Insider Cluster (2 insiders) ·Filed May 21, 2026

TWLO

TWILIO INC
BEARISH
Impact 4/10
Horizonweeks Processed4mo ago
Insider cluster: 2 insiders, $131.0M total
Actionable Insight ▼ Bearish

Monitor for further insider selling, especially from C-suite. The selling may be liquidity-driven, but a continued pattern could signal caution. Next earnings release will provide fundamental context.

DirectionBearish
Confidencemedium
Horizonweeks
Final — all horizons settled through T+60d
TWLO ▲ +22.90% at T+60d
SHORT call ✗ call lost -22.90% · α vs SPY -19.97% · entry $187.86 → $230.88
Entry anchored
May 21, 2026
via day open
T+1d
+0.89%
call -0.89% · α -0.31%
$189.54
settled 4mo ago
T+5d
+21.06%
call -21.06% · α -19.40%
$227.43
settled 4mo ago
T+20d
-2.25%
call +2.25% · α +2.08%
$183.64
settled 3mo ago
T+60d
+22.90%
call -22.90% · α -19.97%
$230.88
settled 6w ago

Price Chart

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Executive Summary

Two insiders at Twilio sold a combined $131M in shares over a week, led by Director Stafman's $130.6M sale. CFO Viggiano sold a small amount. While insider selling is often a negative signal, the total is modest relative to Twilio's $28.7B market cap, and director sales can be liquidity-driven. The cluster does not suggest a material deterioration in business fundamentals.

Key Financial Metrics

Direction
selling
Total Value
$131.0M
Insiders
2

Key Facts

  • Director Stafman sold 675,000 shares for $130.64M on 2026-05-12.
  • CFO Viggiano sold 1,828 shares for $365,600 on 2026-05-19.
  • Total insider sales in the cluster: ~$131M, representing ~0.46% of market cap.
  • Selling occurred within a 7-day window.

Financial Impact

Insider selling of $131M, ~0.46% of market cap

insider confidence

Risk Factors

  • Further insider selling could pressure stock sentiment.
  • Director's large sale may indicate concerns about valuation or growth outlook.

Market Snapshot

Exchange
NYSE
Sector
Services-Prepackaged Software
Analyst Consensus
81% bullish (36 analysts)

Investment Themes

Software & IT

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-TWLO-1779394959878
14 reports for TWLO
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for TWLO — sortable, filterable
TypeNow
Aug 19, 2026
6w ago
Insider Cluster
NEUTRAL ★ 4/10
$221.87 $246.24▲ +10.98%▲ +12.94%$294.86 (+32.90%)
Aug 10, 2026
7w ago
144
NEUTRAL ★ 2/10
$255.95 $227.19▼ −11.24%▼ −10.18%$294.86 (+15.20%)
Jul 8, 2026
12w ago
Insider Cluster
NEUTRAL ★ 2/10
$215.50 $193.22▼ −10.34%▼ −13.61%$294.86 (+36.82%)
Jul 7, 2026
12w ago
Insider Cluster
NEUTRAL ★ 2/10
$211.97 $196.59▼ −7.26%▼ −8.59%$294.86 (+39.10%)
Jul 2, 2026
13w ago
Insider Cluster
NEUTRAL ★ 2/10
$209.31 $190.94▼ −8.78%▼ −8.36%$294.86 (+40.87%)
Jun 17, 2026
15w ago
8-K
NEUTRAL ★ 2/10
$186.17 $206.70▲ +11.03%▲ +10.49%$294.86 (+58.38%)
Jun 11, 2026
16w ago
Institutional Cluster
NEUTRAL ★ 3/10
$206.62 $218.60▲ +5.80%▲ +3.91%$294.86 (+42.70%)
Jun 3, 2026
17w ago
Insider Cluster
BEARISH ★ 5/10
$235.39 $209.31▲ +11.08%▲ +9.45%$294.86 (−25.26%)
Jun 1, 2026
17w ago
144
NEUTRAL ★ 2/10
$228.41 $209.28▼ −8.38%▼ −6.56%$294.86 (+29.09%)
May 21, 2026
19w ago
Insider Cluster
BEARISH ★ 4/10
$187.86 $183.64▲ +2.25%▲ +2.08%$294.86 (−56.95%)
Showing 10 of 14

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Report published May 21, 2026