Cloudflare vs Twilio: Founders, CEOs and History
Cloudflare was founded in 2009 by Matthew Prince, Michelle Zatlyn, Lee Holloway and is led by Matthew Prince. Twilio was founded in 2008 by Jeff Lawson, John Wolthuis, Evan Cooke and is led by Khozema Shipchandler.
Company facts
Cloudflare
- Founded
- 2009
- Headquarters
- San Francisco, California
- Current CEO
- Matthew Prince
- Employees
- 5,156
Twilio
- Founded
- 2008
- Headquarters
- San Francisco, California, United States
- Current CEO
- Khozema Shipchandler
- Employees
- 5,492
Founders
Cloudflare
Matthew Prince
Matthew Prince is Cloudflare's co-founder, CEO, and board chair. In 2004 he and Lee Holloway built Project Honey Pot, which let website owners track spammers harvesting email addresses but could not stop them.
Michelle Zatlyn
Michelle Zatlyn is Cloudflare's co-founder, President, and Chief Operating Officer, and a member of its board. She met Matthew Prince at Harvard Business School, where the two developed the business plan that became Cloudflare in 2009.
Lee Holloway
Lee Holloway co-founded Cloudflare in 2009 and was its first lead engineer and systems architect. He had earlier built Project Honey Pot with Matthew Prince starting in 2004, and he designed much of Cloudflare's early software infrastructure.
Twilio
Jeff Lawson
Jeff Lawson co-founded Twilio in 2008 and was CEO until January 2024, leading it through its 2016 IPO and the SendGrid and Segment acquisitions. He wrote Ask Your Developer (2021) about developer-led software.
John Wolthuis
John Wolthuis co-founded Twilio in 2008. He architected the initial telephony backend that allowed developers to send text messages and make phone calls using a simple web API.
Evan Cooke
Evan Cooke co-founded Twilio and served as its first CTO. He was instrumental in designing the company's highly reliable cloud architecture, ensuring the API could scale to handle massive, instantaneous spikes in SMS traffic (such as during Uber surges or Airb…
CEOs and their tenures
Cloudflare
- Matthew Prince2009–present
Co-Founder, Chief Executive Officer, and Chair
Co-founded Cloudflare in 2009, led it through its September 2019 NYSE IPO, and has grown annual revenue past $2 billion (2025) while expanding from web security into Zero Trust, developer, and AI services.
Source - Michelle Zatlyn2009–present
Co-Founder, President, and Chief Operating Officer
Co-founded Cloudflare in 2009 with Matthew Prince and Lee Holloway and, as President and COO, has led operations and company-building as Cloudflare scaled to more than 5,000 employees.
Source - Thomas Seifert2017–present
Chief Financial Officer
As CFO, he consistently delivered high revenue growth while carefully controlling capital expenditures, allowing Cloudflare to heavily invest in its serverless Edge computing network.
Source
Twilio
- Jeff Lawson2008–2024
Co-founder and CEO
As the long-time CEO, he aggressively scaled the company into a $60 billion behemoth before intense pressure from activist investors forced him to resign in 2024 following growth stagnation.
Source - Aidan Viggiano2023–present
Chief Financial Officer
As CFO, she strictly enforces the new profitability mandates, cutting massive amounts of real estate and software expenses across the enterprise.
Source - Khozema Shipchandler2024–present
Chief Executive Officer
Taking over as CEO in 2024, he shifted the company's focus away from unprofitable hyper-growth toward heavily optimizing the highly lucrative core communications platform.
Source
Timeline: Cloudflare and Twilio side by side
2008Twilio
Company Founded
Jeff Lawson, Evan Cooke, and John Wolthuis founded Twilio and launched its first voice API for developers.
2009Cloudflare
Cloudflare Founded
Matthew Prince, Michelle Zatlyn, and Lee Holloway founded Cloudflare, building on the Project Honey Pot spam-tracking project.
2010Cloudflare
TechCrunch Disrupt Launch
Cloudflare launched publicly at TechCrunch Disrupt in San Francisco in September 2010, offering free website protection and acceleration.
2010Twilio
SMS API Launched
Twilio added programmable SMS, which became its largest product line.
2014Cloudflare
Universal SSL and Project Galileo
Cloudflare gave free SSL certificates to all customers with Universal SSL and launched Project Galileo to protect at-risk nonprofits and journalists for free.
2015Twilio
Authy Acquired
Twilio acquired the two-factor authentication company Authy in 2015.
