Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services

Telecommunication Services

51-250 (150)

Founded 2019

$115M raised

26 open positions

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Senior Product Designer

1 hour, 48 minutes ago

Canada

Full-time

Senior

Product Designer (UI/UX)

Design and User Experience

DNS Prototyping UI Design UX Design

Apply Now

Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services

51-250

Founded 2019

$115M raised

View All Jobs 26

Description

Own discovery and design for ambiguous product problems from early framing through delivery and QA.
Work closely with product managers and engineers to turn fuzzy problems into well-reasoned, shippable solutions.
Design across both GUI and CLI surfaces and stay involved through implementation, not just handoff.
Seek and apply feedback from peers, the team, and the manager throughout the design process.
Take initiative in collaboration and push for clarity even on projects you are not leading.
Understand the product areas you work on deeply enough to anticipate broader implications of design decisions.
Use AI tools to synthesize research, explore directions faster, and pressure-test ideas when helpful.

Requirements

5+ years of product design experience with a portfolio showing end-to-end ownership of complex work.
Experience with technically sophisticated B2B or infrastructure products.
Comfort leading discovery in a domain without waiting for a fully defined problem.
A strong point of view on users and product quality, with the confidence to act on it.
Ability to work effectively with engineers and product managers who care deeply about implementation details.
Clear, direct writing skills for explaining design decisions to both engineers and stakeholders.
Strong workload management and the ability to shift between projects as priorities change.
Experience working distributed and asynchronously.
Nice to have: Hands-on experience with Tailscale or familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routing.
Nice to have: Experience designing for developer or IT administrator audiences.
Nice to have: Data-informed design practice, including behavioral analytics or experimentation.
Nice to have: Fluency with AI tools in a design workflow and curiosity about AI-assisted experiences in technical products.

Benefits

Competitive total compensation package including base salary, equity, and variable commission for quota-based roles.
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and their families.
Remote-first work environment with flexibility to work from wherever you have Wi-Fi, plus access to virtual and in-person social events.
Corporate co-working program for use of WeWork or similar spaces near you.
$1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
Flexible paid time off to support work-life integration.
Home office setup support including a company-owned laptop, monthly home internet reimbursement, and $1,000 USD for workstation customization.
Generous parental leave top-ups for up to 26 weeks, available from the first day.

Interested in this position?

Apply directly on the company website

Apply Now

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