DOCN DigitalOcean Holdings, Inc.

BEARISH Impact: 8/10 Insider Cluster (4 insiders)
Horizon days Filed May 21, 2026 Processed 19d 7h ago
Insider cluster: 4 insiders, $500.3M total
Latest settled — T+5d
DOCN ▲ +9.46% at T+5d
SHORT call ✗ call lost -9.46% · α vs SPY -7.80% · entry $158.46 → $173.45
Next anchor: T+20d in 12d
Last close $169.32 (close Jun 8) · -6.85% from $158.46 entry (call sign-flipped)
Entry anchored
May 21, 2026
via day open
T+1d
+1.43%
call -1.43% · α -0.84%
$160.72
settled 19d ago
T+5d
+9.46%
call -9.46% · α -7.80%
$173.45
settled 12d ago
T+20d
call — · α —
in 12d
T+60d
call — · α —
in 2mo

Price Chart

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Executive Summary

A massive insider selling cluster at DigitalOcean, led by 10% owner Access Industries selling $492.8M (3.28M shares at ~$150.30), alongside CFO Matt Steinfort ($3.8M), Director Hilary Schneider ($678K), and Director Warren Jenson ($2.95M after derivative exercise). Total disclosed sales of ~$500M represent ~3% of market cap — an extremely rare and material concentration of selling from both a controlling shareholder and top executives within a one-week window.

Key Financial Metrics

Direction
selling
Total Value
$500.3M
Insiders
4

Actionable Insight

The combination of a controlling 10% owner (Access Industries) liquidating nearly $500M alongside the CFO and two directors within the same week is a powerful negative signal. This is not routine diversification — it suggests insiders with the deepest knowledge of the business are aggressively reducing exposure. Traders should watch for an 8-K or earnings pre-announcement in the coming weeks, as such concentrated selling often precedes material negative news. The cross-filing amplifier verdicts (cluster-insider-trades + cluster-offering-context, cluster-insider-trades + cluster-press-context) further elevate the signal's significance.

Key Facts

  • Access Industries (10% owner) sold 3.28M shares for $492.83M on May 13, 2026 — the dominant trade in the cluster
  • CFO Matt Steinfort sold 25,000 shares for $3.81M on May 15, 2026
  • Director Hilary Schneider sold 4,338 shares for $678K on May 15, 2026
  • Director Warren Jenson exercised derivatives and immediately sold 20,000 shares for $2.95M on May 19, 2026
  • Total cluster value of ~$500M represents ~3% of DOCN's $16.7B market cap — far exceeding the 2% materiality threshold
  • Prior 30-day insider activity already showed 6 sells totaling $502.6M, making this a continuation of heavy selling

Financial Impact

Total insider sales of ~$500M, or ~3% of market cap, concentrated in a 7-day window

dilutionmarket_sentimentownership_concentration

Risk Factors

  • Potential undisclosed negative catalyst (earnings miss, guidance cut, or strategic setback) that insiders are front-running
  • Access Industries' selling may signal loss of confidence in DigitalOcean's growth trajectory or competitive position
  • Continued insider selling could pressure the stock further as the market prices in adverse selection
  • Historical calibration shows score-8 filings in this segment have only a 24% probability of positive T+20 alpha, with mean loss of -11.9% on losing trades

Market Snapshot

Exchange
NYSE
Sector
Services-Computer Programming, Data Processing, Etc.
Analyst Consensus
76% bullish (21 analysts)

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DOCN-1779395932533
5 reports for DOCN
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for DOCN — sortable, filterable
Type Now
May 21, 2026
19d ago
Insider Cluster
BEARISH ★ 8/10
$158.46 $173.45▼ −9.46%▼ −7.80%$169.32 (−6.85%)
May 19, 2026
21d ago
144
NEUTRAL ★ 2/10
$150.02 $152.57▲ +1.70%▼ −0.55%$169.32 (+12.86%)
May 15, 2026
25d ago
144
NEUTRAL ★ 2/10
$154.87 $158.46▲ +2.32%▲ +1.35%$169.32 (+9.33%)
Apr 24, 2026
6w ago
DEFA14A
NEUTRAL ★ 2/10
$98.95 $108.81▲ +9.96%▲ +9.56%$169.32 (+71.12%)
Mar 2, 2026
14w ago
Insider Cluster
BEARISH ★ 6/10
$58.24 $57.53▲ +1.22%▲ +0.01%$169.32 (−190.73%)
Showing 5 of 5

US Market Status

Market Closed — Opens in 9h 23m

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