144 ·Filed Jun 2, 2026

DDOG

Datadog, Inc.
NEUTRAL
Impact 2/10
Horizondays Processed4mo ago SEC0001561550-26-000157
Form 144 — notice of proposed sale of securities
Actionable Insight • Neutral

This is a routine post-vesting sale by an officer, not a material insider signal. Monitor for any subsequent Form 4 filings to confirm execution, but no immediate trading action is warranted.

DirectionNeutral
Confidencemedium
Horizondays
Latest settled — T+20d ⚠ clustered
DDOG ▲ +4.01% at T+20d
NEUTRAL call ✓ call won +4.01% · α vs SPY +5.01% · entry $250.33 → $260.36
Next anchor: T+60d due 5w ago
Latest observation: T+58 -77.30% FF3 residual α
Entry anchored
Jun 2, 04:33 PM ET
via exchange tick
T+1d
-2.69%
call -2.69% · α -3.09%
$243.60
settled 4mo ago
T+5d
-9.07%
call -9.07% · α -5.25%
$227.63
settled 4mo ago
T+20d
+4.01%
call +4.01% · α +5.01%
$260.36
settled 3mo ago
T+60d
—
call — · α —
—
due 5w ago

Price Chart

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Executive Summary

David Obstler, an officer of Datadog, filed a Form 144 notice of intent to sell 16,031 shares of Class A Common Stock, valued at approximately $3.3 million based on the filing date. The shares were acquired through vesting of restricted stock units and performance stock units on June 1, 2026, and the sale appears to be a routine post-vesting transaction.

Key Facts

  • David Obstler (officer) filed Form 144 to sell 16,031 shares of Class A Common Stock.
  • Estimated value of proposed sale: approximately $3.3 million (based on 16,031 shares × ~$206/share).
  • Shares were acquired via vesting of restricted stock units and performance stock units on June 1, 2026.
  • Sale is intended to occur on or after June 2, 2026, on NASDAQ.
  • The filing is an advance notice of intent to sell; the actual sale may not occur.

Financial Impact

Proposed sale of 16,031 shares valued at ~$3.3 million, representing a small fraction of the officer's likely total holdings and less than 0.01% of Datadog's $98.8B market cap.

dilution

Risk Factors

  • Insider selling ahead of earnings or other catalysts could indicate reduced conviction, but this filing lacks such context.
  • Form 144 is only an intent to sell; the sale may not be executed.

Market Snapshot

Exchange
Nasdaq
Sector
Services-Prepackaged Software
Analyst Consensus
93% bullish (56 analysts)

Investment Themes

Cloud & SaaS

Documents Analyzed

This report is based on 3 SEC documents filed with EDGAR.

DocumentAccession Number
144 Filing (Primary)0001561550-26-000157
Document: 0001561550-26-000157-index.html0001561550-26-000157
Document: 0001561550-26-000157.txt0001561550-26-000157
72 reports for DDOG
Performance horizon
87% Hit rate 13 of 15 directional calls best @ T+60▲ +105.85%Apr 23, 2026
Filters
Rows
Reports for DDOG — sortable, filterable
TypeNow
Sep 15, 2026
17d ago
Insider Cluster
NEUTRAL ★ 3/10
$230.27 $230.79▲ +0.23%▲ +0.67%$278.73 (+21.04%)
Sep 10, 2026
22d ago
Insider Cluster
BEARISH ★ 4/10
$221.72 $221.21▲ +0.23%▲ +1.08%$278.73 (−25.71%)
Sep 9, 2026
23d ago
Insider Cluster
BEARISH ★ 6/10
$225.27 $221.72▲ +1.58%▲ +0.98%$278.73 (−23.73%)
Sep 4, 2026
28d ago
Insider Cluster
BEARISH ★ 4/10
$212.93 $210.23▲ +1.27%▲ +0.72%$278.73 (−30.90%)
Sep 3, 2026
29d ago
Insider Cluster
NEUTRAL ★ 2/10
$214.76 $212.93▼ −0.85%▼ −0.47%$278.73 (+29.79%)
Aug 26, 2026
5w ago
Insider Cluster
NEUTRAL ★ 3/10
$222.87 awaiting T+1awaiting T+1—$278.73 (+25.06%)
Aug 21, 2026
6w ago
Insider Cluster
NEUTRAL ★ 2/10
$235.62 $225.77▼ −4.18%▼ −3.89%$278.73 (+18.30%)
Aug 17, 2026
6w ago
Insider Cluster
NEUTRAL ★ 3/10
$247.32 $246.00▼ −0.53%▲ +0.14%$278.73 (+12.70%)
Aug 12, 2026
7w ago
Insider Cluster
NEUTRAL ★ 3/10
$240.91 $252.24▲ +4.70%▲ +4.01%$278.73 (+15.70%)
Aug 10, 2026
7w ago
Insider Cluster
NEUTRAL ★ 2/10
$246.78 $240.91▼ −2.38%▼ −2.63%$278.73 (+12.95%)
Showing 10 of 72

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