Senior Product Designer

🕒 May 8

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• Own discovery and design on problems that don't always come with a clear brief, from early framing through delivery and QA. • Work closely with engineers and PMs to move from a fuzzy problem to something well-reasoned and shippable. • Deliver across surfaces, GUI and CLI alike, and stay engaged through implementation, not just handoff. • Treat feedback as part of the work, not a checkpoint. Seek it out from peers, your team, and your manager, and use it to make the work better. • Take initiative in how you collaborate and push for clarity, even on projects you're not leading. • Understand the product areas you touch well enough to know when a decision has implications beyond the immediate problem. • Use AI tools where they actually help, synthesizing research, exploring directions faster, pressure-testing ideas.

🎯 Requirements

• 5+ years of product design experience, with a portfolio that shows you've owned complex work end-to-end, not just executed on it • Experience with technically sophisticated B2B or infrastructure products. You're comfortable going deep on a domain and know how to lead discovery without waiting for a problem to be handed to you • A real point of view on users and product quality, and the confidence to act on it • At ease working alongside engineers and PMs who care a lot about how things actually work • A clear, direct writer. You can explain a design decision to an engineer and a stakeholder without producing two different documents • You run your own workload well, can shift between projects as priorities change, and don't need someone else to tell you what matters • Experienced working distributed and async, and good at it.

🏖️ Benefits

• An 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.