20—$45.08 (+1.99%)
Sep 8, 2026
6w ago
Insider Cluster
NEUTRAL ★ 3/10
$49.22 $46.83▼ −4.86%▼ −6.80%$45.08 (−8.41%)
Sep 3, 2026
7w ago
144
NEUTRAL ★ 2/10
$55.08 $45.14▼ −18.05%▼ −16.93%$45.08 (−18.16%)
Aug 7, 2026
11w ago
Press Release
BULLISH ★ 5/10
$52.68 $50.55▼ −4.04%▼ −3.13%$45.08 (−14.43%)
Jul 16, 2026
14w ago
Press Release
NEUTRAL ★ 1/10
$67.18 $52.64▼ −21.64%▼ −26.09%$45.08 (−32.90%)
Jul 9, 2026
15w ago
Insider Cluster
BEARISH ★ 4/10
$70.33 $51.86▲ +26.26%▲ +28.50%$45.08 (+35.90%)
Jun 12, 2026
19w ago
Institutional Cluster
MIXED ★ 5/10
$57.49 $70.51▲ +22.65%▲ +20.87%$45.08 (−21.59%)
Jun 9, 2026
19w ago
Press Release
NEUTRAL ★ 2/10
$53.58 $77.59▲ +44.81%▲ +43.37%$45.08 (−15.86%)
Jun 5, 2026
20w ago
Insider Cluster
NEUTRAL ★ 2/10
$52.97 $78.70▲ +48.57%▲ +46.94%$45.08 (−14.90%)
Showing 10 of 18

US Market Status

Market Closed — Opens Wed (10h 58m)

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Report published Mar 5, 2026