SEC Form DEFA14A filed by Twilio Inc.

Twilio Proxy Statement Supplement May 2024 ©2024 TWILIO INC. ALL RIGHTS RESERVED

Twilio has taken extensive actions to position the company for future success Mar 5, 2024 Feb 13-15, 2023 Announced additional operational and financial actions: Mar 27, 2023 • Outcome of Segment review, with plan to reach BU Dec 4, 2023 Undertook comprehensive review of strategy and break-even non-GAAP operating profitability by Q2 2025 Announced sale of Sep 14, 2022 Strategic, operations to more effectively drive long-term • Accelerated consolidated GAAP operating profitability Announced additional IoT business sustainable growth, which resulted in: Operational & target to Q4 2025 Implemented actions to enhance profitable • New operating model for the business, including • Additional $2 billion share repurchase authorization corporate growth, including: Financial separation into two business units • Restructuring Segment restructuring • Streamlined go-to-market Actions business unit including 11% Jun 8, 2023 • Rationalized OpEx • Reducing workforce by workforce reduction Jan 8, 2024 • Reduced workforce by additional 17% Announced sale of additional 5% Initiated operational review of • Launched $1 billion share repurchase program ValueFirst business Segment business unit • Introduced GAAP profitability target of FY 2027 Aug-22Sep-22Oct-22Nov-22Dec-22Jan-23Feb-23Mar-23Apr-23May-23Jun-23Jul-23Aug-23Sep-23Oct-23Nov-23Dec-23Jan-24Feb-24Mar-24Apr-24May-24Jun-24 Timeline Mar 30, 2024 Jan 8, 2024 Board & Aug 4, 2022 Mar 28, 2023 Jun 6, 2024 Appointed Andy Announced: Jun 28, 2023 Corporate Stafman, a Appointed Miyuki Appointed Charlie • Appointment of Khozema Management proposal to Governance representative of a Suzuki as a new Bell as a new Sunset dual-class Shipchandler as new CEO declassify the Board to be major Twilio independent independent share structure • Separation of Chair and CEO roles Actions voted on at AGM shareholder, as a new director director • Appointment of an independent independent director Board chair ©2024 TWILIO INC. ALL RIGHTS RESERVED 2

Our actions have materially improved key financial metrics; we’re targeting GAAP operating profitability by Q4 2025 (1) 2021 LTM Primary Focus Durable Growth Strategy on Rapid Growth Profitable Growth GAAP Operating Loss ($916M) ($656M) Non-GAAP Operating Profit $3M $589M Net Cash Provided by Operating Activities ($58M) $703M Free Cash Flow ($148M) $655M (2) Headcount 7.9K 5.6K Stock-Based Compensation / Revenue 22% 16% (3) $0 $931M Share Repurchases Prior to 2023 $3B authorized for 2023-2024 (1) LTM figures as of March 31, 2024. (2) 2021 headcount figure as of December 31, 2021. LTM headcount figure as of March 31, 2024. (3) The Board authorized $1 billion of share repurchases in February 2023, and a further $2 billion of share repurchases in March 2024. We’re targeting to complete the full $3 billion of repurchases by the end of this year. ©2024 TWILIO INC. ALL RIGHTS RESERVED Note: Non-GAAP operating profit (also referred to as non-GAAP income from operations) and free cash flow are non-GAAP financial measures. Refer to Non-GAAP Financial Measures in the appendix for their definitions and a 3 reconciliation of each non-GAAP measure to its most directly comparable GAAP measure.

Extensive stockholder engagement informed significant changes to our executive compensation program Stockholder Engagement Resulting Executive Compensation Changes Stockholder Feedback Responsive Action Taken by Twilio ● In 2023, we enhanced our stockholder engagement program by shifting to a • Reduced salary of former CEO and did not increase base Improve alignment salaries of our NEOs for either 2023 or 2024, except in bi-annual outreach in the spring and fall between pay and connection with promotions performance ● Specifically, we conducted extensive outreach to our stockholders to better • Updated peer group for 2023 and 2024 compensation programs, resulting in a reduction in our market understand their perspectives with respect to our executive compensation compensation benchmarks practices • Transitioned from one-year performance periods for PSUs Incorporate longer awarded in 2022 to a three-year cumulative performance performance periods period for PSUs awarded going forward ● We responded to the feedback gathered by making significant changes to our for PSU awards • Compensation Committee selected non-GAAP income from executive compensation program, aligning incentive programs with the Incorporate operations as the performance target metric for the profitability metrics in preferences of our stockholders performance-based cash awards granted in 2023 compensation program • PSUs granted in 2024 will vest based on the achievement of (i) three-year cumulative free cash flow targets (70% weighting) and (ii) our relative TSR measured against the S&P 500 over a three-year period (30% weighting) • Implemented an annual cash bonus plan for executives Adopt a short-term beginning in 2024 incentive plan • Each NEO will have an annual cash bonus opportunity, with 57% 46% 100% payouts tied to the achievement of (i) organic revenue growth targets (50% weighting) and (ii) non-GAAP income from operations targets (50% weighting) • Maximum payout opportunities will be capped at 150% of We reached out to 21 We conducted meetings Independent directors base salary institutional investors with 14 institutional participated in 100% of holding approximately investors holding meetings with • 2023 served as a transition year to an annual cash bonus 57% of our shares approximately 46% of our institutional investors plan; we granted performance-based cash awards in 2023 outstanding shares outstanding based on the achievement of performance targets for annual non-GAAP income from operations ©2024 TWILIO INC. ALL RIGHTS RESERVED 4

