Tearsheet

Twilio (TWLO)


Market Price (2/21/2026): $112.91 | Market Cap: $17.3 Bil
Sector: Information Technology | Industry: Systems Software

Twilio (TWLO)


Market Price (2/21/2026): $112.91
Market Cap: $17.3 Bil
Sector: Information Technology
Industry: Systems Software

Investment Highlights Why It Matters Detailed financial logic regarding cash flow yields vs trend-riding momentum.

0 Attractive cash flow generation
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 17%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 16%
Expensive valuation multiples
P/EBITPrice/EBIT or Price/(Operating Income) ratio is 135x, P/EPrice/Earnings or Price/(Net Income) is 258x
1 Megatrend and thematic drivers
Megatrends include Cloud Computing, E-commerce & DTC Adoption, and Fintech & Digital Payments. Themes include Platform as a Service (PaaS), Show more.
Significant share based compensation
SBC/Rev LTMShare Based Compensation / Revenue (Sales), Last Twelve Months (LTM) is 12%
2  Yield minus risk free rate is negative
ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is -3.9%
3  Key risks
TWLO key risks include [1] significant profitability and margin pressures in its core messaging business, Show more.
0 Attractive cash flow generation
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 17%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 16%
1 Megatrend and thematic drivers
Megatrends include Cloud Computing, E-commerce & DTC Adoption, and Fintech & Digital Payments. Themes include Platform as a Service (PaaS), Show more.
2 Expensive valuation multiples
P/EBITPrice/EBIT or Price/(Operating Income) ratio is 135x, P/EPrice/Earnings or Price/(Net Income) is 258x
3 Significant share based compensation
SBC/Rev LTMShare Based Compensation / Revenue (Sales), Last Twelve Months (LTM) is 12%
4 Yield minus risk free rate is negative
ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is -3.9%
5 Key risks
TWLO key risks include [1] significant profitability and margin pressures in its core messaging business, Show more.

Valuation, Metrics & Events

Price Chart

Why The Stock Moved

Qualitative Assessment

AI Analysis | Feedback

Twilio (TWLO) stock has lost about 15% since 10/31/2025 because of the following key factors:

1. Decelerating Organic Revenue Growth Outlook: Despite beating Q4 2025 revenue and EPS estimates, Twilio's stock declined due to a projected slowdown in its core organic revenue growth. The company guided for organic revenue growth of 10-11% for Q1 2026 and 8-9% for the full fiscal year 2026, which is a decrease compared to the 12% organic growth reported in Q4 2025 and 13% for the full year 2025.

2. Significant Insider Selling Activity: A notable factor was the substantial insider selling, particularly by Director Andrew Stafman, who sold 1,000,000 shares for a total transaction amount of $129,000,000 on December 2, 2025. This sale contributed to over $135 million in insider sales during the last quarter (prior to February 13, 2026).

Show more

Stock Movement Drivers

Fundamental Drivers

The -16.1% change in TWLO stock from 10/31/2025 to 2/20/2026 was primarily driven by a -16.1% change in the company's P/E Multiple.
(LTM values as of)103120252202026Change
Stock Price ($)134.88113.14-16.1%
Change Contribution By: 
Total Revenues ($ Mil)4,8964,8960.0%
Net Income Margin (%)1.4%1.4%0.0%
P/E Multiple307.3257.7-16.1%
Shares Outstanding (Mil)1531530.0%
Cumulative Contribution-16.1%

LTM = Last Twelve Months as of date shown

Market Drivers

10/31/2025 to 2/20/2026
ReturnCorrelation
TWLO-16.1% 
Market (SPY)1.1%41.1%
Sector (XLK)-6.3%46.8%

Fundamental Drivers

The -12.3% change in TWLO stock from 7/31/2025 to 2/20/2026 was primarily driven by a -18.0% change in the company's P/S Multiple.
(LTM values as of)73120252202026Change
Stock Price ($)129.00113.14-12.3%
Change Contribution By: 
Total Revenues ($ Mil)4,5834,8966.8%
P/S Multiple4.33.5-18.0%
Shares Outstanding (Mil)1531530.1%
Cumulative Contribution-12.3%

LTM = Last Twelve Months as of date shown

Market Drivers

7/31/2025 to 2/20/2026
ReturnCorrelation
TWLO-12.3% 
Market (SPY)9.4%34.9%
Sector (XLK)7.4%36.2%

Fundamental Drivers

The -22.8% change in TWLO stock from 1/31/2025 to 2/20/2026 was primarily driven by a -34.2% change in the company's P/S Multiple.
(LTM values as of)13120252202026Change
Stock Price ($)146.58113.14-22.8%
Change Contribution By: 
Total Revenues ($ Mil)4,3394,89612.8%
P/S Multiple5.43.5-34.2%
Shares Outstanding (Mil)1591533.9%
Cumulative Contribution-22.8%

LTM = Last Twelve Months as of date shown

Market Drivers

1/31/2025 to 2/20/2026
ReturnCorrelation
TWLO-22.8% 
Market (SPY)15.6%52.2%
Sector (XLK)22.6%54.1%

