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Salary: USD 114,000 - 145,000 / 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'll 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 the role is coaching colleagues across web, design, and marketing on hypothesis quality, test design, and results interpretation. You'll own the complete experimentation lifecycle: from intake and prioritization through test design review, launch, results validation, and translating learnings into strategic recommendations.
Key responsibilities include:
- Owning the experimentation roadmap, prioritizing ideas against traffic, expected impact, and cost
- Setting and maintaining standards for all tests (sizing, statistical power, minimum detectable effect, guardrail metrics, decision rules)
- Reviewing test designs before launch and results before sharing to ensure rigor and trustworthiness
- Designing, building, and running the most consequential experiments yourself, particularly on pricing and homepage
- Maintaining the testing platform and measurement infrastructure with web development and analytics teams
- Serving as the source of truth for experimental learnings and translating results into web strategy recommendations
- Reporting program results to marketing leadership on learnings, shipped changes, and upcoming tests
- Coaching contributors on experimentation best practices
This role requires someone who has run an experimentation program at scale, not just individual experiments. You understand when testing is the right tool versus when a low-risk, reversible change can ship without one. You hold decision rules even when results are inconvenient and treat flat results as valuable information. Success means building a program the company trusts, results that withstand scrutiny, and learnings that drive product and strategy decisions.
Tailscale is a fully distributed, remote-first company founded in 2019, backed by top-tier VCs (Accel, CRV, Insight, Heavybit, Uncork Capital). The company builds a secure networking platform on WireGuard, serving teams from hobbyists to multinational corporations.
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, peeking risks, multiple comparisons
- Ability to evaluate test design and validity, and 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 the right tool versus shipping without testing
- Clear writing and communication skills for presenting 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 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 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.
