We encourage you to help us break that statistic!

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 protected, like it used to be.

We’re seeking a skilled and diligent full-time Software Engineer to join our growing team. Support and enable internal business units through shared engineering services and functionalities, building the tools and processes for those teams to succeed.

Build relationships with multiple stakeholders across the organization to understand and meet their needs with projects you'll own end to end.

Work directly with internal customer facing teams to empower their mission and take pride in making their day-to-day lives easier. Work with product engineering to extract the data needed to drive business decisions.

Identify and build improvements for Continuous Deployment

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

Work as part of a team of engineers to design, build, test, and document core software components.

Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations.

Experience with operating managed services in a cloud environment (preferably AWS)

Familiarity with networks (IP addressing, routing, etc.)





Most of the non-front-end portions of the system are developed in the Go programming language. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. CAN Pay Range$218,420—$273,360 CAD An inclusive, flexible environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).

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 .

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.

Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.

Support for your personal and professional development. 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. 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).

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.

📌 Network Engineer Cloud (Winnipeg)
🏢 Candidate
📍 Winnipeg