[Remote] Staff Product Designer

Note: The job is a remote job and is open to candidates in USA. Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a Staff Product Designer to partner with the Network Features team, focusing on translating complex technical systems into clear design solutions and driving alignment across stakeholders.ResponsibilitiesDefine 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 areasTranslate 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 stakeholdersDeliver 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 QAExplore forward-looking design questions in spaces that do not yet have clear owners or established answersPartner closely with engineering and PM counterparts to move from ambiguous problem statements to clear, well-reasoned solutionsRaise the bar for craft and quality across your team and contribute to how the broader design organization approaches process and product thinkingTranslate insights from user research, behavioral data, and your own product knowledge into design directionBring 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 productsSkills10+ years of product design experience, with meaningful time operating at the staff level or equivalent scopeStrong 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 definedA developed point of view on users and product direction, with evidence of using that perspective to influence roadmap and strategy across engineering and product teamsGenuine interest in the networking and security space and comfort engaging with technically complex subject matterStrong written communication and an ability to articulate design decisions clearly to both technical and non-technical partnersEase working in a distributed, asynchronous environment with highly technical teammatesHands-on experience with Tailscale, or working familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routingHands-on experience with cloud native deployment infrastructure (AWS, GCP, DigitalOcean, etc)Experience designing for developer or IT administrator audiencesData-informed design practice including behavioral analytics or experimentationFluency with AI tools as part of your design workflow and curiosity about where AI-assisted experiences fit in technical productsBenefitsAn inclusive, flexible environment where you can be your authentic self.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.Company OverviewTailscale is a software company that provides zero-configuration virtual private networks (VPNs) for secure connectivity. It was founded in 2019, and is headquartered in Toronto, Ontario, CAN, with a workforce of 201-500 employees. Its website is https://www.tailscale.com.