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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.
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.
- 6–9 years of experience in conversion optimization, web experimentation, growth marketing, or a related field, including ownership of an experimentation program across multiple pages or products
- Deep experience with a testing platform such as Optimizely, VWO, or a comparable tool, including program-level setup and governance
- Strong command of experiment statistics, including power and sample size, minimum detectable effect, false positive control, guardrail metrics, sample ratio mismatch, and the risks of peeking and multiple comparisons
- The ability to evaluate a test's design and validity, and 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 yourself
- Working proficiency in SQL and an analytics tool such as GA4, enough to validate results independently of the testing platform
- Sound judgment about when an experiment is the right tool, and when a change is low-risk and reversible enough to ship without one
- Clear writing and communication, with the ability to present results and tradeoffs to senior stakeholders
- Experience coaching or mentoring others on experimentation, formally or informally
- Comfort working in a remote-first, async environment
- Experience experimenting on pricing pages, or on pages that route 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 with Bayesian or sequential testing methods
- Experience moving an experimentation program from one testing platform to another
- Familiarity with accessibility and web performance considerations in test builds
- Experience building an experiment library that other teams use
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.
What We Offer
- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
- Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
- Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
- A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Skills Required
- 6–9 years of experience in conversion optimization, web experimentation, growth marketing, or a related field, including ownership of an experimentation program across multiple pages or products
- Deep experience with a testing platform such as Optimizely, VWO, or a comparable tool, including program-level setup and governance
- Strong command of experiment statistics, including power, sample size, minimum detectable effect, false positive control, guardrail metrics, sample ratio mismatch, peeking risks, and multiple comparisons
- Ability to evaluate test design and validity and explain whether results should be trusted
- Comfort with HTML, CSS, and JavaScript to build and debug client-side variations
- Working proficiency in SQL and an analytics tool such as GA4
- Sound judgment about when experimentation is appropriate versus when a change should ship without a test
- Clear writing and communication skills, including presenting results and tradeoffs to senior stakeholders
- Experience coaching or mentoring others on experimentation
- Comfort working in a remote-first, asynchronous environment
- 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 or 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
Tailscale Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Tailscale and has not been reviewed or approved by Tailscale.
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Fair & Transparent Compensation — Pay is framed as market-competitive across functions and geographies, with compensation bands and ranges frequently described in concrete terms. Salary-range transparency is also emphasized through openly posted ranges and an “equitable total rewards” positioning.
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Leave & Time Off Breadth — Time off is positioned as flexible, with paid holidays and an extended year-end closure window highlighted. This breadth is presented as enabling meaningful disconnect time rather than narrowly defined PTO only.
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Parental & Family Support — Paid parental leave is described as substantial, including top-ups for an extended period. Family-inclusive health benefits with immediate eligibility are also positioned as supportive for dependents.
Tailscale Insights
What We Do
For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.