Fundamental Drivers

The 89.1% change in TWLO stock from 1/31/2023 to 2/20/2026 was primarily driven by a 34.3% change in the company's Total Revenues ($ Mil).
(LTM values as of)13120232202026Change
Stock Price ($)59.84113.1489.1%
Change Contribution By: 
Total Revenues ($ Mil)3,6444,89634.3%
P/S Multiple3.03.517.3%
Shares Outstanding (Mil)18415320.0%
Cumulative Contribution89.1%

LTM = Last Twelve Months as of date shown

Market Drivers

1/31/2023 to 2/20/2026
ReturnCorrelation
TWLO89.1% 
Market (SPY)75.9%42.2%
Sector (XLK)111.5%40.0%

Return vs. Risk

Price Returns Compared

 202120222023202420252026Total [1]
Returns
TWLO Return-22%-81%55%42%32%-22%-67%
Peers Return16%-45%45%-19%1%4%-21%
S&P 500 Return27%-19%24%23%16%0%83%

Monthly Win Rates [3]
TWLO Win Rate33%17%50%58%50%0% 
Peers Win Rate67%33%58%48%50%40% 
S&P 500 Win Rate75%42%67%75%67%50% 

Max Drawdowns [4]
TWLO Max Drawdown-27%-84%-6%-30%-25%-24% 
Peers Max Drawdown-20%-56%-10%-28%-32%-15% 
S&P 500 Max Drawdown-1%-25%-1%-2%-15%-1% 


[1] Cumulative total returns since the beginning of 2021
[2] Peers: MDB, VRSN, OKTA, AKAM, CHOW. See TWLO Returns vs. Peers.
[3] Win Rate = % of calendar months in which monthly returns were positive
[4] Max drawdown represents maximum peak-to-trough decline within a year
[5] 2026 data is for the year up to 2/20/2026 (YTD)

How Low Can It Go

Unique KeyEventTWLOS&P 500
2022 Inflation Shock2022 Inflation Shock  
2022 Inflation Shock% Loss% Loss-90.4%-25.4%
2022 Inflation Shock% Gain to Breakeven% Gain to Breakeven937.6%34.1%
2022 Inflation ShockTime to BreakevenTime to BreakevenNot Fully Recovered days464 days
2020 Covid Pandemic2020 Covid Pandemic  
2020 Covid Pandemic% Loss% Loss-45.6%-33.9%
2020 Covid Pandemic% Gain to Breakeven% Gain to Breakeven84.0%51.3%
2020 Covid PandemicTime to BreakevenTime to Breakeven52 days148 days
2018 Correction2018 Correction  
2018 Correction% Loss% Loss-39.3%-19.8%
2018 Correction% Gain to Breakeven% Gain to Breakeven64.7%24.7%
2018 CorrectionTime to BreakevenTime to Breakeven182 days120 days

Compare to MDB, VRSN, OKTA, AKAM, CHOW

In The Past

Twilio's stock fell -90.4% during the 2022 Inflation Shock from a high on 2/18/2021. A -90.4% loss requires a 937.6% gain to breakeven.

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About Twilio (TWLO)

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 embed voice, messaging, video, and email capabilities into their applications. The company was incorporated in 2008 and is headquartered in San Francisco, California.

AI Analysis | Feedback

  • Twilio is like the **Stripe for communications**, providing APIs for developers to easily integrate voice, video, and messaging into their apps.
  • Think of Twilio as **AWS for communications infrastructure**, offering the cloud building blocks for companies to add calling, texting, and other communication features without managing complex telecom networks.

AI Analysis | Feedback

  • Twilio Programmable Messaging (SMS): Provides APIs for sending and receiving text messages, enabling notifications, alerts, and conversational interfaces for businesses.
  • Twilio Programmable Voice (Voice): Offers APIs to embed voice calling capabilities into applications, facilitating features like call routing, IVRs, and conference calls.
  • Twilio SendGrid (Email): A cloud-based platform for sending transactional and marketing emails at scale, focusing on deliverability and performance.
  • Twilio Flex (Contact Center): A customizable cloud-based contact center platform, allowing businesses to build tailored customer service experiences across multiple communication channels.
  • Twilio Programmable Video (Video): Delivers APIs for integrating real-time video and audio communication into applications, supporting various use cases from telehealth to education.
  • Twilio Verify (Authentication): An API for implementing multi-factor authentication (MFA) and user verification via SMS, voice, or email to enhance security and prevent fraud.

