DBX DROPBOX, INC.

NEUTRAL Impact: 2/10 Insider Cluster (3 insiders)
Horizon days Filed May 19, 2026 Processed 24d 15h ago
Insider cluster: 2 insiders, $1.0M total
Latest settled — T+5d ⚠ clustered
DBX ▼ -4.87% at T+5d
NEUTRAL call ✗ call lost -4.87% · α vs SPY -6.67% · entry $27.53 → $26.19
Next anchor: T+20d in 4d
Currently $27.09 · -1.59% from $27.53 entry
Entry anchored
May 19, 2026
via day open
T+1d
-1.34%
call -1.34% · α -1.54%
$27.16
settled 24d ago
T+5d
-4.87%
call -4.87% · α -6.67%
$26.19
settled 17d ago
T+20d
call — · α —
in 4d
T+60d
call — · α —
in 2mo

Price Chart

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Executive Summary

Dropbox's CEO Andrew Houston sold ~$974K in open-market shares on 2026-05-14 following the conversion of derivates, and CTO Ali Dasdan sold ~$74K on 2026-05-18. The total open-market sales of ~$1.05M represent just 0.016% of the $6.5B market cap — well below the 0.1% materiality threshold. The CEO sale follows the company's Q1 earnings release (revenue +0.8%, GAAP net income -24%) and appears liquidity-driven (post-vesting sale).

Key Financial Metrics

Direction
selling
Total Value
$1.1M
Insiders
3

Actionable Insight

The CEO sale is routine in size and timing — follows a derivative conversion and is below the 0.025% of shares outstanding. No bearish read-through warranted. Monitor the next 10-Q for any acceleration in paying-user declines (18.09M vs 18.26M prior). Despite the weak historical calibration (-6.18% T+20 avg loss), this cluster itself lacks conviction for a position.

Key Facts

  • CEO Andrew Houston sold 37,498 shares at $25.96 on 2026-05-14, proceeds ~$974K
  • CTO Ali Dasdan sold 2,700 shares at $27.28 on 2026-05-18, proceeds ~$74K
  • Total open-market sales: ~$1.05M, or 0.016% of $6.5B market cap
  • Tax-withholding transactions (CTO ~$504K, CAO ~$96K) are non-cash and not informative
  • CEO sale immediately followed derivative conversion at $0 strike — pattern consistent with post-vesting liquidity
  • Q1 2026 earnings (May 7) showed revenue +0.8% YoY to $629.5M but GAAP net income fell 24% to $114.5M

Financial Impact

Open-market insider selling totals $1.05M, which is 0.016% of market cap — immaterial relative to $6.5B enterprise value

insider selling volumemarket sentiment

Risk Factors

  • CEO may continue selling in future windows, adding supply overhang
  • Paying user base declining sequentially (18.09M) could pressure subscription revenue growth
  • GAAP net income down 24% on higher interest expense from debt-funded buybacks

Market Snapshot

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

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-DBX-1779225427190
17 reports for DBX
Performance horizon
100% Hit rate 3 of 3 directional calls best @ T+5▲ +4.87%May 19, 2026
Filters
Rows
Reports for DBX — sortable, filterable
Type Now
Jun 3, 2026
9d ago
Insider Cluster
NEUTRAL ★ 3/10
$27.18 $27.38▲ +0.75%▲ +3.35%$27.09 (−0.31%)
Jun 1, 2026
11d ago
8-K
NEUTRAL ★ 4/10
$28.92 $28.16▼ −2.63%▼ −2.77%$27.09 (−6.32%)
May 26, 2026
17d ago
8-K
NEUTRAL ★ 4/10
$26.46 $25.97▼ −1.85%▼ −1.87%$27.09 (+2.38%)
May 20, 2026
23d ago
Insider Cluster
NEUTRAL ★ 3/10
$27.16 $27.51▲ +1.29%▲ +0.84%$27.09 (−0.25%)
May 20, 2026
23d ago
Insider Cluster
NEUTRAL ★ 2/10
$27.16 $27.51▲ +1.29%▲ +0.84%$27.09 (−0.25%)
May 20, 2026
23d ago
Insider Cluster
NEUTRAL ★ 2/10
$25.97 $26.19▲ +0.84%▲ +0.29%$27.09 (+4.32%)
May 20, 2026
23d ago
Insider Cluster
BEARISH ★ 4/10
$27.16 $27.51▼ −1.29%▼ −0.84%$27.09 (+0.25%)
May 20, 2026
23d ago
Insider Cluster
BEARISH ★ 5/10
$27.16 $27.51▼ −1.29%▼ −0.84%$27.09 (+0.25%)
May 19, 2026
24d ago
Insider Cluster
NEUTRAL ★ 4/10
$27.53 $27.16▼ −1.34%▼ −1.54%$27.09 (−1.59%)
May 19, 2026
24d ago
Insider Cluster
BEARISH ★ 5/10
$27.53 $27.16▲ +1.34%▲ +1.54%$27.09 (+1.59%)
Showing 10 of 17

US Market Status

Market Closed — Opens Mon (49h 3m)

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