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Insider Cluster (4 insiders) ·Filed Sep 16, 2026

DDOG

Datadog, Inc.
BEARISH
Impact 5/10
Horizonweeks Processed1mo ago
Insider cluster: 4 insiders, $3.8M total
Actionable Insight ▼ Bearish

The CEO's $2.20M sale at $204.03 is the most significant trade — it is below the current trading range (~$220), which may indicate a lack of conviction at current levels. Monitor upcoming earnings (likely late Oct/early Nov) for any guidance revision or operational softness that could explain the cluster.

DirectionBearish
Confidencemedium
Horizonweeks
Latest settled — T+20d
DDOG ▲ +12.82% at T+20d
SHORT call ✗ call lost -12.82% · α vs SPY -11.61% · entry $236.00 → $266.25
Next anchor: T+60d in 6w
Latest observation: T+26 -11.88% FF3 residual α
Entry = T+0 close
Sep 16, 2026
via day close
T+1d
-2.58%
call +2.58% · α +2.46%
$229.92
settled 6w ago
T+5d
+8.86%
call -8.86% · α -8.26%
$256.92
settled 5w ago
T+20d
+12.82%
call -12.82% · α -11.61%
$266.25
settled 13d ago
T+60d
Pending
in 6w

Price Chart

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Executive Summary

Four Datadog insiders, including the CEO, CFO, and Chief Revenue Officer, sold a total of $3.81M in open-market sales over a one-week window. The CEO's sale of $2.20M is the largest single trade, and the cluster is concentrated among top C-suite executives, which elevates the signal beyond routine diversification.

Key Financial Metrics

Direction
selling
Total Value
$3.8M
Insiders
4

Key Facts

  • Total insider sales: $3.81M across 4 insiders in a 7-day window
  • CEO Olivier Pomel sold 10,800 shares for $2.20M at $204.03
  • CFO David Obstler sold 2,700 shares for $588K at $221.24
  • Chief Revenue Officer Sean Walters sold 4,286 shares for $949K at $221.40
  • Chief Product Officer Yanbing Li sold 300 shares for $67K at $223.03
  • All trades are open-market sales (code S); no 10b5-1 plan indicated
  • Total sales represent approximately 0.1% of market cap (~$38B)

Financial Impact

Insider sales of $3.81M represent ~0.1% of market cap, but the concentration among the CEO, CFO, and CRO makes this notable

insider ownershipmarket sentiment

Risk Factors

  • CEO selling $2.20M at a price below the cluster's average suggests possible concern about near-term valuation
  • No 10b5-1 plan disclosed for any of the sales, increasing the likelihood of discretionary selling

Investment Themes

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DDOG-1789592532375
79 reports for DDOG
Performance horizon
44% Hit rate @ T+1 8 of 18 directional calls Went positive at some point 12 of 18 best @ T+60▲ +105.85%Apr 23, 2026
Filters
Rows
Reports for DDOG — sortable, filterable
TypeNow
Oct 20, 2026
6d ago
Institutional Cluster
BULLISH ★ 4/10
$273.09 $257.75▼ −5.62%▼ −4.44%$280.24 (+2.62%)
Oct 19, 2026
7d ago
ANALYST-UPGRADE
MIXED ★ 6/10
$260.36 $256.43▼ −1.51%▼ −1.84%$280.24 (+7.64%)
Oct 7, 2026
19d ago
144
NEUTRAL ★ 3/10
$273.80 $293.26▲ +7.11%▲ +6.51%$280.24 (+2.35%)
Sep 25, 2026
4w ago
Insider Cluster
BEARISH ★ 5/10
$268.70 $268.56▲ +0.05%▼ −0.13%$280.24 (−4.29%)
Sep 23, 2026
4w ago
Insider Cluster
BEARISH ★ 4/10
$256.92 $268.13▼ −4.36%▼ −3.82%$280.24 (−9.08%)
Sep 16, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$236.00 $229.92▲ +2.58%▲ +2.46%$280.24 (−18.75%)
Sep 15, 2026
5w ago
Insider Cluster
NEUTRAL ★ 3/10
$230.79 $236.00▲ +2.26%▲ +1.12%$280.24 (+21.43%)
Sep 10, 2026
6w ago
Insider Cluster
BEARISH ★ 4/10
$221.21 $230.05▼ −4.00%▼ −4.44%$280.24 (−26.69%)
Sep 9, 2026
6w ago
Insider Cluster
BEARISH ★ 6/10
$221.72 $221.21▲ +0.23%▲ +1.08%$280.24 (−26.39%)
Sep 8, 2026
6w ago
Insider Cluster
NEUTRAL ★ 3/10
$225.27 $221.72▼ −1.58%▼ −0.98%$280.24 (+24.40%)
Showing 10 of 79

US Market Status

Market Closed — Opens Wed (10h 16m)

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Report published Sep 16, 2026