Staff Product Designer 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 are looking for a Staff Product Designer to join the design team at Tailscale. You will primarily partner with the Network Features team, which owns one of the most technically complex and strategically important surfaces in the product: how traffic finds its destination, how networks are segmented and connected, and how operators control that behavior at scale. That spans a wide range. On the user-facing side, Admin users orchestrate their networks by configuring settings related to: subnet routing, exit nodes, App Connectors, Services, and DNS. On the infrastructure side, you’ll interface with topics like: traffic steering, high availability, DERP servers, and cloud networking primitives. These are not features with obvious consumer analogues. The users are network engineers, IT administrators, and developers building on top of Tailscale, and the problems they bring are genuinely hard to make simple. At the staff level, scope is not handed to you. You will define where design attention is needed across this space, lead discovery on problems that don't yet have clear answers, and shape product direction alongside your engineering and PM partners. A significant part of that work is translation: taking abstract technical systems and surfacing the design problems hidden inside them clearly enough that engineers, PMs, and stakeholders can align on what to solve and why. Diagramming, system mapping, and other artifacts that make complexity legible are tools you reach for naturally, not as documentation but as a way of driving shared understanding and unblocking decisions. Your influence will extend beyond your immediate projects, affecting how the broader design team approaches craft, process, and product thinking. You will report to the product design manager and work closely with a team of five product designers and one design researcher. Most of your time will be spent embedded with the Network Features team, with some involvement in wider design team or product initiatives. People who do well here are genuinely curious about networking and security, comfortable going deep on technically complex domains, and fluent working asynchronously with highly technical teammates. Key Responsibilities Define where design attention is needed across the network features product space and lead discovery on complex, ambiguous problems that often span multiple features or product areas. Translate abstract technical systems into clear problem frames, using diagramming, system mapping, and design artifacts to build shared understanding and drive alignment across engineering, product, and other stakeholders, Deliver design solutions end-to-end as needed, whether that means changes to a GUI, a CLI experience, or both, working closely with engineers through implementation and QA. Explore forward-looking design questions in spaces that do not yet have clear owners or established answers. Partner closely with engineering and PM counterparts to move from ambiguous problem statements to clear, well-reasoned solutions. Raise the bar for craft and quality across your team and contribute to how the broader design organization approaches process and product thinking. Translate insights from user research, behavioral data, and your own product knowledge into design direction. Bring AI tools into your workflow in practical ways, whether for research synthesis, rapid prototyping, or solution exploration, and develop a point of view on where AI-assisted experiences belong in technically complex products. What We Are Looking For 10+ years of product design experience, with meaningful time operating at the staff level or equivalent scope Strong portfolio demonstrating experience with technically sophisticated B2B or infrastructure products, and a track record of leading discovery on problems without waiting for scope to be defined A developed point of view on users and product direction, with evidence of using that perspective to influence roadmap and strategy across engineering and product teams Genuine interest in the networking and security space and comfort engaging with technically complex subject matter Strong written communication and an ability to articulate design decisions clearly to both technical and non-technical partners Ease working in a distributed, asynchronous environment with highly technical teammates Nice to Have Hands-on experience with Tailscale, or working familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routing Hands-on experience with cloud native deployment infrastructure (AWS, GCP, DigitalOcean, etc) Experience designing for developer or IT administrator audiences Data-informed design practice including behavioral analytics or experimentation Fluency with AI tools as part of your design workflow and curiosity about where AI-assisted experiences fit in technical products 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 $226,460—$282,740 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.