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Product Manager

2 weeks ago

Remote Canada Sanity Full time

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 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. 

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. 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.

Key Responsibilities

  • 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.

What We Are Looking For

  • 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

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 Ranges

$175,540 - $296,140 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/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
  • 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. 

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