Insider Cluster (2 insiders) ·Filed May 19, 2026

TWLO

TWILIO INC
NEUTRAL
Impact 4/10
Horizondays Processed4mo ago
Insider cluster: 2 insiders, $130.7M total
Actionable Insight • Neutral

A director selling $130M is a notable wealth-transfer event but not unusual for a $30B company; the CFO's $94K sale is trivial. Without a material earnings miss or guidance cut context, this cluster alone does not signal impending bearish news — treat as routine portfolio rebalancing absent additional negative cross-filings. Watch for any 8-K earnings (2.02) or a late-filing (NT) within 30 days, as those combos are amplifiers per actuarial verdicts and would escalate bearish weight.

DirectionNeutral
Confidencemedium
Horizondays
Final — all horizons settled through T+60d
TWLO ▲ +24.85% at T+60d
NEUTRAL call ✓ call won +24.85% · α vs SPY +20.12% · entry $189.31 → $236.36
Entry anchored
May 19, 2026
via day open
T+1d
-3.59%
call -3.59% · α -3.78%
$182.52
settled 5mo ago
T+5d
-2.55%
call -2.55% · α -4.35%
$184.49
settled 4mo ago
T+20d
-0.64%
call -0.64% · α -0.60%
$188.11
settled 4mo ago
T+60d
+24.85%
call +24.85% · α +20.12%
$236.36
settled 7w ago

Price Chart

Loading chart...

Executive Summary

Two TWLO insiders — CFO Aidan Viggiano ($94K) and Director Andrew Stafman ($130.64M) — sold a combined $130.7M in open-market transactions over a 7-day window. Stafman's $130.6M sale alone represents ~0.44% of TWLO's $30B market cap, the fourth-largest insider sale at the company in 30 days, which is notable but not overwhelming relative to the company's size and typical insider liquidity events at a $30B software firm.

Key Financial Metrics

Direction
selling
Total Value
$130.7M
Insiders
2

Key Facts

  • Director Andrew Stafman sold 675,000 shares at ~$193.54 for total proceeds of $130.64M on 2026-05-12.
  • CFO Aidan Viggiano sold 476 shares at ~$196.76 for total proceeds of $93,660 on 2026-05-15.
  • Total cluster value: $130.73M in open-market sales, or ~0.44% of market cap.
  • Overall net direction is selling by an overwhelming $130.7M margin.
  • Stafman's sale is large in absolute terms but consistent with a $30B market cap company where director-level diversification sales are routine; CEO/CFO not joining the large sale reduces bearish signal.
  • The aggregate insider cluster + late-filing-context and + press-context are statistically AMPLIFIERS per cross-filing calibrations, but no late-filing or press context is provided here to activate those amplifications.

Financial Impact

$130.7M in insider open-market sales (0.44% of market cap)

dilutioninsider-sentiment

Risk Factors

  • Persistent insider selling by multiple C-suite or board members in future clusters would escalate risk.
  • No current earnings or guidance catalysts are bundled — this cluster's standalone signal is weak.
  • Stafman's sale is a single large director diversification event, not a pattern of informed selling.

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-1779222097625
14 reports for TWLO
Performance horizon
100% Hit rate 3 of 3 directional calls best @ T+5▲ +12.22%Jun 3, 2026
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

US Market Status

Market Open — Closes in 3h 40m

Subscribe to SecBot

Get Real-Time SEC Filing Intelligence

Comprehensive SEC filing analysis delivered the moment filings hit EDGAR. Sentiment scoring, impact analysis, and actionable insights for every material event.

Try SecBot Free Coming soon: SecBot Pro with alerts, watchlists, and API access
Report published May 19, 2026