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.
We're hiring a Product Manager to own what it's like to build a Tailscale-native application — software with Tailscale connectivity and identity built in from the start.
You'd own the original front door to that world: TSNet, the Go library that puts a Tailscale node inside an application in a few lines of code; tailscale-rs, our new Rust-based SDK family (including C++, Python, and Elixir); the tailscale CLI powering scripting, automation, and CI; and the core Tailscale client library.
Products already get built this way, inside and outside Tailscale. Aperture, our AI connectivity gateway, and Tailscale PAM run on these primitives. So do LM Studio, NVIDIA, and Namespace.co, who embed Tailscale directly into their applications to give their users secure remote access, reach into customer networks safely, and bridge cloud environments without VPN gymnastics. One of those teams went from zero to a working embedded integration in hours. Your job is to make that the normal outcome for thousands of more applications.
Today this experience is engineering-led and the developer journey is uneven. The API is powerful, but the on-ramp from "I read a blog post" to "Tailscale is running inside my product" has real friction: auth key handling, onboarding flows designed for humans instead of embedded apps, docs and examples that don't yet tell a coherent story. You'll own that journey end to end and define, concretely, what it means to build a Tailscale-native application including the golden paths, the reference patterns, the APIs, and the developer experience that makes people say "wait, that's all it took?"
You'll report to Ross Kukulinski, VP Product, and work closely with the Rust, Golang, and Clients engineering teams, plus the internal product teams and external partners building Tailscale-Native Applications.
Key Responsibilities- Own the roadmap for the native apps experience: TSNet, tailscale-rs, and the tailscale CLI
- Define what "Tailscale-native application" means — the reference architectures, golden paths, and embedding patterns, packaged as docs, examples, and sample apps developers can build from
- Own the developer experience end to end: the on-ramp from blog post to running embedded node, API ergonomics, error messages, docs that work, examples that compile, and upgrade paths that don't burn early adopters
- Set the Rust SDK family strategy: which TSNet capabilities to port, which to skip, in what order, and how to position the library to developers.
- Treat the CLI as a product in its own right: scripting ergonomics, output conventions, automation surfaces, and the experience for platform and SRE teams running tailscale in CI and infrastructure-as-code
- Run the internal dogfood loop. Aperture and Tailscale PAM are built on these primitives; make those teams your most demanding customers and turn their friction into roadmap.
- Partner with GTM and Customer Success on embedding deals — AI platforms, developer tools, and infrastructure software shipping Tailscale inside their products — and let what you learn set priorities
- Engage developers where they live (GitHub issues, Discord, office hours) and build a coherent picture of what embedded developers need
- 6+ years in product management, or a software engineering background moving into product, with real time spent on a developer-facing product: an SDK, API, CLI, library, or developer tool
- You've shipped developer-facing features that developers used in production, and lived with the consequences of your design choices — naming, defaults, error behavior, versioning
- You can read Go and/or Rust and hold a credible technical conversation about API and SDK design
- You have taste in developer experience: opinions about API ergonomics, docs, error messages, and getting-started flows, with examples to back them up
- You do customer research the way developer products require it — reading GitHub issues, lurking in Discord, running office hours, and finding the pattern in the noise
- You turn ambiguous scope into shipped increments, close the loop after launch, and keep teams informed along the way
- Hands-on Go or Rust experience — you've built something real, even as a side project
- Time at a developer platform company with a strong SDK motion (e.g. Stripe, Twilio, Auth0, Vercel, Supabase, HashiCorp)
- Open-source community experience: contributor experience, issue triage, balancing commercial priorities with community needs
- Enough networking, zero-trust, or VPN familiarity to understand what embedding Tailscale does for a developer
- Experience designing CLIs or scripting surfaces for platform and SRE teams
- Public technical writing, talks, OSS contributions, or developer-tooling side projects
- LLMs and coding agents as part of your daily product workflow
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.
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.
- 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.
Tailscale Toronto, Ontario, CAN Office
Toronto, ON, Canada