2016Twilio
NYSE IPO
Twilio listed on the NYSE under the ticker TWLO in June 2016, pricing shares at $15.
2017Cloudflare
Cloudflare Workers Announced
Cloudflare introduced Workers, a serverless platform built on V8 isolates that lets developers run code across its network.
2019Cloudflare
NYSE IPO
Cloudflare completed its IPO on the New York Stock Exchange under the ticker NET in September 2019 at $15 per share, raising about $525 million.
2019Twilio
SendGrid Acquisition
Twilio completed its all-stock acquisition of email platform SendGrid, announced at about $2 billion.
2020Cloudflare
Cloudflare One Launched
Cloudflare bundled its Zero Trust access, secure web gateway, and network services into Cloudflare One, its SASE platform.
2020Twilio
Segment Acquisition
Twilio acquired customer data platform Segment for about $3.2 billion, its largest deal.
2021Twilio
Revenue Passes $2.8 Billion
Twilio reported FY2021 revenue of $2.842 billion, up 61% year over year, with a net loss of $949.9 million.
2022Cloudflare
Area 1 Security and R2 General Availability
Cloudflare acquired email security company Area 1 Security for about $162 million and made R2 zero-egress object storage generally available.
2023Twilio
Restructuring
Twilio cut about 17% of its workforce in February 2023 and made further reductions later in the year as it shifted toward profitability.
2024Cloudflare
Revenue Reaches $1.67 Billion
Cloudflare reported 2024 revenue of $1.67 billion and free cash flow of $166.9 million.
2024Twilio
CEO Transition
Co-founder Jeff Lawson stepped down as CEO in January 2024 and Khozema Shipchandler succeeded him.
2025Cloudflare
Revenue Passes $2 Billion
Cloudflare reported 2025 revenue of $2.17 billion (+29.8%) and closed its largest contract ever, averaging $42.5 million per year in ACV.
2025Twilio
First Full-Year GAAP Profit and Stytch Deal
Twilio reported FY2025 revenue of $5.067 billion and net income of $33.8 million, and completed its acquisition of identity platform Stytch on November 14, 2025.
2026Cloudflare
VoidZero Acquisition and Growth Acceleration
Cloudflare acquired VoidZero, the company behind the Vite JavaScript tooling ecosystem, in June 2026 and reported Q2 2026 revenue growth of 36%.
2026Twilio
Growth Re-accelerates
Twilio reported Q2 2026 revenue of $1.50 billion, up 22%, and raised its 2026 revenue growth outlook to 18%-18.5%.
Acquisitions
Cloudflare
- Human Native2026Undisclosed
- Astro Technology Company2026Undisclosed
- VoidZero2026Undisclosed
- Replicate2025Undisclosed
- Nefeli Networks2024Undisclosed
- Baselime2024Undisclosed
Questions about Cloudflare vs Twilio
Who is the CEO of Cloudflare, Inc. and Twilio Inc.?
Cloudflare, Inc. is led by Matthew Prince and Twilio Inc. is led by Khozema Shipchandler. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Cloudflare, Inc. founded vs Twilio Inc.?
Twilio Inc. was founded in 2008 — 1 year before Cloudflare, Inc., which was founded in 2009. Twilio Inc.'s longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Cloudflare, Inc..
How many employees does Cloudflare, Inc. have compared to Twilio Inc.?
Cloudflare, Inc. employs approximately 5,156 people, while Twilio Inc. employs approximately 5,492. Twilio Inc. has the larger workforce at 5,492 employees, compared to Cloudflare, Inc.'s 5,156. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are Cloudflare, Inc. and Twilio Inc. headquartered?
Both Cloudflare, Inc. and Twilio Inc. are headquartered in United States, meaning they operate under the same primary regulatory and tax environment.
Who founded Cloudflare, Inc. and Twilio Inc.?
Cloudflare, Inc. was founded by Matthew Prince, Michelle Zatlyn, Lee Holloway. Twilio Inc. was founded by Jeff Lawson, John Wolthuis, Evan Cooke.
Which company has a longer operating history — Cloudflare, Inc. or Twilio Inc.?
Twilio Inc. has been operating for approximately 18 years, making it the more established of the two companies. Cloudflare, Inc. has been in operation for around 17 years. A longer operating history often signals greater institutional resilience and brand recognition, though it can also mean slower adaptation to new market conditions.
Figures come from each company's filings and the sources linked beside them. Amounts reported in another currency are shown in US dollars at an approximate rate and marked with ~. Back to the Cloudflare vs Twilio overview