TWILIO INC (TWLO) · Insider Trading (Form 4) SEC Filing

=== SEC Form 4 — Statement of Changes in Beneficial Ownership === Document Type: 4 Period of Report: 2026-05-26 10b5-1 Pre-arranged Plan: Yes --- Issuer --- Name: TWILIO INC (TWLO) CIK: 0001447669 --- Reporting Owner --- Name: Shipchandler Khozema CIK: 0001737610 Role: Director, Officer (Chief Executive Officer) --- Non-Derivative Transactions --- [Transaction #1] Security: Class A Common Stock Date: 2026-05-26 | Code: M (Exercise of derivative) Shares: +32,158 | Price: $76.63 Total Value: $2,464,267.54 Shares Owned After: 267,700 | Ownership: D (Direct) Footnotes: [F1] The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #2] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -927 | Price: $180.70 Total Value: $167,510.57 Shares Owned After: 266,773 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F4] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $180.36 to $181.31 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #3] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -2,084 | Price: $181.96 Total Value: $379,205.89 Shares Owned After: 264,689 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F5] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $181.46 to $182.455 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #4] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -2,677 | Price: $182.75 Total Value: $489,234.06 Shares Owned After: 262,012 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F6] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $182.465 to $183.40 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #5] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -3,986 | Price: $184.55 Total Value: $735,621.88 Shares Owned After: 258,026 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F7] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $183.81 to $184.805 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #6] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -4,524 | Price: $185.15 Total Value: $837,619.50 Shares Owned After: 253,502 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F8] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $184.815 to $185.80 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #7] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -4,719 | Price: $186.55 Total Value: $880,317.65 Shares Owned After: 248,783 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F9] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $185.94 to $186.925 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #8] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -8,772 | Price: $187.19 Total Value: $1,642,006.12 Shares Owned After: 240,011 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F10] The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $186.94 to $187.62 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. [Transaction #9] Security: Class A Common Stock Date: 2026-05-26 | Code: S (Open market sale) Shares: -4,469 | Price: $188.00 Total Value: $840,172.00 Shares Owned After: 235,542 | Ownership: D (Direct) Footnotes: [F3] The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F2] A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. --- Derivative Transactions --- [Transaction #1] Security: Employee Stock Option (right to buy) Date: 2026-05-26 | Code: M (Exercise of derivative) Shares: -32,158 | Price: $0.00 Exercisable: N/A | Expires: 2028-10-31 Shares Owned After: 3,260 | Ownership: D (Direct) Footnotes: [F1] The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. [F11] The shares underlying the option are fully vested and exercisable. --- Footnotes (Complete Index) --- F1: The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. F10: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $186.94 to $187.62 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. F11: The shares underlying the option are fully vested and exercisable. F2: A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. F3: The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. F4: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $180.36 to $181.31 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. F5: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $181.46 to $182.455 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. F6: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $182.465 to $183.40 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. F7: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $183.81 to $184.805 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. F8: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $184.815 to $185.80 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. F9: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $185.94 to $186.925 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote. --- Signature --- /s/ /s/ Juliana Chen as attorney-in-fact for Reporting Person (2026-05-28)