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Insider Cluster (2 insiders) ·Filed Sep 23, 2026

DDOG

Datadog, Inc.
BEARISH
Impact 4/10
Horizondays Processed1mo ago
Insider cluster: 2 insiders, $2.5M total
Actionable Insight ▼ Bearish

The CFO's $2.41M open-market sale without a disclosed 10b5-1 plan is the dominant signal here. While the dollar amount is small relative to market cap, the seniority of the seller and lack of plan disclosure warrant monitoring for any upcoming negative news or earnings pre-announcement.

DirectionBearish
Confidencemedium
Horizondays
Latest settled — T+20d
DDOG ▲ +0.32% at T+20d
SHORT call ✗ call lost -0.32% · α vs SPY -0.74% · entry $256.92 → $257.75
Next anchor: T+60d in 7w
Latest observation: T+21 -11.92% FF3 residual α
Entry = T+0 close
Sep 23, 2026
via day close
T+1d
+4.36%
call -4.36% · α -3.82%
$268.13
settled 5w ago
T+5d
+7.61%
call -7.61% · α -8.02%
$276.46
settled 27d ago
T+20d
+0.32%
call -0.32% · α -0.74%
$257.75
settled 6d ago
T+60d
Pending
in 7w

Price Chart

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Executive Summary

CFO David Obstler sold $2.41M worth of DDOG shares and the General Counsel sold $44K in a cluster totaling $2.46M. The CFO sale is a large open-market disposition by a top executive, which typically carries negative signaling weight, though the total represents only ~0.01% of Datadog's market cap, making it immaterial relative to company size.

Key Financial Metrics

Direction
selling
Total Value
$2.5M
Insiders
2

Key Facts

  • CFO David Obstler sold 10,000 shares at $241.25 for $2.41M on 2026-09-21
  • General Counsel Kerry Acocella sold 200 shares at $221.63 for $44K on 2026-09-14
  • Total insider sales: $2.46M over 7-day window
  • No 10b5-1 plan indicated for either sale
  • Sales represent approximately 0.01% of Datadog's market cap

Financial Impact

Insider sales of $2.46M, negligible relative to market cap

insider ownership

Risk Factors

  • CFO selling without a 10b5-1 plan could signal near-term bearish sentiment
  • Cluster sales by two officers may indicate coordinated insider pessimism

Investment Themes

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DDOG-1790196647274
79 reports for DDOG
Performance horizon
50% Hit rate @ T+1 9 of 18 directional calls Went positive at some point 13 of 18 best @ T+60▲ +105.85%Apr 23, 2026
Filters
Rows
Reports for DDOG — sortable, filterable
TypeNow
Oct 20, 2026
7d ago
Institutional Cluster
BULLISH ★ 4/10
$273.09 $257.75▼ −5.62%▼ −4.44%$280.82 (+2.83%)
Oct 19, 2026
8d ago
ANALYST-UPGRADE
MIXED ★ 6/10
$260.36 $256.43▼ −1.51%▼ −1.84%$280.82 (+7.86%)
Oct 7, 2026
20d ago
144
NEUTRAL ★ 3/10
$273.80 $293.26▲ +7.11%▲ +6.51%$280.82 (+2.56%)
Sep 25, 2026
4w ago
Insider Cluster
BEARISH ★ 5/10
$268.70 $268.56▲ +0.05%▼ −0.13%$280.82 (−4.51%)
Sep 23, 2026
4w ago
Insider Cluster
BEARISH ★ 4/10
$256.92 $268.13▼ −4.36%▼ −3.82%$280.82 (−9.30%)
Sep 16, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$236.00 $229.92▲ +2.58%▲ +2.46%$280.82 (−18.99%)
Sep 15, 2026
6w ago
Insider Cluster
NEUTRAL ★ 3/10
$230.79 $236.00▲ +2.26%▲ +1.12%$280.82 (+21.68%)
Sep 10, 2026
6w ago
Insider Cluster
BEARISH ★ 4/10
$221.21 $230.05▼ −4.00%▼ −4.44%$280.82 (−26.95%)
Sep 9, 2026
6w ago
Insider Cluster
BEARISH ★ 6/10
$221.72 $221.21▲ +0.23%▲ +1.08%$280.82 (−26.66%)
Sep 8, 2026
7w ago
Insider Cluster
NEUTRAL ★ 3/10
$225.27 $221.72▼ −1.58%▼ −0.98%$280.82 (+24.66%)
Showing 10 of 79

US Market Status

Market Closed — Opens Wed (< 1m)

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Report published Sep 23, 2026