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About Tailscale

Tailscale is making protected connection effortless 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.

About the Role The Product Design team at Tailscale is looking for an experienced Designer to join our dedicated Product Growth team. You will be the second designer on an existing cross-functional team and work to propel initiatives around activation, onboarding, monetization, user expansion, and the referral flywheel.

Working closely with Product, UX Research, and Engineering, this role will focus on delivering minimum-viable solutions intended to test a hypothesis. We’re looking for someone who enjoys the cadence of regular delivery, learning from experiments, and upholding a high craft bar.

This role will work closely with an experienced Product Designer within the Growth space and will report to the Product Design Manager.

Key Responsibilities

Draft & propose product changes that intend to move the needle on existing growth initiatives.





Participate in the experimentation lifecycle, learning from research and iterating based on feedback.

Contribute to a backlog of experiment ideas, generating multiple ways to address friction areas and influence user behavior through interaction design and prototyping.

Understand what our users are trying to do and advocate for product changes that support their best interests.

Uphold a high quality standard for what ships, balancing the need for experimentation with a high bar for permanent changes.

Partner with your PM, researcher, fellow designer, and engineers to define problems, define experiment goals as they relate to solutions proposed, and measure impact through experimentation.

What We Are Looking For

3-5+ years of product design experience, ideally with time spent on onboarding, growth, or monetization work

Hands-on experience with common growth tooling and approaches such as A/B testing and behavioral analytics tooling (Amplitude, Pendo, etc.)

Experience with self-serve, product-led SaaS business motions

Comfort working with experiment results and interpreting findings that will guide design decisions

Skilled at balancing speed and quality of deliverable designs

Experience and skill working in distributed, async environments

Nice to Have

Hands-on experience with Tailscale,



or working familiarity with networking concepts such as DNS, VPNs, or traffic routing

Experience and opinion on thoughtful LLM tool usage within the design workflow, especially for prototyping and user testing

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

$163,480 - $245,220 CAD

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.

Employer-funded retirement contributions.

Tailscale will match your r

📌 Product Designer (Winnipeg)
🏢 Tailscale
📍 Winnipeg