Product Manager, Tailscale
Growth
CA$175.5-296.1k
+ Equity
More information about location
A zero config VPN for building secure networks
Job no longer available
A zero config VPN for building secure networks
201-500 employees
Job no longer available
CA$175.5-296.1k
+ Equity
More information about location
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company 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
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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