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Insider Cluster (6 insiders) ·Filed May 19, 2026

DBX

DROPBOX, INC.
BEARISH
Impact 5/10
Horizonweeks Processed5mo ago
Insider cluster: 2 insiders, $1.1M total
Actionable Insight ▼ Bearish

The CEO's first open-market sale since 2024 is a cautionary signal, but the dollar amount is small relative to market cap. Monitor for additional insider sales in the next 30 days; if selling continues, it would amplify the bearish read. The Q1 earnings showed a 24% net income decline, which may pressure the stock near-term.

DirectionBearish
Confidencemedium
Horizonweeks
Final — all horizons settled through T+60d ⚠ clustered
DBX ▲ +24.52% at T+60d
SHORT call ✗ call lost -24.52% · α vs SPY -19.79% · entry $27.53 → $34.28
Entry = T+0 close
May 19, 2026
via day close
T+1d
-1.34%
call +1.34% · α +1.54%
$27.16
settled 5mo ago
T+5d
-4.87%
call +4.87% · α +6.67%
$26.19
settled 5mo ago
T+20d
-4.06%
call +4.06% · α +4.02%
$26.41
settled 4mo ago
T+60d
+24.52%
call -24.52% · α -19.79%
$34.28
settled 2mo ago

Price Chart

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Executive Summary

Dropbox insiders, including CEO Andrew Houston, sold $1.08M in stock over a week following Q1 earnings that showed revenue growth but a 24% drop in net income. The CEO's $974K open-market sale after converting derivatives is the most notable signal, while other C-suite sales are partly tax-withholding related. The cluster is bearish given the CEO's material sale and deteriorating profitability.

Key Financial Metrics

Direction
selling
Total Value
$1.1M
Insiders
6

Key Facts

  • CEO Andrew Houston sold 37,498 shares for $974K on May 14 after converting derivatives at $0 cost basis.
  • Total open-market sales: $1.08M across 4 insiders (CEO, CLO, CTO, CAO, director).
  • Tax-withholding sales (non-cash) totaled $1.92M across 5 insiders, tied to vesting events.
  • Cluster follows Q1 2026 earnings (May 7): revenue $629.5M (+0.8% YoY), but GAAP net income fell 24% to $114.5M.
  • Open-market sales represent ~0.017% of $6.5B market cap, below the 0.1% materiality threshold.

Financial Impact

Open-market insider sales total $1.08M, or 0.017% of market cap — below materiality threshold. Tax-withholding sales of $1.92M are non-cash and routine.

insider sellingCEO salenet income decline

Risk Factors

  • CEO sale after derivative conversion could signal peak valuation or personal diversification needs.
  • Net income decline of 24% YoY despite revenue growth suggests margin compression or higher interest costs.
  • Paying users declining to 18.09M indicates competitive pressure from cloud storage rivals.

Market Snapshot

Exchange
Nasdaq
Sector
Services-Prepackaged Software
Analyst Consensus
6% bullish (16 analysts)

Investment Themes

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DBX-1779226706018
28 reports for DBX
Performance horizon
100% Hit rate @ T+20 5 of 5 directional calls Went positive at some point 5 of 7 best @ T+5▲ +11.40%Sep 17, 2026
Filters
Rows
Reports for DBX — sortable, filterable
TypeNow
Oct 21, 2026
4d ago
Institutional Cluster
BEARISH ★ 4/10
$37.48awaiting T+20—$37.73 (−0.67%)
Oct 19, 2026
7d ago
Insider Cluster
BEARISH ★ 4/10
$35.94awaiting T+20—$37.73 (−4.98%)
Oct 5, 2026
20d ago
Insider Cluster
NEUTRAL ★ 4/10
$33.73awaiting T+20—$37.73 (+11.86%)
Sep 17, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$36.48 $35.57▲ +2.49%▲ +2.70%$37.73 (−3.43%)
Sep 15, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$37.74 $35.62▲ +5.62%▲ +7.68%$37.73 (+0.03%)
Sep 14, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$37.63 $35.60▲ +5.39%▲ +8.37%$37.73 (−0.27%)
Sep 9, 2026
6w ago
Insider Cluster
NEUTRAL ★ 2/10
$35.05 $34.14▼ −2.60%▼ −4.97%$37.73 (+7.65%)
Aug 19, 2026
9w ago
Insider Cluster
NEUTRAL ★ 4/10
$34.00 $36.48▲ +7.29%▲ +7.29%$37.73 (+10.97%)
Aug 4, 2026
11w ago
Insider Cluster
NEUTRAL ★ 2/10
$35.00 $34.50▼ −1.43%▼ −0.83%$37.73 (+7.80%)
Jul 17, 2026
14w ago
Insider Cluster
NEUTRAL ★ 2/10
$30.62 $34.28▲ +11.95%▲ +7.50%$37.73 (+23.22%)
Showing 10 of 28

US Market Status

Market Closed — Opens Tue (17h 30m)

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Report published May 19, 2026