Cloudflare vs Tailscale: Founders, CEOs and History
Cloudflare was founded in 2009 by Matthew Prince, Michelle Zatlyn, Lee Holloway and is led by Matthew Prince. Tailscale was founded in 2019 by Avery Pennarun, David Crawshaw, David Carney and is led by Avery Pennarun.
Company facts
Cloudflare
- Founded
- 2009
- Headquarters
- San Francisco, California
- Current CEO
- Matthew Prince
- Employees
- 5,156
Tailscale
- Founded
- 2019
- Headquarters
- Toronto, Ontario, Canada (remote-first)
- Current CEO
- Avery Pennarun
- Employees
- 300
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.
Tailscale
Avery Pennarun
Avery Pennarun is co-founder and CEO of Tailscale. Before Tailscale he worked at Google, including on Google Fiber, and earlier built open-source tools and wrote widely read essays on engineering and product management.
David Crawshaw
David Crawshaw co-founded Tailscale in 2019 and served as its chief technology officer, building much of the early coordination server and client in Go. He previously worked at Google, including on the Go programming language.
David Carney
David Carney co-founded Tailscale in 2019 and was its chief operating officer at launch, based in Toronto. He worked with Pennarun and Crawshaw at Google before starting the company.
Brad Fitzpatrick
Brad Fitzpatrick created LiveJournal and the Memcached caching system, then spent years at Google working on the Go language. He left Google in January 2020 and joined Tailscale days later as a late-stage co-founder, working on the open-source Go client.
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
Has led Cloudflare's finance organization since 2017, including its 2019 IPO.
Source
Tailscale
- Avery Pennarun2019–present
Co-Founder & Chief Executive Officer
Co-founded Tailscale and sets its product and company strategy.
Source - David Crawshaw2019–present
Co-Founder
Built much of Tailscale's early coordination server and client architecture.
Source - Mike Shaver2026–present
VP of Engineering
Hired in July 2026 to scale engineering, replacing Andrew Mitchell.
Source - Ross Kukulinski2026–present
VP of Product
Leads product as Tailscale adds enterprise and AI features.
Source
Timeline: Cloudflare and Tailscale side by side
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.
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.
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.
2019Tailscale
Company founded
Founded by Pennarun, Crawshaw and Carney.
2020Cloudflare
Cloudflare One Launched
Cloudflare bundled its Zero Trust access, secure web gateway, and network services into Cloudflare One, its SASE platform.
2020Tailscale
Seed and Series A
$3 million seed in April; $12 million Series A led by Accel in November.
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.
2022Tailscale
Series B
$100 million led by CRV and Insight Partners.
2024Cloudflare
Revenue Reaches $1.67 Billion
Cloudflare reported 2024 revenue of $1.67 billion and free cash flow of $166.9 million.
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.
2025Tailscale
Series C
$160 million led by Accel at a reported ~$1.5 billion valuation.
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%.
2026Tailscale
Border0 joins Tailscale
Adds privileged access for production systems, databases and Kubernetes.
2026Tailscale
Pricing v4
Simplified plans and more predictable pricing.
2026Tailscale
Nearly 40,000 paying customers; Mike Shaver hired
Customer count roughly doubles since November 2025; new VP of Engineering appointed.
Acquisitions
Cloudflare
- Human Native2026Undisclosed
- Astro Technology Company2026Undisclosed
- VoidZero2026Undisclosed
- Replicate2025Undisclosed
- Nefeli Networks2024Undisclosed
- Baselime2024Undisclosed
Questions about Cloudflare vs Tailscale
Who is the CEO of Cloudflare, Inc. and Tailscale?
Cloudflare, Inc. is led by Matthew Prince and Tailscale is led by Avery Pennarun. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Cloudflare, Inc. founded vs Tailscale?
Cloudflare, Inc. was founded in 2009 — 10 years before Tailscale, which was founded in 2019. Cloudflare, Inc.'s longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Tailscale.
How many employees does Cloudflare, Inc. have compared to Tailscale?
Cloudflare, Inc. employs approximately 5,156 people, while Tailscale employs approximately 300. Cloudflare, Inc. has the larger workforce at 5,156 employees, compared to Tailscale's 300. 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 Tailscale headquartered?
Cloudflare, Inc. is headquartered in United States and Tailscale is headquartered in Canada. Their different home markets mean they may face different regulatory frameworks, tax regimes, and currency exposure.
Who founded Cloudflare, Inc. and Tailscale?
Cloudflare, Inc. was founded by Matthew Prince, Michelle Zatlyn, Lee Holloway. Tailscale was founded by Avery Pennarun, David Crawshaw, David Carney, Brad Fitzpatrick.
Which company has a longer operating history — Cloudflare, Inc. or Tailscale?
Cloudflare, Inc. has been operating for approximately 17 years, making it the more established of the two companies. Tailscale has been in operation for around 7 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 Tailscale overview