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Product Manager

Tailscaleabout 1 month ago
Remote
Canada
CA$124,987 - CA$210,855/yearly
Senior Level

Top Benefits

Flexible working hours
Competitive pay, stock options, 401(k)
Medical, dental, vision coverage

About the role

Who you are

  • This role is ideal for senior PMs with experience in growth, activation, or onboarding at product-led SaaS companies with technical products like dev tools, cloud infrastructure, etc
  • Required: 7+ years in a product role, with significant experience in growth, onboarding, or activation at a product-led SaaS company
  • Required: Strong understanding of (or eagerness to develop a strong understanding of) Tailscale’s product and customer base—you may already be a Tailscale user, or have significant experience working on a technical, developer-focused product
  • Required: Hands-on experience running A/B tests and product experiments, with the ability to interpret both quantitative and qualitative results
  • Required: Experience with data analytics tools (e.g. SQL, Looker, Snowflake) and comfort working with data teams to generate insights
  • Excellent communication skills, with a track record of aligning cross-functional stakeholders and translating insights into action
  • Strong product taste and empathy for users; you care as much about the quality of the experience as you do about the business outcomes
  • Prior experience working on developer tools, infrastructure products, or security-focused SaaS
  • Familiarity with lifecycle marketing, onboarding journeys, and funnel optimization outside the product

What the job involves

  • We’re looking for a data-driven, experimentation-minded Product Manager to join the team at Tailscale, focusing on product-led growth
  • In this role, you’ll own the onboarding and activation experience across all user types—personal, enterprise trial, and self-serve—and shape how users discover, adopt, and expand their use of Tailscale
  • You’ll report directly to the Head of Product and collaborate with peers across Product, Engineering, Design, Data, and Marketing
  • This is a strategic role where you’ll set the vision for growth at Tailscale and directly influence the company’s long-term trajectory
  • Success in this role requires a strong understanding of Tailscale’s product and its diverse use cases. You may already be a Tailscale user, or you’ll quickly become one
  • You’ll develop deep product fluency and use that knowledge to design growth initiatives that feel authentic, valuable, and aligned with how our customers—from individuals to enterprises—experience the product
  • Your initial focus will be on building seamless onboarding experiences that drive activation and early retention
  • You’ll design and run experiments that optimize conversion from trial to paid, working closely with lifecycle marketing to align in-product experiences with out-of-product touchpoints like email and campaigns
  • Over time, you’ll expand your scope to include in-product education, helping users discover new and underutilized features that match their needs, driving deeper adoption and expansion within both self-serve and enterprise accounts
  • At Tailscale, we believe that growth features shouldn’t feel bolted on or disruptive, but instead should guide and delight users as they get more value out of the product
  • This role is more than building in-product tours and popups! You’ll blend a rigorous, data-informed mindset with strong product taste to design experiences that are both effective and user-friendly
  • You’ll have structured mentorship from our Head of Product while also serving as a strategic thought partner across the product org, ensuring that growth experimentation is embedded into how Tailscale builds and scales
  • Partner with UXR and Data to conduct qualitative and quantitative research, translating insights into a clear growth roadmap
  • Design and run in-product experiments to drive conversion from trial to paid and other key business metrics, in close collaboration with lifecycle marketing for out-of-product touches
  • Build in-product education experiences that surface new and underutilized features, helping users expand their usage and get more value from Tailscale
  • Develop a deep understanding of Tailscale’s product, use cases, and customer segments, applying this knowledge to design growth initiatives that feel authentic and valuable
  • Collaborate with other product managers to ensure growth experiments are well-instrumented and respectful of core product workflows, coordinating experiment design when overlaps occur
  • Define and track success metrics for growth initiatives, balancing business impact with user experience

Benefits

  • Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
  • Competitive compensation, stock options and 401(k) (for United States-based employees)
  • Comprehensive medical/dental/vision benefits, and more
  • 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
  • An allowance for equipment to help you personalize your workspace

About Tailscale

Software Development
51-200

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