Software Engineer, Strategic Projects

Tailscale

Software Engineer developing prototypes and POCs for Tailscale's AI initiatives. Collaborating with customers to integrate Tailscale's solutions for AI and identity-aware networking.

Posted 5/28/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 CA$218,420 - CA$302,840 per yearWebsite

Tech Stack

Tools & technologies

GoOpen Source

About the role

Key responsibilities & impact

Build prototypes and POCs that showcase Tailscale for AI agents and tooling.
Work with reference customers to integrate Tailscale, both for internal adoption and for embedding into their products.
Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations.
Rapidly iterate with input from colleagues and reference customers.
Hold the production bar on prototypes that often graduate into Tailscale's product surface area.
Light travel required (~10-15%).

Requirements

What you’ll need

Strong at rapid prototyping, explaining technical concepts, and working directly with customers in an exploratory, fast-paced environment.
Go experience is a must; comfort integrating third-party APIs; basic networking.
Heavy daily use of coding agents (Claude Code, Cursor, or similar) and LLMs in your engineering workflow.
Comfort with the cadence of a strategy team at an early-ish startup.
Thrive working independently in a remote environment.

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company—most of our teams work fully remotely.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Generous parental leave program from your first day.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Gorapid prototypingthird-party API integrationbasic networkingcoding agentsLLMs

Soft Skills

explaining technical conceptscustomer engagementindependent workadaptabilitycollaboration