AI Analysis | Feedback

Twilio (symbol: TWLO) primarily sells its communication platform and services to other companies (Business-to-Business, or B2B). It provides developers with APIs to embed voice, video, messaging, and email capabilities into their applications. While Twilio has a highly diversified customer base and typically does not have individual customers representing a significant percentage of its total revenue, certain prominent public companies are widely known to be major users of its platform for their communication needs. These companies exemplify the types of organizations that rely on Twilio's services. Here are examples of such customer companies:
  • Uber Technologies, Inc. (NYSE: UBER) - Utilizes Twilio for connecting riders and drivers, sending notifications, and managing support communications.
  • Lyft, Inc. (NASDAQ: LYFT) - Similar to Uber, uses Twilio for facilitating communication between passengers and drivers, and for service alerts.
  • DoorDash, Inc. (NASDAQ: DASH) - Employs Twilio for coordinating deliveries between customers, dashers, and restaurants.
  • Block, Inc. (NYSE: SQ) - Formerly Square, uses Twilio for customer notifications, account verification, and other secure communications across its ecosystem of services (e.g., Square, Cash App).
  • Airbnb, Inc. (NASDAQ: ABNB) - Relies on Twilio for facilitating communication between hosts and guests, and for booking notifications.
  • Netflix, Inc. (NASDAQ: NFLX) - Uses Twilio for critical customer interactions such as account verification, password resets, and service notifications.
  • Shopify Inc. (NYSE: SHOP) - While merchants on Shopify's platform might directly integrate Twilio, Shopify itself, or its larger partners, use Twilio for various communication features related to e-commerce and customer engagement.
  • HubSpot, Inc. (NYSE: HUBS) - Integrates Twilio's capabilities to enhance communication features within its CRM, marketing, sales, and customer service platforms.

AI Analysis | Feedback

  • Amazon.com, Inc. (AMZN)
  • Alphabet Inc. (GOOGL)

AI Analysis | Feedback

Khozema Shipchandler Chief Executive Officer

Khozema Shipchandler was appointed CEO of Twilio in January 2024. He has over 25 years of experience in growing businesses and driving financial performance across global public organizations. Prior to his CEO appointment, he served as President of Twilio Communications from March 2023 to January 2024. He also held the roles of Chief Operating Officer at Twilio from October 2021 to October 2021 and Chief Financial Officer from November 2018 to October 2021. Before joining Twilio, Shipchandler spent over two decades at GE, where he held various financial and operating roles across Industrial Internet, Aviation, and Corporate Audit in the U.S., Middle East, and Singapore. His roles at GE included Chief Commercial Officer and Executive Vice President of Corporate Development at GE Digital, and Chief Financial Officer for the Middle East, North Africa & Turkey. He currently serves on the boards of Smartsheet and Ethos.

Aidan Viggiano Chief Financial Officer

Aidan Viggiano became Twilio's Chief Financial Officer in March 2023. She joined Twilio in 2019 as Vice President of Corporate Finance and was promoted to Senior Vice President of Finance in 2021, a role she held until 2023. Before her tenure at Twilio, Viggiano spent 16 years at General Electric, from 2003 to 2019, where she held various finance leadership positions, including Investor Relations and Chief of Staff to the CFO. She holds a B.S. in Economics from the Wharton School of the University of Pennsylvania.

Jeff Lawson Co-Founder (Former CEO and Chairman)

Jeff Lawson co-founded Twilio in 2008 and served as its CEO and Chairman until stepping down in January 2024. He is a serial entrepreneur, having founded Versity.com in 1998, which was later sold. He was also the founding CTO of StubHub and a co-founder and CTO of NineStar. Additionally, he contributed to the development of Amazon Web Services (AWS) during his time at Amazon. Lawson led Twilio through its initial public offering in 2016. In 2024, he acquired the satirical news site The Onion.

Christy Lake Chief People Officer

Christy Lake serves as the Chief People Officer at Twilio. In this role, she is responsible for the company's human resources strategies, which include driving talent acquisition, employee engagement, and organizational development initiatives. With a career spanning over two decades, Lake has held significant HR leadership roles at several companies, including Box, Medallia, and Hewlett-Packard.

Chris Koehler Chief Marketing Officer

Chris Koehler is the Chief Marketing Officer at Twilio, a position he assumed in May 2024. He oversees the company's global marketing strategies and is responsible for driving brand growth. Koehler brings a strong background in marketing and customer success, having held significant roles at companies such as Box and Adobe before joining Twilio.

AI Analysis | Feedback

Key Risks to Twilio (TWLO) Business:
  1. Profitability and Margin Pressures: Twilio faces challenges with thin profit margins, particularly in its core messaging business, which is impacted by rising carrier fees and cloud infrastructure costs. The company's profitability is also affected by slowing revenue growth and difficulties in improving overall margins, leading to investor concern regarding its long-term financial performance.
  2. Intense Competition and Commoditization: The Communications Platform as a Service (CPaaS) market is highly competitive, leading to pricing pressure and the commoditization of Twilio's foundational SMS offerings. Twilio competes with various CPaaS providers, over-the-top (OTT) messaging applications, and major cloud infrastructure providers, making it challenging to differentiate its services and sustain market share and revenue growth.
  3. Regulatory and Compliance Complexity: Operating across numerous international markets exposes Twilio to a dynamic and intricate web of data privacy laws (such as GDPR and CCPA), telecommunications regulations, and evolving mandates like Know Your Customer (KYC) requirements. Non-compliance with these diverse regulatory frameworks can lead to substantial financial penalties and operational disruptions, necessitating continuous investment in legal and compliance resources.

