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Senior Web Experimentation Manager

Tailscale · Remote (Canada) · Remote

Pay: CAD 152,760 – 194,300 a year

Posted Oct 8, 2026

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Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role We're looking for a Senior Web Experimentation Manager to own the experimentation program across Tailscale's highest-traffic website pages, including the homepage, pricing, use-case pages, and paid landing pages. You'll set the roadmap, the test design standards, and the decision rules every experiment runs on, and you'll design and ship the highest-stakes tests yourself. You'll work closely with web strategy, web development, design, product marketing, and analytics partners, and you'll coach the people running tests alongside you. This role is for someone who has run an experimentation program, and not only experiments. You know when a test is the right tool and when a change is better shipped without one. You can hold a decision rule when a result is inconvenient, and you treat a flat result as information. Success means a program the rest of the company trusts, results that hold up to scrutiny, and learnings that change what we build next. Key Responsibilities Own the experimentation roadmap, from taking in ideas across the team to prioritizing them against traffic, expected impact, and cost. Set and maintain the standards every test runs on, including sizing, statistical power, minimum detectable effect, guardrail metrics, and the rules for shipping, iterating, or stopping a test. Review test designs before launch and results before they're shared, so every number we report is one we can stand behind. Design, build, and run the most consequential experiments yourself, particularly on pricing and the homepage. Own the health of our testing platform and measurement with web development and analytics, so tracking works and results reconcile with our analytics data. Maintain the experiment record as the source of truth for what our website has learned, and turn accumulated results into recommendations for web strategy. Report program results to marketing leadership: what we learned, what shipped, and what we're testing next. Coach contributors across web, design, and marketing on hypothesis quality, test design, and reading results correctly. What We Are…