Twilio’s executive compensation is centered on performance-based equity Our compensation program incorporates stockholder feedback and aligns executive outcomes with stockholder experience Note: Jeff Lawson, our co-founder, served as our CEO during 2023. Mr. Lawson stepped down as CEO on January 8, 2024. ©2024 TWILIO INC. ALL RIGHTS RESERVED 5

Compensation program outcomes are aligned with stockholders ● Our 2022 PSUs are subject to rigorous performance targets, and require robust performance for executives to receive any payout; no additional PSUs were awarded in 2023. ● In response to stockholder feedback, the Compensation Committee has approved 3-year performance periods for future PSU awards 2022 PSU Grant - Performance Measures PSU Payout as % Result Tranche of Target Threshold Target Maximum (payout at 50%) (payout at 100%) (payout at 200%) (1) 2022 Organic Revenue Growth 20% 30% 40% 29.7% 98.5% (1) Organic Revenue Growth 20% 30% 40% 10% 0% AND based on FY’23 2023 organic revenue Non-GAAP Income from (2) (2) growth results Profitable Profitable (1) Operations Projected: 7% (1) Organic Revenue Growth 20% 30% 40% 0% (through Q1’24) AND 2024 based on organic (2) revenue growth Non-GAAP Income from Profitable (2) Profitable results through (1) (through Q1’24) Operations Q1 2024 The 2023 tranche of our 2022 PSUs was not paid out, and based on organic revenue growth results through Q1 2024, the 2024 tranche of our 2022 PSUs is unlikely to be paid out (1) Organic revenue growth and non-GAAP income from operations are non-GAAP financial measures. Refer to “Non-GAAP Financial Measures” in the appendix for their definitions and a reconciliation of each non-GAAP measure to its most directly comparable GAAP measure. ©2024 TWILIO INC. ALL RIGHTS RESERVED (2) Profitability is defined as ≥$1.00 non-GAAP income from operations. 6

Twilio’s Board has taken a thoughtful approach to refreshment The skills, qualities, attributes, experience and diversity of our directors provide us with the broad range of perspectives to effectively oversee our evolving business needs and represent the best interests of our stockholders # of (1) Skills / Experiences Link to Strategy and Oversight Independence Tenure Directors Technology and Software Deep insight in the technology and software industries to oversee 8 Industry our business and the risks we face related to those industries. Deep insight in the communications industry to oversee our Communications Industry 3 business and the risks associated with these sectors. Experience to understand the dynamics and operation of a public Public Company Board 8 89% ~2.5 company. Independent Years Experience in senior leadership positions at a public company to Public Company Executive / (Avg.) 8 analyze, advise and oversee management in decision making, Senior Leadership operations and policies. Knowledge of financial markets, financing and accounting and Finance / Accounting / Audit 9 financial reporting processes to ensure proper oversight. Sales and marketing experience to provide expertise and guidance Sales and Marketing 3 to grow sales and enhance our brand. Human Capital / Experience attracting and retaining top talent to advise and Compensation / Employee 7 oversee our people and compensation policies in our competitive (2) Gender Diversity Racial/Ethnic Diversity Development and Training environment. Experience and knowledge of global operations, business Global Business Operations 8 conditions and culture to advise and oversee our global business. Risk Management 6 Expertise to oversee risk management. Regulatory / Government / Expertise to provide guidance and oversight of governmental and 33% 5 Public Policy regulatory affairs. 33% Racially/ Female Cybersecurity / Information Expertise to oversee cybersecurity, information security, and Ethnically 4 Security / Privacy privacy management. Diverse Strategy / Business Experience creating long-term value through investment, 9 Development / M&A acquisitions and growth strategies. Experience in corporate governance, compliance, policy, investor Corporate Governance 8 relations and creating long term sustainable value. (1) We have added four new independent directors since the beginning of 2021. ©2024 TWILIO INC. ALL RIGHTS RESERVED (2) Includes directors who identify in any of the following categories: African American or Black, Hispanic or Latinx, Asian, Native American or Alaskan Native, Native Hawaiian or Other Pacific Islander, or North African or Middle Eastern. 7 Note: Each of the graphics above excludes Byron Deeter, who is not standing for re-election at the Annual Meeting.