AI Analysis | Feedback

The primary clear emerging threat to Twilio comes from major cloud hyperscalers like Amazon Web Services (AWS) and Microsoft Azure directly competing in the Communications Platform as a Service (CPaaS) space.

AWS offers services such as AWS Chime SDK (for voice, video, and messaging capabilities) and AWS Pinpoint (for marketing and transactional SMS, voice, and email). Microsoft Azure provides Azure Communication Services (ACS), which offers similar APIs for voice, video, chat, and SMS.

These hyperscalers present a threat because they can offer deeply integrated communication services within their existing cloud ecosystems. Customers already heavily invested in AWS or Azure infrastructure may find it simpler, potentially more cost-effective (due to unified billing and reduced egress costs), and more efficient to leverage native communication services from their primary cloud provider rather than integrating a third-party CPaaS like Twilio. This trend could lead to Twilio being disintermediated from new projects, particularly for enterprises already deeply embedded in a specific cloud ecosystem, as the cloud providers build their own compelling communication layers.

AI Analysis | Feedback

Twilio (symbol: TWLO) operates within large and expanding addressable markets for its main products and services, primarily globally.

  • Overall Total Addressable Market (TAM): Twilio's total addressable market for communications and data is projected to reach approximately $119 billion by 2028, growing at an annual rate of 11% globally.

  • Expanded Total Addressable Market (TAM) with AI and CXaaS: By focusing on conversational AI and the Customer Experience as a Service (CXaaS) market, Twilio aims to expand its total addressable market to $158 billion by 2028 globally. This expansion includes an additional $39 billion driven by conversational AI and orchestration, covering areas such as Communications Platform as a Service (CPaaS), Contact Center as a Service (CCaaS), and Customer Data Platform (CDP).

While specific market sizes for individual products are often integrated into these broader categories, Twilio's main offerings contribute to these substantial global markets:

  • Communications Platform (CPaaS): This core offering includes programmable messaging (SMS, MMS, WhatsApp), voice, video, and email APIs. This is a significant component of the $119 billion global "communications and data" TAM.

  • Twilio Segment (Customer Data Platform - CDP): Segment helps businesses collect, clean, and activate customer data to create unified customer profiles. It underpins Twilio's customer engagement strategy and contributes to the larger CXaaS market.

  • Twilio Flex (Contact Center as a Service - CCaaS): Flex is a customizable cloud contact center platform. As part of the CXaaS market, it contributes to the projected $158 billion global TAM by 2028.

  • Twilio SendGrid (Email API and Marketing Campaigns): SendGrid provides email API services and marketing campaign tools, reliably delivering billions of emails monthly. Its market size is embedded within the broader communications and customer engagement markets, operating globally.

  • Twilio Engage (Marketing Automation Platform): Built on Twilio Segment and communication APIs, Engage is a growth automation platform for marketers. Its market size is part of the larger customer engagement and CXaaS markets.

AI Analysis | Feedback

Twilio (TWLO) is expected to drive future revenue growth over the next 2-3 years through several key strategies:
  • Expansion of AI-Powered Products and Solutions: Twilio is heavily focused on integrating artificial intelligence into its offerings, with management seeing sustained revenue growth potential from increased adoption of AI-powered voice, conversation management, and authentication tools. The company has reported explosive voice AI revenue growth, with voice AI adoption growing 60% year-over-year. These higher-margin AI use cases are expected to become a larger portion of the revenue mix, directly boosting overall profitability. Twilio's acquisition of Stytch, an identity platform, is also aimed at accelerating capabilities in digital trust and expanding into identity solutions for AI agents.
  • Growth in Customer Accounts and Increased Spending from Existing Customers: Twilio has demonstrated strong performance in growing its customer base, achieving a notable 22.5% year-over-year growth in customer accounts in Q3 2025. Furthermore, the company's Dollar-Based Net Expansion Rate (DBNER) of 109% in Q3 2025 (up from 108% in the previous quarter and 102% in Q2 2024) indicates that existing customers are increasing their spending on Twilio's platform. This expansion within the existing customer base, along with attracting new customers through self-serve and Independent Software Vendor (ISV) channels, is a significant driver.
  • Acceleration of Core Communication Services (Messaging and Voice): Despite the focus on AI, Twilio's core messaging and voice services continue to be strong revenue drivers. Messaging revenue grew in the high teens for the second consecutive quarter in Q3 2025, and voice revenue growth accelerated to the mid-teens, its fastest growth rate in over three years. The company continues to see broad-based strength across its product suite, with significant growth in both voice services and messaging.
  • International Expansion: Twilio's CEO, Khozema Shipchandler, has emphasized the company's strategic focus on international expansion as a key driver for future growth. This is further supported by strong growth observed in messaging internationally.

