Twilio Stock Insider Power

Based on the 100 latest insides trades, we have calculated the insider power to be negative at -98.24. In total, the insiders bought 193.88K and sold 2.9M TWLO shares in the last 100 trades. The insider score can be negative despite buy/sell ratio being positive. The score focuses on the quality of the trades.

Insider Power

(Last 100 transactions)
-98.24
Buy 193.88K shares
Sell 2.9M shares
32% Buy Activity
Negligible or No Correlation
Sell Signal Medium Confidence
May 27, 2026

Analysis Breakdown:

  • Strongly supported by a very low Insider Power Score of -98.24.
  • Confidence increased due to high data reliability score of 100.

Historical Insider Trades

Date Type Person Role Amount
May 27, 2026
Sell
Class A Common Stock
S-Sale
Stafman Andrew
Director
Director 1 000 000
Value: $0.18B
May 26, 2026
Buy
Employee Stock Option (right to buy)
M-Exempt
Shipchandler Khozema
Chief Executive Officer
CEO / President 32 158
Value: $2.46M
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 4 469
Value: $840.2K
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 8 772
Value: $1.64M
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 4 719
Value: $880.3K
May 26, 2026
Buy
Class A Common Stock
M-Exempt
Shipchandler Khozema
Chief Executive Officer
CEO / President 32 158
Value: $2.46M
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 927
Value: $167.5K
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 2 084
Value: $379.2K
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 2 677
Value: $489.2K
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 3 986
Value: $735.6K
May 26, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 4 524
Value: $837.6K
May 19, 2026
Sell
Class A Common Stock
S-Sale
Viggiano Aidan
Chief Financial Officer
C-Suite Officer 1 828
Value: $365.6K
May 15, 2026
Sell
Class A Common Stock
S-Sale
Viggiano Aidan
Chief Financial Officer
C-Suite Officer 476
Value: $93.7K
May 15, 2026
Sell
Class A Common Stock
S-Sale
Viggiano Aidan
Chief Financial Officer
C-Suite Officer 900
Value: $178.0K
May 12, 2026
Sell
Class A Common Stock
S-Sale
Stafman Andrew
Director
Director 675 000
Value: $0.13B
May 04, 2026
Sell
Class A Common Stock
S-Sale
Rottenberg Erika
Director
Director 1 500
Value: $278.0K
Apr 21, 2026
Sell
Class A Common Stock
S-Sale
Rottenberg Erika
Director
Director 215
Value: $32.1K
Apr 21, 2026
Sell
Class A Common Stock
S-Sale
Rottenberg Erika
Director
Director 1 585
Value: $236.2K
Apr 06, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 2 100
Value: $283.5K
Apr 06, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 2 800
Value: $369.4K
Apr 06, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 5 315
Value: $707.2K
Apr 06, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 5 500
Value: $736.1K
Apr 02, 2026
Sell
Class A Common Stock
S-Sale
Viggiano Aidan
Chief Financial Officer
C-Suite Officer 5 047
Value: $645.7K
Apr 02, 2026
Sell
Class A Common Stock
S-Sale
Viggiano Aidan
Chief Financial Officer
C-Suite Officer 4 342
Value: $551.5K
Mar 31, 2026
Sell
Class A Common Stock
S-Sale
Shipchandler Khozema
Chief Executive Officer
CEO / President 100
Value: $12.5K

About Insider Power

Insider Power is a proprietary algorithm developed by StockInvest.us to evaluate the significance of insider transactions. The calculation considers the size, type, and timing of transactions, as well as the insider’s role within the company.

It is important to note that, in general, there is little to no correlation between insider transactions and short-term stock price movements. In one of our studies, only 0.22%* of stocks with insider activity showed a measurable correlation — and even then, it was unclear whether the effect was caused by insider actions or simply by the stock’s broader trend.

While our algorithms are designed to highlight potentially meaningful signals, these cannot be regarded as statistically significant on their own. Insider trading activity should therefore be seen as informative rather than as direct trading guidance. The Insider Power metric was created to present this information in a clearer and more accessible way, helping investors better understand the possible context of insider activity.

* October 6th, 2025 - Tested on 5562 stocks

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ABOUT TWILIO INC
Twilio
Twilio Inc., together with its subsidiaries, provides a cloud communications platform that enables developers to build, scale, and operate customer engagement within software applications in the United States and internationally. Its customer engagement platform provides a set of application programming interfaces that handle the higher-level communication logic needed for nearly every type of customer engagement, as well as enable developers to ...
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