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Insider Cluster (5 insiders) ·Filed Sep 15, 2026

DBX

DROPBOX, INC.
BEARISH
Impact 5/10
Horizondays Processed1mo ago
Insider cluster: 5 insiders, $16.4M total
Actionable Insight ▼ Bearish

The cluster of C-suite selling (both Co-CEOs and CFO) within a 2-day window is a bearish signal, though the dollar amount is modest relative to market cap. Monitor for any upcoming 8-K filings (earnings, guidance, or material agreements) that could explain the timing. Consider hedging long positions or reducing exposure until the next catalyst.

DirectionBearish
Confidencemedium
Horizondays
Latest settled — T+20d
DBX ▼ -5.62% at T+20d
SHORT call ✓ call won +5.62% · α vs SPY +7.68% · entry $37.74 → $35.62
Next anchor: T+60d in 6w
Latest observation: T+27 +15.24% FF3 residual α
Entry = T+0 close
Sep 15, 2026
via day close
T+1d
-0.34%
call +0.34% · α +1.48%
$37.61
settled 6w ago
T+5d
-9.33%
call +9.33% · α +11.89%
$34.22
settled 5w ago
T+20d
-5.62%
call +5.62% · α +7.68%
$35.62
settled 13d ago
T+60d
Pending
in 6w

Price Chart

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Executive Summary

A cluster of insider selling at Dropbox (DBX) totaling $16.38M over a 7-day window, led by Co-CEO Andrew Houston ($13.44M) and CFO Ross Tennenbaum ($3.42M). The selling is concentrated in open-market sales by top C-suite executives, which is notable given the $8.4B market cap (0.2% of market cap). While insider sales are generally less predictive than buys, the involvement of both Co-CEOs and the CFO in a tight cluster warrants attention, especially with the company's mixed analyst consensus (6% bullish) and recent institutional trimming.

Key Financial Metrics

Direction
selling
Total Value
$16.4M
Insiders
5

Key Facts

  • Total insider selling of $16.38M over 7 days, representing ~0.2% of $8.4B market cap
  • Co-CEO Andrew Houston sold $13.44M (324,432 + 59,368 shares) on 2026-09-10
  • CFO Ross Tennenbaum sold $3.42M (97,558 shares) on 2026-09-10
  • Co-CEO Ashraf Alkarmi sold $1.02M (28,800 shares) on 2026-09-11
  • Co-CEO Houston also converted 383,800 derivative shares at $0 (non-cash) on 2026-09-10
  • Director Lisa Campbell sold $160K and CLO William Yoon sold $431K on 2026-09-04
  • Analyst consensus is 6% bullish (0 Strong Buy, 1 Buy, 7 Hold, 7 Sell, 1 Strong Sell)
  • Institutional 13F shows 7 trims and 5 doubled positions in Q2 2026

Financial Impact

$16.38M in open-market sales by insiders, ~0.2% of market cap

insider ownershipmarket sentiment

Risk Factors

  • Insider sales may be liquidity-driven (10b5-1 plans, diversification) rather than informational
  • The $16.38M is only 0.2% of market cap, below the 0.5% threshold for 'significant' impact
  • Co-CEO Houston's derivative conversion (non-cash) suggests some sales may be for tax or plan purposes

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-1789511786442
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
5d 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
21d 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
6w 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 (< 1m)

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Report published Sep 15, 2026