NEW YORK, Jan 9, 2026, 15:07 EST — Regular session
Twilio shares fell on Friday after a regulatory filing showed Chief Executive Khozema Shipchandler sold stock under a pre-arranged trading plan. The stock was down 3.9% at $132.13, after earlier trading as high as $138.39.
The disclosure matters now because Twilio has become a crowded, rate-sensitive software trade again, and investors are quick to react to any signal around insider activity. With the next earnings report weeks away, traders are trying to separate routine selling from a shift in tone ahead of 2026 guidance.
The broader market was firmer after a U.S. jobs report pointed to a slower pace of hiring, keeping attention on where interest rates go next. “Until the data provide a clearer direction, a divided Fed is likely to stay that way,” Morgan Stanley Wealth Management chief economic strategist Ellen Zentner said. 1
A Form 4 — the SEC’s insider-trading disclosure — showed Shipchandler sold 13,336 shares on Jan. 6 in three transactions, with prices ranging from $132.82 to $134.85 per share. The filing said the sales were made under a Rule 10b5-1 plan, which sets a preset schedule for trades, and listed 193,781 shares owned directly after the transactions. 2
A separate Form 4 signed on Jan. 7 showed Chief Financial Officer Aidan Viggiano sold 7,213 shares on Jan. 5 at $135.97 per share, also under a 10b5-1 plan. The filing showed 112,236 shares owned directly after the sale and said some of the holding consists of restricted stock units, or RSUs, which convert into shares when they vest.
Analysts have stayed busy on the name. Rosenblatt analyst Catharine Trebnick maintained a buy rating and raised her price target to $180 from $140 on Wednesday, according to a report carried by Benzinga. 3
Twilio sells communications tools that let developers add text, voice and other real-time messaging features to apps, and it also runs a customer-data platform business under the Segment brand. 4
But insider selling is often routine — especially when it runs through 10b5-1 plans — and it can overlap with compensation and tax timing rather than any change in the business. The bigger downside risk is that Twilio’s next outlook fails to back up the valuation investors have been willing to pay for improving growth and cash flow.
Next up is the earnings print and early 2026 guidance: earnings calendars vary, but TipRanks lists Twilio’s next report for Feb. 18 after the close. Investors will be looking for any change in demand for communications APIs and how much cash the company can generate as it scales.