AI Analysis | Feedback

Share Repurchases

  • Twilio authorized a $1.0 billion share repurchase program in February 2023, set to expire on December 31, 2024.
  • An additional $2.0 billion share repurchase program was authorized in March 2024, also expiring by December 31, 2024. By that time, nearly $800 million had already been repurchased from the initial program, with a target to complete both programs, totaling approximately $2.2 billion in further repurchases, by the end of 2024.
  • In January 2025, a new $2.0 billion share repurchase program was authorized, slated to expire on December 31, 2027. By September 30, 2025, Twilio had repurchased $670.5 million under this program, with approximately $1.3 billion remaining.

Share Issuance

  • In August 2020, Twilio commenced an underwritten public offering of $1.25 billion of Class A common stock.
  • Twilio announced the pricing of an upsized $1.54 billion public offering of Class A common stock in February 2021.
  • A follow-on offering in May 2021 raised an additional $1.8 billion.

Outbound Investments

  • Twilio acquired Segment, a customer data platform, for approximately $3.2 billion in an all-stock deal in October 2020.
  • In May 2021, Twilio acquired Ionic Security, a cloud data security solutions provider, and Zipwhip, a text messaging platform, for undisclosed amounts.
  • Twilio has made 25 investments across various sectors, with its most recent being a Series B round in Hyro on December 10, 2024.

Better Bets vs. Twilio (TWLO)

Latest Trefis Analyses

Trade Ideas

Select ideas related to TWLO.

Unique KeyDateTickerCompanyCategoryTrade Strategy6M Fwd Rtn12M Fwd Rtn12M Max DD
ROP_1302026_Dip_Buyer_FCFYield01302026ROPRoper TechnologiesDip BuyDB | FCFY OPMDip Buy with High FCF Yield and High Margin
Buying dips for companies with high FCF yield and meaningfully high operating margin
-13.4%-13.4%-13.8%
TDC_1302026_Dip_Buyer_FCFYield01302026TDCTeradataDip BuyDB | FCFY OPMDip Buy with High FCF Yield and High Margin
Buying dips for companies with high FCF yield and meaningfully high operating margin
17.7%17.7%-8.7%
CVLT_1302026_Dip_Buyer_High_CFO_Margins_ExInd_DE01302026CVLTCommVault SystemsDip BuyDB | CFO/Rev | Low D/EDip Buy with High Cash Flow Margins
Buying dips for companies with significant cash flows from operations and reasonable debt / market cap
2.3%2.3%-5.1%
NTNX_1302026_Dip_Buyer_High_CFO_Margins_ExInd_DE01302026NTNXNutanixDip BuyDB | CFO/Rev | Low D/EDip Buy with High Cash Flow Margins
Buying dips for companies with significant cash flows from operations and reasonable debt / market cap
6.2%6.2%-6.3%
FICO_1302026_Monopoly_xInd_xCD_Getting_Cheaper01302026FICOFair IsaacMonopolyMY | Getting CheaperMonopoly-Like with P/S Decline
Large cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple
-8.1%-8.1%-9.2%

Recent Active Movers

Peer Comparisons

Peers to compare with:

Financials

TWLOMDBVRSNOKTAAKAMCHOWMedian
NameTwilio MongoDB VeriSign Okta Akamai T.ChowChow. 
Mkt Price113.14344.56215.9174.2994.170.75103.66
Mkt Cap17.328.019.913.113.5-17.3
Rev LTM4,8962,3171,6572,8404,133-2,840
Op Inc LTM128-1561,121122637-128
FCF LTM7833461,068895718-783
FCF 3Y Avg545194917634740-634
CFO LTM8403761,0919121,496-912
CFO 3Y Avg6012089496551,454-655

Growth & Margins

TWLOMDBVRSNOKTAAKAMCHOWMedian
NameTwilio MongoDB VeriSign Okta Akamai T.ChowChow. 
Rev Chg LTM12.8%20.9%6.4%12.1%4.2%-12.1%
Rev Chg 3Y Avg10.4%25.0%5.2%18.1%4.8%-10.4%
Rev Chg Q14.7%18.7%7.6%11.6%5.0%-11.6%
QoQ Delta Rev Chg LTM3.5%4.5%1.8%2.8%1.2%-2.8%
Op Mgn LTM2.6%-6.7%67.7%4.3%15.4%-4.3%
Op Mgn 3Y Avg-4.5%-11.9%67.5%-8.8%16.8%--4.5%
QoQ Delta Op Mgn LTM0.9%0.7%0.0%1.3%0.0%-0.7%
CFO/Rev LTM17.2%16.2%65.9%32.1%36.2%-32.1%
CFO/Rev 3Y Avg13.2%10.0%60.3%25.5%36.8%-25.5%
FCF/Rev LTM16.0%14.9%64.5%31.5%17.4%-17.4%
FCF/Rev 3Y Avg11.9%9.4%58.3%24.6%18.7%-18.7%

