TWLO TWILIO INC
Price Chart
Executive Summary
Three Twilio insiders sold a total of $184.71M in shares over a one-week window, with Director Andrew Stafman accounting for $184.14M (99.7% of the total). The CEO and another director made small sales ($168K and $398K, respectively). The massive Stafman sale represents ~0.53% of Twilio's $34.8B market cap, a notable but not alarming proportion. No insider buying occurred, and the cluster is overwhelmingly sell-side, though the CEO's sale is trivial in size.
Key Financial Metrics
Actionable Insight
The massive Stafman sale warrants attention — a director selling $184M in a single day is unusual and may signal a lack of confidence or portfolio rebalancing. However, the CEO's tiny sale and the absence of any insider buying suggest no uniform bearish view. Monitor for any subsequent Form 4 filings or corporate announcements (e.g., earnings, M&A) that could explain the timing. The stock's strong recent performance (historical reports show large positive T+20 moves) may have provided a selling opportunity.
Key Facts
- Director Andrew Stafman sold 1.00M shares for $184.14M on 2026-05-27, representing 99.7% of the cluster's total value.
- CEO Khozema Shipchandler sold 927 shares for $168K on 2026-05-26 — a de minimis amount.
- Director Erika Rottenberg sold 2,000 shares for $398K on 2026-06-01.
- Total insider selling of $184.71M equals ~0.53% of Twilio's $34.8B market cap.
- No insider purchases were reported in the cluster window.
- Recent 30-day insider activity shows 6 sells totaling $315.8M, indicating sustained selling pressure.
Financial Impact
Total insider selling of $184.71M, or ~0.53% of market cap, concentrated in a single director's sale.
Risk Factors
- Director Stafman's $184M sale could be interpreted as a negative signal by the market, especially given the concentrated nature.
- Sustained insider selling over 30 days ($315.8M total) may weigh on sentiment.
- No insider buying to offset the selling creates an asymmetric signal.
Market Snapshot
Documents Analyzed
This report is based on 1 SEC document filed with EDGAR.
| Document | Accession Number |
|---|---|
| CLUSTER Data (Synthetic) | cluster-TWLO-1780518276193 |
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Filters
| Type | Now | ||||
|---|---|---|---|---|---|
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Jun 11, 2026
5d ago
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Institutional Cluster
| $206.62 $204.08 | ▼ −1.23% | ▼ −1.77% | $192.68 (−6.75%) |
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Jun 3, 2026
13d ago
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Insider Cluster
| $235.39 $225.03 | ▲ +4.40% | ▲ +1.80% | $192.68 (+18.15%) |
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Jun 1, 2026
15d ago
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144
| $228.41 $226.89 | ▼ −0.67% | ▲ +0.06% | $192.68 (−15.64%) |
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May 21, 2026
26d ago
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Insider Cluster
| $187.86 $189.54 | ▼ −0.89% | ▼ −0.31% | $192.68 (−2.56%) |
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May 19, 2026
28d ago
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Insider Cluster
| $189.31 $182.52 | ▼ −3.59% | ▼ −3.78% | $192.68 (+1.78%) |
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May 4, 2026
6w ago
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144
| $194.54 $190.85 | ▼ −1.90% | ▼ −3.28% | $192.68 (−0.96%) |
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Apr 28, 2026
7w ago
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DEFA14A
| $140.09 $147.90 | ▲ +5.57% | ▲ +4.55% | $192.68 (+37.54%) |
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Apr 2, 2026
10w ago
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Insider Cluster
| $130.88 $131.00 | ▼ −0.09% | ▲ +0.38% | $192.68 (−47.22%) |
US Market Status
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