--- title: 'Senior Web Experimentation Manager at Tailscale' canonical: 'https://feeny.ai/job/senior-web-experimentation-manager-tailscale-canada-v219v0jc1kfy' type: 'job' last_seen: '2026-10-20' --- # Senior Web Experimentation Manager at Tailscale - **Company:** Tailscale - **Location:** Canada - **Compensation:** $153k–$194k - **Work type:** remote - **Posted:** 2026-10-08 - **Last confirmed live:** 2026-10-20 - **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4739997005 ## Job description 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 Looking For - 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 ## Nice to Have - 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. CAN Pay Range $152,760—$194,300 CAD ## 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. ## About Tailscale ## Company Overview - **One-liner**: Tailscale provides a zero-trust identity-based connectivity platform that replaces legacy VPNs, SASE, and PAM to securely connect remote teams, multi-cloud environments, CI/CD pipelines, edge/IoT devices, and AI workloads. - **Entity Type**: Private (Series B) - **Headquarters**: Toronto, Canada (fully remote, with team members also in the United States and United Kingdom) - **Founded**: 2019 - **Founders**: Avery Pennarun (CEO), David Carney (Chief Strategy Officer), and Brad Fitzpatrick (creator of LiveJournal, Memcached, and OpenID) ## Core Business - **Primary industry/industries**: Secure connectivity, zero-trust networking, VPN replacement, infrastructure security - **Target customers**: B2B – from small businesses and open-source projects to mid-market and enterprise organizations (30,000+ businesses use Tailscale). Also serves developers, IT teams, and DevOps engineers. - **Mission or purpose statement**: “We want to help everyone create their own secure networks built around people and their connections. By making connectivity easier and more secure, we empower teams to build systems that scale, without scaling overhead.” ## Products & Services - **Tailscale (Core Platform)** – A zero-trust mesh overlay network that provides identity-based access to any resource (servers, containers, SaaS tools, cloud instances) without public exposure. Replaces legacy VPNs, bastion hosts, and complex firewall rules. Includes features like SSH, Kubernetes access, database connectivity, and Aperture for securing AI workloads. - **Tailscale Funnel** – Expose local services to the internet securely through Tailscale’s infrastructure. - **Tailscale Serve** – Allow specific devices on a tailnet to serve content publicly or privately. - **Tailscale SSH** – Manage SSH access with identity-based, auditable controls. - **Tailscale Aperture** – Secure access for AI/ML workloads and data pipelines. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed (private company) - **Key Metric (Funding)**: Total funding of approximately $105M across multiple rounds. Series A ($35M) led by CRV in 2021; Series B ($70M) led by Accel and Insight Partners in 2022. - **Key Metric (Customers)**: 30,000+ businesses use Tailscale. Headcount estimated at ~290 employees as of 2026. - **Notable Investors/Partners**: Accel, CRV, Insight Partners, Heavybit, Uncork Capital. Investors include Amit Kumar (Partner at Accel), Reid Christian (Partner at CRV), Joseph Ruscio (Partner at Heavybit), Rebecca Liu-Doyle (Director at Insight Partners), and Andy McLoughlin (Partner at Uncork). - **Growth Signals**: 25x headcount growth without dedicated IT resources for onboarding; 90% reduction in internal support requests; thousands of hours saved with fewer connectivity issues. Strong adoption in the AI era for securing workloads. ## Competitive Advantages - **Built on WireGuard**: Tailscale is built on the modern, audited, and high-performance WireGuard protocol (wireguard-go), with upstream contributions to the open-source project. - **Zero Trust by Design**: Identity-based access, end-to-end encryption, point-to-point connections (no central VPN server to bottleneck or inspect traffic). User privacy is a fundamental design principle. - **Simplicity & Speed**: “It has to just work” – installation takes minutes, configuration is minimal, and the platform is cross-platform and infrastructure-agnostic. - **Open Source Core**: The core client and server code are open source, and Tailscale offers