TWLO Stock: Insider Activity, Filings & Research
Drillr aggregates AI research, SEC filings, earnings signals and alt-data for TWLO. 3 published articles.
Insider Activity
Over the trailing 90-day period, Twilio (TWLO) insiders engaged in significant net selling activity totaling $327.8M across 30 open-market sales transactions, with no offsetting purchases. Director Andrew Stafman accounted for the majority of activity, selling $184.1M on May 27 and $130.6M on May 12, while CEO and director Khozema Shipchandler sold $1.6M on May 28. The insider sentiment score of 0/100 reflects predominantly bearish positioning with no cluster buying observed. Despite the substantial insider selling, the stock delivered an 85.7% price return over the period, while the institutional 13F trend remained mixed.
Updated Jun 4, 2026 · based on SEC Form 4 filings · not investment advice
| Date | Insider | Type | Shares | Price |
|---|---|---|---|---|
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 4,719 | $186.55 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Option | 32,158 | $76.63 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 2,677 | $182.75 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 3,986 | $184.55 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 8,772 | $187.19 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 2,084 | $181.96 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 927 | $180.70 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 4,469 | $188.00 |
| May 28, 2026 | Shipchandler Khozemadirector, officer: Chief Executive Officer | Sell | 4,524 | $185.15 |
| May 27, 2026 | Stafman Andrewdirector | Sell | 1,000,000 | $184.14 |
| May 21, 2026 | Viggiano Aidanofficer: Chief Financial Officer | Sell | 1,828 | $200.00 |
| May 19, 2026 | Viggiano Aidanofficer: Chief Financial Officer | Sell | 476 | $196.76 |
| May 19, 2026 | Viggiano Aidanofficer: Chief Financial Officer | Sell | 900 | $197.80 |
| May 12, 2026 | Stafman Andrewdirector | Sell | 675,000 | $193.54 |
| May 6, 2026 | ROTTENBERG ERIKAdirector | Sell | 1,500 | $185.32 |
Source: TWLO SEC Form 4 filings, latest May 28, 2026. For informational purposes only — not investment advice.
Research
Which enterprise verticals are switching CCaaS vendors fastest — and does Five9 or NICE win those deals?
NICE dominates enterprise-wide CCaaS vendor switches — particularly in financial services — with 66% gross margins and 22% operating margins, while Five9 wins mid-market and BPO deals at faster growth rates but thinner margins. At 5.3x forward P/E, Five9 is a turnaround bet; NICE at 11x forward earnings is the quality compounder in a market where Amazon Connect looms as the disruptive low-cost entrant.
FIVNNICEAMZNDoes Twilio or Amazon Connect pose a bigger substitution threat to Five9 and NICE than each other?
Amazon Connect poses a greater substitution threat to Five9 and NICE than Twilio due to AWS's enterprise distribution advantage, AI infrastructure dominance, and disruptive per-minute pricing model. Five9 is more vulnerable than NICE given its narrower product suite and $33M operating income vs. NICE's $660M, leaving less room to invest defensively against platform giants.
AMZNFIVNNICEWho Wins the $500B Contact Center AI Disruption — NICE, Salesforce, or the New Entrants?
The $500B contact center market is undergoing structural disruption as AI agents replace human representatives at scale, creating a clear opportunity for cloud CCaaS and infrastructure providers. NICE and Salesforce lead the field with defensible AI platforms and strong profitability, while Five9 faces a binary outcome and Twilio offers durable infrastructure exposure across the broader AI agent ecosystem.
NICECRMFIVN
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