Job Overview
Location
Remote (Canada)
Job Type
Full-time
Category
Product Designer
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • Senior Product Designer at Tailscale Inc., responsible for shaping the user experience of a secure networking platform used by IT administrators, DevOps engineers, and security professionals worldwide.
- • Day-to-day responsibilities include owning end-to-end design for ambiguous problems, collaborating closely with engineers and product managers to turn fuzzy concepts into shippable solutions, delivering designs across GUI and CLI surfaces, seeking and integrating feedback iteratively, taking initiative to improve collaboration and clarity, understanding broader product implications of design decisions, and leveraging AI tools to accelerate research and idea validation.
- • Tailscale is a fully remote, fast-growing company founded in 2019 and backed by top-tier investors including Accel, CRV, and Insight. The design team is small but impactful, operating in a high-autonomy environment where curiosity, technical comfort, and self-direction are valued. The company’s mission is to rebuild the Internet to be easy, sensible, and safe by making secure device interconnection simple for users of all scales.
- • In this role, you will deepen your expertise in designing for technical B2B audiences, strengthen your ability to lead discovery without clear briefs, enhance your cross-functional collaboration with engineers and PMs, refine your skills in writing and communicating design decisions clearly, and grow your impact in a distributed, high-trust culture that values initiative and craftsmanship.
🎯 Requirements
- • 5+ years of product design experience with a portfolio demonstrating end-to-end ownership of complex work
- • Experience with technically sophisticated B2B or infrastructure products, comfortable leading discovery in deep domains
- • Strong point of view on users and product quality, with confidence to act on it
- • Ability to work effectively alongside engineers and PMs who prioritize how things actually work
- • Clear, direct writing skills to explain design decisions to both technical and non-technical audiences
- • Self-directed workload management, adept at shifting priorities without needing external direction
- • Experience working successfully in distributed, asynchronous environments
🏖️ Benefits
- • Inclusive, flexible remote-first environment supporting authentic self-expression and work-life integration
- • Competitive total compensation including base salary, equity, and variable commission (for quota-based roles)
- • Comprehensive group benefits with no waiting period covering health, vision, dental, and more for employees and families
- • $1,500 USD annual professional development stipend plus access to mentorship, coaching, and internal promotion opportunities
- • Build-your-own home office setup: company-owned laptop (Mac or PC), monthly internet reimbursement, and $1,000 USD for workstation customization
- • Generous parental leave program with top-ups available from day one for up to 26 weeks
- • Paid time off supporting life events like moving or travel, plus opportunities for in-person connection via company retreats and team off-sites
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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