Twilio has a highly qualified, engaged and independent board Our Board proactively evaluates its composition in the context of Twilio’s evolving business to ensure our directors have backgrounds that collectively add value to strategic decisions and enable rigorous oversight of management Charles Bell Donna Dubinsky Jeff Epstein – Independent Chair •EVP, Security, Compliance, Identity and •Former CEO and Chair, Numenta •Operating Partner, Bessemer Venture Partners Management, Microsoft •Director since 2018 •Director since 2017 •Director since 2023 •Expertise in business strategy, innovation, •In-depth knowledge of accounting, finance, •Deep understanding of technology industry executive leadership growth and the operations, risk management and and significant cybersecurity expertise technology landscape technology Jeff Immelt Deval Patrick Erika Rottenberg •Partner, New Enterprise Associates •Former Governor of Massachusetts •Former GC, LinkedIn •Former CEO and Chairman, GE •Director since 2021 •Director since 2016 •Director since 2019 •Expertise in leadership, public policy, •Expertise in corporate governance, business investment and the economy operations, risk management, data •Expertise in global business, financing protection and regulatory matters strategy, operations, sales and marketing and human capital management Khozema Shipchandler - CEO Andrew Stafman Miyuki Suzuki •Chief Executive Officer, Twilio •Partner, Sachem Head Capital Management •Former President, Asia Pacific, Japan and China, Cisco •Director since 2024 •Former Associate, Silver Lake Partners •Director since 2022 •Significant operational and financial •Director since 2024 •Experience with multinational companies, leadership skills and expertise, as well as a •Shareholder representative with extensive deep and valuable understanding of Twilio’s telecom and networking industries, knowledge of corporate strategy, finance business, operations and culture operations and the regulatory environment and governance matters ©2024 TWILIO INC. ALL RIGHTS RESERVED Independent Director Added Since Beginning of 2021 8

We ask for your support at the 2024 annual meeting Proposal Recommendation Election of Jeff Epstein, Khozema Shipchandler and Andrew Stafman as Item 1 FOR Class II Directors Ratification of the appointment of KPMG LLP as the Company’s independent Item 2 FOR registered public accounting firm for the fiscal year ending December 31, 2024 Approval, on a non-binding advisory basis, of the compensation of the Item 3 FOR Company’s named executive officers Approval, on a non-binding advisory basis, of the preferred frequency of future Item 4 ONE YEAR non-binding advisory votes on the compensation of named executive officers Proposal to amend the certificate of incorporation to declassify the Item 5 FOR board of directors ©2024 TWILIO INC. ALL RIGHTS RESERVED 9

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Appendix ©2024 TWILIO INC. ALL RIGHTS RESERVED