Valuation

TWLOMDBVRSNOKTAAKAMCHOWMedian
NameTwilio MongoDB VeriSign Okta Akamai T.ChowChow. 
Mkt Cap17.328.019.913.113.5-17.3
P/S3.512.112.04.63.3-4.6
P/EBIT135.3-425.217.459.619.7-19.7
P/E257.7-395.824.167.326.7-26.7
P/CFO20.674.618.314.49.0-18.3
Total Yield0.4%-0.3%4.9%1.5%3.7%-1.5%
Dividend Yield0.0%0.0%0.7%0.0%0.0%-0.0%
FCF Yield 3Y Avg2.9%0.7%4.3%4.4%5.1%-4.3%
D/E0.10.00.10.00.4-0.1
Net D/E-0.1-0.10.1-0.20.3--0.1

Returns

TWLOMDBVRSNOKTAAKAMCHOWMedian
NameTwilio MongoDB VeriSign Okta Akamai T.ChowChow. 
1M Rtn-5.9%-9.7%-14.3%-16.5%0.5%9.7%-7.8%
3M Rtn-6.2%7.3%-13.8%-5.6%5.8%-92.0%-5.9%
6M Rtn6.4%57.3%-19.4%-19.3%21.3%-91.2%-6.5%
12M Rtn-4.1%18.8%-6.5%-22.0%-3.9%-91.2%-5.3%
3Y Rtn70.2%63.6%7.2%2.9%23.3%-91.2%15.2%
1M Excs Rtn-6.4%-10.2%-14.8%-17.0%-0.0%9.2%-8.3%
3M Excs Rtn-10.7%-2.4%-17.6%-12.7%2.9%-96.7%-11.7%
6M Excs Rtn3.0%54.0%-27.9%-26.4%15.8%-99.3%-11.7%
12M Excs Rtn-19.1%4.3%-18.1%-35.9%-18.5%-103.7%-18.8%
3Y Excs Rtn15.1%-16.5%-64.8%-70.9%-59.8%-158.3%-62.3%

Financials

Segment Financials

Revenue by Segment
$ Mil20242023202220212020
Twilio Communications (Communications)3,8593,5502,411  
Twilio Segment (Segment)295276   
Other  105  
Software  326  
Single segment   1,7621,134
Total4,1543,8262,8421,7621,134


Operating Income by Segment
$ Mil20242023202220212020
Twilio Communications (Communications)842    
Acquisition and divestiture related expenses-6    
Payroll taxes related to stock-based compensation-13    
Charitable contributions-17    
Loss on net assets divested-32    
Twilio Segment (Segment)-72    
Restructuring costs-166    
Amortization of acquired intangibles-192    
Corporate costs not allocated to segments-237    
Impairment of long-lived assets-321    
Stock-based compensation-663    
Total-877    


Price Behavior

Price Behavior
Market Price$113.14 
Market Cap ($ Bil)17.3 
First Trading Date06/23/2016 
Distance from 52W High-21.5% 
   50 Days200 Days
DMA Price$127.70$118.50
DMA Trendupdown
Distance from DMA-11.4%-4.5%
 3M1YR
Volatility47.0%55.3%
Downside Capture220.73183.53
Upside Capture128.47155.50
Correlation (SPY)32.3%54.1%
TWLO Betas & Captures as of 1/31/2026

 1M2M3M6M1Y3Y
Beta0.820.561.341.611.511.38
Up Beta0.431.291.971.421.371.29
Down Beta-1.20-0.520.781.051.531.45
Up Capture47%67%103%177%175%306%
Bmk +ve Days11223471142430
Stock +ve Days9213262126389
Down Capture481%151%173%190%140%108%
Bmk -ve Days9192754109321
Stock -ve Days11202963124360

[1] Upside and downside betas calculated using positive and negative benchmark daily returns respectively
Based On 1-Year Data
Annualized
Return
Annualized
Volatility
Sharpe
Ratio
Correlation
with TWLO
TWLO-10.5%55.1%-0.00-
Sector ETF (XLK)17.0%27.5%0.5557.2%
Equity (SPY)13.5%19.4%0.5354.8%
Gold (GLD)74.5%25.6%2.150.4%
Commodities (DBC)7.2%16.9%0.2516.8%
Real Estate (VNQ)7.1%16.7%0.2433.5%
Bitcoin (BTCUSD)-30.6%44.9%-0.6831.2%

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Based On 5-Year Data
Annualized
Return
Annualized
Volatility
Sharpe
Ratio
Correlation
with TWLO
TWLO-24.3%58.8%-0.23-
Sector ETF (XLK)16.1%24.8%0.5950.1%
Equity (SPY)13.4%17.0%0.6249.0%
Gold (GLD)22.6%17.1%1.083.2%
Commodities (DBC)10.9%19.0%0.465.4%
Real Estate (VNQ)5.0%18.8%0.1733.7%
Bitcoin (BTCUSD)7.2%57.1%0.3524.1%