a free plan for open-source projects, building trust and community. - **Small, Excellent Teams**: The company philosophy is “small is beautiful” – they believe small, excellent teams produce coherent, high-quality outcomes that large teams cannot replicate. ## Strategic Focus - **AI & Multi-Cloud Connectivity**: Tailscale is positioning itself as the secure connectivity platform for the AI era, with specific features (Aperture) for AI workloads. - **Expanding Enterprise Features**: Adding capabilities like Privileged Access Management (SSH, K8s, databases), granular access controls, and audit logging. - **Scaling the Business**: With 30,000+ businesses already onboard, the focus is on converting free/open-source users to paid plans and expanding into larger enterprise accounts. - **Global Hiring**: Actively hiring across engineering (Go, Infrastructure, Security, Mobile), customer success, sales, marketing, and operations in the US, Canada, and UK, with some roles in Singapore. ## Why Work Here - **Fully Remote & Flexible**: Tailscale is a fully remote company with team members across the US, Canada, and UK. Flexible working hours are core to the culture – employees are trusted to manage their time around their lives (family, appointments, etc.). - **Competitive Total Rewards**: Competitive salaries, generous equity incentive plans, group health benefits with no waiting periods, flexible sick days, and an employee assistance program. - **Work-Life Balance**: 26 weeks of paid parental leave, flexible paid vacation, 12 paid company holidays, and a full holiday closure from Dec 24 to Jan 1. - **Workspace Support**: Company-provided laptop (Mac/PC), monthly internet reimbursement, and a “build your own workstation” bonus. - **Engineering Culture**: Strong emphasis on open-source contribution, Go programming, and systems-level engineering. Many team members are active in the Go, NixOS, and SQLite communities. - **Inclusive & Diverse**: The company is committed to diversity and inclusion, with a team not bound by geography, lifestyle, or life stage. They provide accommodations throughout the interview process. - **Interview Process**: For technical roles: Recruiter Interview → Hiring Manager Interview → 2-3 Team Interviews → Technical Working Session → Offer. For non-technical roles: Recruiter → Hiring Manager → 2-3 Team Interviews → Offer. ## Sources 1. [tailscale.com](https://tailscale.com/) – Official website 2. [tailscale.com/company](https://tailscale.com/company) – About page, team, investors, guiding principles 3. [tailscale.com/careers](https://tailscale.com/careers) – Careers page, perks, benefits, culture 4. [job-boards.greenhouse.io/tailscale](https://job-boards.greenhouse.io/tailscale/jobs/4525230005) – Current job openings 5. [jobsbyculture.com](https://jobsbyculture.com/blog/working-at-tailscale-2026) – Employee culture review (2026, ~290 employees) ## Other roles at Tailscale - [Strategic Enterprise Account Executive](https://feeny.ai/job/strategic-enterprise-account-executive-tailscale-united-states-j72q76esbb7a) — United States - [Program Manager, EPD Operations](https://feeny.ai/job/program-manager-epd-operations-tailscale-united-states-vhxf8tc001tg) — United States - [Program Manager, EPD Operations](https://feeny.ai/job/program-manager-epd-operations-tailscale-canada-mp6zqbgcdha4) — Canada - [Senior Customer Account Executive](https://feeny.ai/job/senior-customer-account-executive-tailscale-vancouver-jwgp948yyayw) — Vancouver, Canada - [Senior Customer Account Executive](https://feeny.ai/job/senior-customer-account-executive-tailscale-toronto-4ck2hgsdjdry) — Toronto, Canada - [Infrastructure Engineer](https://feeny.ai/job/infrastructure-engineer-tailscale-united-states-8fvm5w9w0qtt) — United States - [Infrastructure Engineer](https://feeny.ai/job/infrastructure-engineer-tailscale-canada-4ewrr4nkwx0n) — Canada - [Senior Web Experimentation Manager](https://feeny.ai/job/senior-web-experimentation-manager-tailscale-united-states-6m7d0bt7z2fk) — United States - [Senior Solutions Engineer, Enterprise](https://feeny.ai/job/senior-solutions-engineer-enterprise-tailscale-united-states-dathcnv5kzrm) — United States - [Senior New Business Account Executive](https://feeny.ai/job/senior-new-business-account-executive-tailscale-toronto-zctksfgkrbrw) — Toronto, Canada