Web Strategy & Growth Manager at Tailscale in Canada

About Tailscale Tailscale is building the new Internet 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. Job Description We’re looking for a Web Strategy & Experimentation Manager to help shape and optimize the digital experience across our marketing website. This role sits at the intersection of web strategy, user experience, conversion optimization, and cross-functional execution. You’ll lead strategic web initiatives from planning through launch, partner closely with stakeholders across Marketing, Product Marketing, Brand, SEO, and Product, and own a high-velocity experimentation program focused on improving user engagement and increasing sign ups. This is an ideal role for someone who is equal parts strategist, operator, and optimizer. You know how to balance long-term website improvements with fast-moving experimentation, and you’re comfortable influencing priorities across a wide range of stakeholders. Key Responsibilities Web Strategy and Site Ownership Partner with stakeholders across Marketing, Product Marketing, Brand, SEO, Product, and Engineering to plan and execute web initiatives. Help shape the website roadmap based on business goals, user behavior, technical opportunities, and performance data. Identify opportunities to improve site structure, navigation, content discoverability, and user journeys. Lead and support large-scale web initiatives such as: Content migrations Site restructures New page launches CMS improvements Website refreshes and redesign efforts Audit existing website experiences and recommend improvements for usability, scalability, and conversion. Ensure projects are clearly scoped, documented, prioritized, and communicated across teams. Act as a strategic partner to stakeholders while balancing business needs, technical feasibility, and user experience. Experimentation and Growth Optimization Own the website experimentation program using tools like VWO. Build and maintain an experimentation roadmap aligned to business priorities and conversion goals. Develop hypotheses grounded in user behavior, analytics, qualitative feedback, and business context. Launch A/B tests, multivariate tests, personalization campaigns, and UX experiments focused on improving: Sign ups Conversion rates User engagement CTA performance Navigation flows Landing page performance Analyze experiment results and communicate insights, recommendations, and next steps to stakeholders. Partner with analytics and engineering teams to ensure accurate tracking, measurement, and reporting. Create a culture of evidence-based decision making through experimentation and iterative improvement. Cross-Functional Collaboration Work closely with: Web developers Designers SEO specialists Product marketers Content teams Growth marketers Analytics teams Translate business goals into actionable web strategies and experiment plans. Communicate timelines, tradeoffs, risks, and recommendations clearly to stakeholders. Help establish scalable processes for web requests, experimentation intake, prioritization, and reporting. What We Are Looking For 5+ years of experience in web strategy, growth marketing, web optimization, digital experience, or a related field Experience managing complex web projects with multiple stakeholders and moving priorities Strong understanding of conversion rate optimization (CRO) and experimentation methodologies Hands-on experience running A/B tests and experiments using tools like VWO, Optimizely, or similar platforms Experience working with CMS platforms and modern marketing websites Strong analytical mindset with experience using tools like GA4, Looker Studio, or other analytics platforms Ability to synthesize qualitative and quantitative data into actionable recommendations Strong communication and stakeholder management skills Highly organized with the ability to manage multiple projects simultaneously Comfortable operating independently and driving initiatives forward with minimal oversight 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 $127,300—$159,460 CAD 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! 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. 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, and the United Kingdom. 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 $1000 USD to customize your workstation to make it your own. Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. 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.