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Based On 10-Year Data
Annualized
Return
Annualized
Volatility
Sharpe
Ratio
Correlation
with TWLO
TWLO14.2%60.4%0.48-
Sector ETF (XLK)23.3%24.2%0.8847.0%
Equity (SPY)16.1%17.9%0.7743.3%
Gold (GLD)14.8%15.6%0.794.1%
Commodities (DBC)8.6%17.6%0.4010.3%
Real Estate (VNQ)7.0%20.7%0.3027.1%
Bitcoin (BTCUSD)67.8%66.7%1.0715.3%

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Short Interest

Short Interest: As Of Date1302026
Short Interest: Shares Quantity6.1 Mil
Short Interest: % Change Since 11520263.0%
Average Daily Volume2.4 Mil
Days-to-Cover Short Interest2.5 days
Basic Shares Quantity153.1 Mil
Short % of Basic Shares4.0%

Earnings Returns History

Expand for More
 Forward Returns
Earnings Date1D Returns5D Returns21D Returns
2/12/20262.3%2.5% 
10/30/202519.5%13.0%15.0%
8/7/2025-19.4%-17.6%-10.9%
5/1/20252.3%7.5%22.2%
1/23/202520.1%30.8%4.1%
10/30/202414.3%28.0%48.1%
8/1/202411.7%7.7%11.5%
5/7/2024-7.5%-1.8%-9.5%
...
SUMMARY STATS   
# Positive121010
# Negative131514
Median Positive5.0%12.2%14.7%
Median Negative-9.4%-11.7%-14.3%
Max Positive39.6%53.1%60.7%
Max Negative-34.6%-22.4%-34.4%

SEC Filings

Expand for More
Report DateFiling DateFiling
09/30/202510/31/202510-Q
06/30/202508/08/202510-Q
03/31/202505/02/202510-Q
12/31/202402/26/202510-K
09/30/202410/31/202410-Q
06/30/202408/01/202410-Q
03/31/202405/08/202410-Q
12/31/202302/27/202410-K
09/30/202311/09/202310-Q
06/30/202308/09/202310-Q
03/31/202305/10/202310-Q
12/31/202202/27/202310-K
09/30/202211/04/202210-Q
06/30/202208/05/202210-Q
03/31/202205/05/202210-Q
12/31/202102/22/202210-K

Insider Activity

Expand for More
#OwnerTitleHoldingActionFiling DatePriceSharesTransacted
Value
Value of
Held Shares
Form
1Viggiano, AidanChief Financial OfficerDirectSell1072026135.977,213980,75215,260,729Form
2Viggiano, AidanChief Financial OfficerDirectSell1052026143.388,1091,162,67017,126,622Form
3Shipchandler, KhozemaChief Executive OfficerDirectSell1052026143.3713,2661,901,94829,694,385Form
4Stafman, AndrewSee footnotesSell12022025129.001,000,000129,000,000296,055,000Form
5Viggiano, AidanChief Financial OfficerDirectSell11212025120.7054665,90215,396,251Form

TWLO Trade Sentinel


Core Investment Debate

The Segment Growth Engine vs. Core Commoditization

BULL VIEW

A strategic mix shift to the 'Segment' data platform will expand margins and re-accelerate growth, proving Twilio is a customer engagement platform, not a utility.

CORE TENSION

Can the high-margin 'Data & Applications' business grow fast enough to offset the commoditization and margin pressure in the core 'Communications' business?


PREVAILING SENTIMENT
BEARISH

The 'Segment' (Customer Data Platform) business unit's revenue declined by 1% year-over-year in the most recently reported quarter (Q4 2024), while the core business grew.

BEAR VIEW

The 'Segment' acquisition is failing to deliver growth, leaving the company exposed to intense pricing pressure from competitors and hyperscalers in its core, low-margin business.

Next 6 months: Risks and Catalysts
Timeline Event & Metric To Watch
Feb 12, 2026
Q4 2025 Earnings Report
Watch: Growth rate of the 'Segment' (Data & Applications) business. A figure below high single-digits is a major failure signal.
Feb 12, 2026
Q1 2026 Gross Margin Guidance
Watch: Commentary on 'gross margin' and 'carrier fees'. Any downward revision to margin guidance is a negative trigger.
Next 6 Months
Hyperscaler Developer Conferences
Watch: Announcements of new features, pricing, or bundling for Azure Communication Services or AWS Pinpoint.
Ongoing
Major Tech Sector Earnings Calls
Watch: Announcements of further headcount reductions or hiring freezes from large tech employers, a core Twilio customer base.
Key Events in Last 6 Months
Date Event Stock Impact
8/7/2025
Q2 2025 Earnings Report
Details: Despite meeting revenue expectations, the company reported a year-over-year decline in gross margins, citing rising carrier fees, which led to a sharp stock sell-off.
Plummeted -19.38%
$122.39 -> $98.67
9/18/2025
Announces Major Enterprise Win
Details: The company announced a new contract with 'Global Bank X' for its fraud detection API, signaling strength in high-value enterprise use cases.
Rose significantly by 4.68%
$103.53 -> $108.38
10/30/2025
Q3 2025 Earnings Report
Details: Twilio reported accelerating active customer accounts and dollar-based net expansion rate, significantly beating expectations and causing the stock to surge in the following session.
Surged +19.51%
$112.86 -> $134.88
12/30/2025
Stock Reaches 6-Month High
Details: The stock reached its highest point in the trailing 6-month period, driven by broad market strength and momentum from its strong Q3 earnings report.
Modest 1.85% gain
$141.52 -> $144.14
1/15/2026
Mass Arbitration Claims Surface
Details: Reports emerged of mass arbitration claims alleging improper data collection via Twilio's SDKs. Stock fell on concerns of unquantified legal and financial liabilities.
Fell notably by -2.64%
$123.03 -> $119.78
Risk Management
Position Sizing

