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Salary: CAD 152,760 - 194,300 / annual
Tailscale is seeking a Senior Web Experimentation Manager to own and scale the experimentation program across the company's highest-traffic website pages, including the homepage, pricing, use-case pages, and paid landing pages. This is a hands-on leadership role where you will set the experimentation roadmap, establish test design standards, and personally design and ship the highest-stakes experiments.
You will work cross-functionally with web strategy, web development, design, product marketing, and analytics teams. A key part of this role is coaching colleagues across web, design, and marketing on hypothesis quality, test design, and result interpretation. You'll be responsible for maintaining the integrity of the experimentation program—reviewing test designs before launch and results before they're shared to ensure every number reported can withstand scrutiny.
Key responsibilities include: owning the experimentation roadmap and prioritizing tests against traffic, expected impact, and cost; setting and maintaining standards for statistical rigor (sizing, power, minimum detectable effect, guardrail metrics, decision rules); designing and running the most consequential experiments yourself, particularly on pricing and homepage; ensuring the testing platform and measurement infrastructure work correctly; maintaining an experiment record as the source of truth; reporting program results and learnings to marketing leadership; and coaching contributors on experimentation best practices.
You'll demonstrate sound judgment about when experimentation is the right tool versus when a change is low-risk enough to ship without testing. Success means building a program the rest of the company trusts, producing results that hold up to scrutiny, and generating learnings that inform product and marketing strategy.
Tailscale is a fully distributed, remote-first company founded in 2019, backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. The company builds a secure networking platform on WireGuard that helps teams of all sizes protect networks, share access to internal tools, and more.
REQUIREMENTS:
- 6–9 years of experience in conversion optimization, web experimentation, growth marketing, or related field, including ownership of an experimentation program across multiple pages or products
- Deep experience with a testing platform (Optimizely, VWO, or comparable), including program-level setup and governance
- Strong command of experiment statistics: power and sample size, minimum detectable effect, false positive control, guardrail metrics, sample ratio mismatch, risks of peeking and multiple comparisons
- Ability to evaluate test design and validity; ability to explain plainly why a result should or shouldn't be trusted
- Comfort with HTML, CSS, and JavaScript to build and debug client-side variations
- Working proficiency in SQL and an analytics tool (GA4 or similar) to validate results independently
- Sound judgment about when experimentation is appropriate versus when to ship without testing
- Clear writing and communication skills; ability to present results and tradeoffs to senior stakeholders
- Experience coaching or mentoring others on experimentation (formal or informal)
- Comfort working in a remote-first, async environment
NICE TO HAVE:
- Experience experimenting on pricing pages or pages routing visitors between self-serve and sales-assisted paths
- Experience with B2B SaaS, developer tools, infrastructure, or cybersecurity products
- Experience with server-side or feature-flag testing, or Bayesian/sequential testing methods
- Experience migrating an experimentation program between testing platforms
- Familiarity with accessibility and web performance considerations in test builds
- Experience building an experiment library for other teams
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
