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Insider Cluster (4 insiders) ·Filed Oct 19, 2026

DBX

DROPBOX, INC.
BEARISH
Impact 4/10
Horizonweeks Processed7d 19h ago
Insider cluster: 4 insiders, $15.9M total
Actionable Insight ▼ Bearish

Cluster of unplanned open-market sales by top executives (both Co-CEOs and CFO) is unusual and suggests insiders see limited near-term upside. Monitor next 10-Q for any guidance revision or operational weakness that could explain the selling.

DirectionBearish
Confidencemedium
Horizonweeks
Latest settled — T+5d
DBX ▲ +4.98% at T+5d
SHORT call ✗ call lost -4.98% · α vs SPY -5.13% · entry $35.94 → $37.73
Next anchor: T+20d in 20d
Entry = T+0 close
Oct 19, 2026
via day close
T+1d
+1.17%
call -1.17% · α -0.83%
$36.36
settled 7d ago
T+5d
+4.98%
call -4.98% · α -5.13%
$37.73
settled yesterday
T+20d
Pending
in 20d
T+60d
Pending
in 3mo

Price Chart

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Executive Summary

Four Dropbox insiders, including both Co-CEOs and the CFO, sold a combined $15.86M in open-market sales over a one-week window. The sales represent ~0.1% of market cap and are not plan-driven, signaling potential concern about valuation or near-term fundamentals.

Key Financial Metrics

Direction
selling
Total Value
$15.9M
Insiders
4

Key Facts

  • Total insider sales of $15.86M from 4 insiders (Co-CEOs, CFO, CAO) between Sep 8-15, 2026
  • Co-CEO Andrew Houston sold $11.35M (324.4K shares at $34.98)
  • CFO Ross Tennenbaum sold $3.42M (97.6K shares at $35.02)
  • Co-CEO Ashraf Alkarmi sold $1.02M (28.8K shares at $35.54)
  • CAO Sarah Schubach sold $74K (2.0K shares at $36.78)
  • No 10b5-1 plan indication on any trade — all open-market sales
  • Sales represent approximately 0.1% of Dropbox's market cap

Financial Impact

$15.86M in insider sales, ~0.1% of market cap

insider ownershipmarket sentiment

Risk Factors

  • Insider sales may be liquidity-driven despite no 10b5-1 plan, but cluster timing and seniority is atypical
  • No explicit negative catalyst cited in filing — selling may pre-date upcoming earnings or product news

Investment Themes

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DBX-1792438804343
28 reports for DBX
Performance horizon
100% Hit rate @ T+20 6 of 6 directional calls Went positive at some point 6 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—$37.08 (+1.07%)
Oct 19, 2026
7d ago
Insider Cluster
BEARISH ★ 4/10
$35.94awaiting T+20—$37.08 (−3.17%)
Oct 5, 2026
21d ago
Insider Cluster
NEUTRAL ★ 4/10
$33.73awaiting T+20—$37.08 (+9.93%)
Sep 17, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$36.48 $35.57▲ +2.49%▲ +2.70%$37.08 (−1.64%)
Sep 15, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$37.74 $35.62▲ +5.62%▲ +7.68%$37.08 (+1.75%)
Sep 14, 2026
6w ago
Insider Cluster
BEARISH ★ 5/10
$37.63 $35.60▲ +5.39%▲ +8.37%$37.08 (+1.46%)
Sep 9, 2026
6w ago
Insider Cluster
NEUTRAL ★ 2/10
$35.05 $34.14▼ −2.60%▼ −4.97%$37.08 (+5.79%)
Aug 19, 2026
9w ago
Insider Cluster
NEUTRAL ★ 4/10
$34.00 $36.48▲ +7.29%▲ +7.29%$37.08 (+9.06%)
Aug 4, 2026
11w ago
Insider Cluster
NEUTRAL ★ 2/10
$35.00 $34.50▼ −1.43%▼ −0.83%$37.08 (+5.94%)
Jul 17, 2026
14w ago
Insider Cluster
NEUTRAL ★ 2/10
$30.62 $34.28▲ +11.95%▲ +7.50%$37.08 (+21.10%)
Showing 10 of 28

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Report published Oct 19, 2026