Forward-Looking Statements This presentation contains forward-looking statements within the meaning of the federal securities laws, which statements involve substantial risks and uncertainties. Forward-looking statements generally relate to future events or our future financial or operating performance. In some cases, you can identify forward-looking statements because they contain words such as “may,” “can,” “will,” “would,” “should,” “expects,” “plans,” “anticipates,” “could,” “intends,” “target,” “projects,” “contemplates,” “believes,” “estimates,” “predicts,” “forecasts,” “potential” or “continue” or the negative of these words or other similar terms or expressions that concern our expectations, strategy, plans or intentions. Forward-looking statements contained in this presentation include, but are not limited to, statements about: our future financial performance, including our expected financial results and our guidance; our expectations regarding profitability, including when we will become profitable on GAAP and non-GAAP bases; our anticipated strategies and business plans; our ability to execute on our announced plans and targets for Segment following our operational review; our expectations regarding compensation programs, including PSU tranche payouts; our expectations regarding levels of stock-based compensation; the reorganization of our business and the shift in our segment reporting structure; and our expectations regarding share repurchases. You should not rely upon forward-looking statements as predictions of future events. The outcome of the events described in these forward-looking statements is subject to known and unknown risks, uncertainties, and other factors that may cause our actual results, performance, or achievements to differ materially from those described in the forward-looking statements, including, among other things: our ability to successfully implement our cost-saving initiatives and to capture expected efficiencies; our ability to realize the anticipated benefits of changes to our operating model and organizational structure; the impact of macroeconomic uncertainties and market volatility; our financial performance, including expectations regarding our results of operations and the assumptions underlying such expectations, and ability to achieve and sustain profitability; our ability to attract and retain customers; our ability to compete effectively in an intensely competitive market; our ability to comply with modified or new industry standards, laws and regulations applying to our business, and increased costs associated with regulatory compliance; our ability to manage changes in network service provider fees and optimize our network service provider coverage and connectivity; our ability to form and expand partnerships; and our ability to successfully enter into new markets and manage our international expansion. The forward-looking statements contained in this presentation are also subject to additional risks, uncertainties, and factors, including those more fully described in our most recent filings with the Securities and Exchange Commission, including our Annual Report on Form 10-K and subsequent Quarterly Reports on Form 10-Q. Should any of these risks materialize, or should our assumptions prove to be incorrect, actual financial results could differ materially from our projections or those implied by these forward-looking statements. Further information on potential risks that could affect actual results will be included in the subsequent periodic and current reports and other filings that we make with the Securities and Exchange Commission from time to time. Moreover, we operate in a very competitive and rapidly changing environment, and new risks and uncertainties may emerge that could have an impact on the forward-looking statements contained in this presentation. Forward-looking statements represent our management’s beliefs and assumptions only as of the date such statements are made. We undertake no obligation to update any forward-looking statements made in this presentation to reflect events or circumstances occurring after this presentation or to reflect new information or the occurrence of unanticipated events, except as required by law. ©2024 TWILIO INC. ALL RIGHTS RESERVED 12

Non-GAAP Financial Measures In addition to financial information presented in accordance with U.S. generally accepted accounting principles (“GAAP”), this presentation includes certain non-GAAP financial measures, including those listed below. We use these non-GAAP financial measures to evaluate our ongoing operations and for internal planning and forecasting purposes. We believe that these non-GAAP financial measures may be helpful to investors because they provide consistency and comparability with past financial performance, facilitate period-to-period comparisons of results of operations and assist in comparisons with other companies, many of which use similar non-GAAP financial measures to supplement their GAAP results. We believe organic revenue growth is useful in understanding the ongoing results of our operations. We believe free cash flow provides useful supplemental information to help investors understand underlying trends in our business and our liquidity. These non-GAAP financial measures are presented for supplemental informational purposes only, should not be considered substitutes for financial information presented in accordance with GAAP, and may be different from similarly-titled non-GAAP measures used by other companies. Non‑GAAP Income (Loss) from Operations. For the periods presented, we define non‑GAAP income (loss) from operations (which we also refer to as non-GAAP operating profit or non-GAAP operating loss, as applicable), adjusted to exclude, as applicable, stock-based compensation, amortization of acquired intangibles, loss on net assets divested, acquisition and divestiture related expenses, payroll taxes related to stock-based compensation, charitable contributions, restructuring costs, and impairment of long-lived assets. Organic Revenue. For the periods presented, we define organic revenue as GAAP revenue, excluding (i) revenue from each acquired business and revenue from application-to-person (“A2P”) 10DLC fees imposed by major U.S. carriers on our core messaging business, in each case until the beginning of the first full quarter following the one-year anniversary of the closing date of such acquisition or the initial date such fees were charged and (ii) revenue from each divested business beginning in the quarter of the closing date of such divestiture; provided that (a) if an acquisition closes or such fees are initially charged on the first day of a quarter, such revenue will be included in organic revenue beginning on the one-year anniversary of the closing date of such acquisition or the initial date such fees were charged and (b) if a divestiture closes on the last day of a quarter, such revenue will be included in organic revenue for that quarter. A2P 10DLC fees are fees imposed by U.S. mobile carriers for A2P SMS messages delivered to its subscribers, and we pass these fees to our messaging customers at cost. Organic Revenue Growth. For the periods presented, we calculate organic revenue growth by dividing (i) organic revenue for the period presented less organic revenue in the comparative period by (ii) organic revenue in the comparative period. If revenue from certain acquisitions, divestitures or A2P 10DLC fees is included or excluded in organic revenue in the period presented, then revenue from the same acquisitions, divestitures and A2P 10DLC fees is included or excluded in organic revenue in the comparative period for purposes of the denominator in the organic revenue growth calculation. As a result, the denominator used in this calculation will not always equal the organic revenue reported for the comparative period. Free Cash Flow. For the periods presented, we define free cash flow as net cash provided by (used in) operating activities excluding capitalized software development costs and purchases of long-lived and intangible assets. ©2024 TWILIO INC. ALL RIGHTS RESERVED 13

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