1% - 3%

CONSERVATIVE

Stock is in an Explosive Volatility regime (4.6x S&P). The Bearish sentiment, eroding moat, and low near-term visibility create a high-risk profile, forcing a Conservative sizing until the fundamental picture improves.

Diversification Alternatives
VEEV
SECTOR

Unlike TWLO's commoditizing business, VEEV has a strong regulatory moat in Life Sciences SaaS, leading to high switching costs and superior pricing power.

Core Thesis: The core thesis is built on the digitization of the life sciences industry, where VEEV is the entrenched, mission-critical platform for R&D and commercial operations.
DDOG
SECTOR

DDOG's integrated, vendor-neutral observability platform has a stronger position against hyperscalers than TWLO, serving as a necessary multi-cloud aggregation layer.

Core Thesis: The increasing complexity of cloud applications creates a durable demand for a best-of-breed observability platform, driving strong net revenue retention.
Stock Conviction

AVOID (Score 1-2)

CONVICTION RATIONALE

The risk-reward is highly unattractive with a probability-adjusted skew of 0.36x. The investment thesis requires believing in a turnaround of the 'Segment' business, but the hard data shows a -1% YoY decline. The moat is eroding in the core business, and the valuation does not adequately compensate for the high probability that the turnaround strategy will fail.

STOCK ARCHETYPE
Turnaround / Deep Value

Twilio is no longer a 'High-Beta Compounder' as growth has materially decelerated. The investment thesis now hinges entirely on the successful execution of a strategic pivot from its commoditizing core 'Communications' business to the higher-margin 'Data & Applications' segment. This places the focus squarely on strategic execution and management's ability to right the ship, fitting the 'Turnaround' archetype.

INVESTMENT THESIS
Data & Applications Segment Margin Mix Shift and FCF Inflection

The primary long thesis is a margin expansion and free cash flow story, driven by a successful strategic shift. As the business mix skews towards the higher-margin 'Data & Applications' (Segment) business, overall profitability should improve significantly, leading to substantial EPS growth and FCF generation even with decelerating top-line growth.

Mechanism: Each dollar of revenue shifted from the ~50% gross margin 'Communications' business to the ~75% gross margin 'Data & Applications' business directly enhances corporate gross profit. This, combined with operating discipline, expands operating margins and accelerates free cash flow conversion, which is then returned to shareholders via buybacks.
Supporting Evidence:
  • 'Data & Applications' Gross Margin is ~75% vs. 'Communications' at ~50%.
  • Management has shifted capital allocation priorities to FCF generation, with guidance for $920M-$930M in 2025, up from $657M in 2024.
  • The company has a significant opportunity for operating margin expansion from 18% towards a mature SaaS peer level of 25-30%.
PRIMARY RISK
Failure of 'Segment' Business Unit to Gain Traction

The greatest risk to the thesis is the persistent failure of the 'Segment' (Customer Data Platform) business to achieve escape velocity. Recent data shows this unit's revenue declined 1% YoY, directly contradicting the 'Alpha Driver'. If Segment cannot become a reliable growth engine, Twilio is left with a structurally challenged, commoditizing core business with limited pricing power.

Mechanism: If the Segment business fails to grow, the mix-shift thesis breaks. Twilio's valuation would then need to be re-rated downwards from a hopeful SaaS multiple to that of a low-growth, low-margin communications utility, causing significant multiple compression.
Supporting Evidence:
  • The 'Segment' business unit's revenue declined by 1% year-over-year in Q4 2024.
  • The risk of 'Structural Stagnation of Segment' is rated as CRITICAL with a HIGH likelihood in the next 6 months.
  • Intense competition in the Customer Data Platform market is preventing Segment from gaining market share.
Key KPI Watchlist
KPI Threshold Rationale
Data & Applications (Segment) Revenue Growth YoY>10%This is the single most important leading indicator for the Alpha Driver. Any number below high single digits confirms the turnaround is failing.
Non-GAAP Gross MarginStable or ExpandingMeasures the impact of commoditization and carrier fees in the core business. A declining margin would signal pricing power is deteriorating faster than the mix-shift can offset.
Dollar-Based Net Expansion Rate>105%While this metric has decelerated, a drop below 100% would indicate net customer churn, a significant red flag for the health of the existing customer base.