Okta vs Tailscale: Founders, CEOs and History
Okta was founded in 2009 by Todd McKinnon, Frederic Kerrest and is led by Todd McKinnon. Tailscale was founded in 2019 by Avery Pennarun, David Crawshaw, David Carney and is led by Avery Pennarun.
Company facts
Founders
Okta
Todd McKinnon
Todd McKinnon co-founded Okta in 2009 and has been its CEO since the start. At Salesforce he ran engineering during its early growth, which shaped his view that SaaS adoption would make identity, not the network perimeter, the core of enterprise security.
Frederic Kerrest
Frederic Kerrest co-founded Okta with Todd McKinnon in 2009 and led its early sales, partnerships and operations as chief operating officer, later serving as executive vice chairman.
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. Serving as the absolutely critical initial backend architect, he helped design the highly robust, incredibly scalable control plane that allows millions of distributed devices to instantly discover and connect to each…
Brad Fitzpatrick
Brad Fitzpatrick created LiveJournal and the Memcached caching system, then spent years at Google working on the Go language.
CEOs and their tenures
Okta
- Todd McKinnon2009–present
Co-Founder & Chief Executive Officer
Has led Okta since founding, through its 2017 IPO, the 2021 Auth0 deal and its turn to GAAP profitability in fiscal 2025.
Source - Frederic Kerrest2009–2023
Co-Founder; former COO and Executive Vice Chairman
As Co-Founder and Vice Chairman, he provided the absolutely essential business and sales acumen required to scale the company, perfectly complementing Todd McKinnon's technical expertise.
Source - Brett Tighe2022–present
Chief Financial Officer
Oversaw margin expansion to a 30% free cash flow margin in fiscal 2026, the cash settlement of the 2026 convertible notes and the share buyback.
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
As Co-Founder and CTO, he is the absolute visionary behind the platform's incredibly elegant, peer-to-peer routing architecture.
Source - Mike Shaver2026–present
VP of Engineering
As an early executive and key operational leader, he helped translate deep, complex networking technology into an incredibly simple, highly commercial B2B product.
Source - Ross Kukulinski2026–present
VP of Product
As a senior product leader, he manages the absolute critical roadmap required to secure highly lucrative, multi-million dollar contracts with Fortune 500 CISOs.
Source
Timeline: Okta and Tailscale side by side
2009Okta
Founded as Saasure in San Francisco
Todd McKinnon and Frederic Kerrest start the company; it is soon renamed Okta.
2015Okta
$1.2 Billion Valuation
Okta raised $75 million in September 2015 at a valuation of about $1.2 billion.
2017Okta
Nasdaq IPO (OKTA)
Okta lists in April 2017 at $17 per share, raising about $187 million.
2019Okta
Azuqua Acquired
Okta bought the workflow-automation company Azuqua in 2019 for about $52.5 million.
2019Tailscale
Company founded
Founded by Pennarun, Crawshaw and Carney.
2020Tailscale
Seed and Series A
$3 million seed in April; $12 million Series A led by Accel in November.
2021Okta
Auth0 acquisition closes
Okta completes its roughly $6.5 billion all-stock purchase of Auth0 in May 2021, adding customer identity.
2022Okta
Lapsus$ Breach
Okta disclosed in March 2022 that the Lapsus$ group had accessed a support engineer's laptop at a contractor.
2022Tailscale
Series B
$100 million led by CRV and Insight Partners.
2023Okta
Support system breach
An October 2023 compromise of Okta's customer support system exposed customer data and hurt trust.
2023Okta
Acquired Spera Security
Okta acquired Spera Security.
2025Okta
First full year of GAAP profit
Fiscal 2025 revenue reaches $2.610 billion with $28 million of GAAP net income.
2025Okta
Acquired Axiom Security
Okta acquired Axiom Security.
2025Tailscale
Series C
$160 million led by Accel at a reported ~$1.5 billion valuation.
2026Okta
Fiscal 2026: $2.919B revenue, $235M net income
Revenue grows 12% and free cash flow reaches $863 million.
2026Okta
Permiso deal and Okta for AI Agents
Okta agrees to buy Permiso Security in July 2026 and launches AI agent identity products at Oktane in September 2026.
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
Okta
- Permiso Security2026Undisclosed
- Axiom Security2025Undisclosed
- Spera Security2023Undisclosed
- Auth02021$6.5B
Questions about Okta vs Tailscale
Who is the CEO of Okta, Inc. and Tailscale?
Okta, Inc. is led by Todd McKinnon 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 Okta, Inc. founded vs Tailscale?
Okta, Inc. was founded in 2009 — 10 years before Tailscale, which was founded in 2019. Okta, 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 Okta, Inc. have compared to Tailscale?
Okta, Inc. employs approximately 6,366 people, while Tailscale employs approximately 300. Okta, Inc. has the larger workforce at 6,366 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 Okta, Inc. and Tailscale headquartered?
Okta, 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 Okta, Inc. and Tailscale?
Okta, Inc. was founded by Todd McKinnon, Frederic Kerrest. Tailscale was founded by Avery Pennarun, David Crawshaw, David Carney, Brad Fitzpatrick.
Which company has a longer operating history — Okta, Inc. or Tailscale?
Okta, 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 Okta vs Tailscale overview