Windows Engineer Remote (Canada)

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About Tailscale

Tailscale is making safe 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

We’re seeking a talented and motivated full-time Software Engineer to join our growing team. You will work as part of the engineering team to:

• Develop the Tailscale product, contributing to client code and backend services. The client code is a mix of C#, XAML, and Go. Prior Go expertise is not a requirement.
• Bring a special focus on our Windows platform, building and maintaining our Windows client using the modern WinUI/Windows App SDK stack, while contributing to common code that supports macOS, mobile, and other core client platforms.

Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.

Key Responsibilities

• Work with engineers on a native Windows desktop client using Windows App SDK, WinUI, C#, XAML and Go
• Implement support for the latest Windows platform features while maintaining compatibility with a subset of older versions
• Develop and optimize product features on Windows, with a focus on UI components and platform integration
• Develop and maintain unit and integration tests using Microsoft Testing Platform v2 and xUnit
• Contribute to common, cross-platform Tailscale code

What We Are Looking For

• Four or more years of experience in software development
• Strong understanding of software development principles, capabilities, and limitations of the Windows platform
• Proficiency in C# and modern native UI frameworks (WinUI/UWP/WPF)
• Experience with general networking concepts - DNS, VPNs, IP Networking, routing, etc.
• Excellent written and verbal communication skills
• Ability to give and process constructive feedback, as well as work independently
• Flexibility to adjust to the dynamic nature of a startup

Nice to Have

• Experience with WinUI 3 and Windows App SDK
• Experience developing native Windows applications and services
• Familiarity with Windows networking stack and Windows Filtering Platform
• Familiarity with Windows security model, session isolation, access tokens and related concepts
• Proficiency in Go

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

$191,620 - $239,860 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 retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• 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 Kingdom, Singapore.
• 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top‑ups (20 weeks for birthing parents, 16 weeks for non‑birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit .