Software Engineer, Strategic Projects (AI)

Location: Remote in Canada; light travel required, primarily for team and company offsites, with optional conferences or customer visits in North America.

Salary: CAD 218,420–302,840 annually, plus equity and comprehensive benefits.

Company

Tailscale builds secure connectivity software that interconnects people, devices, networks, and customer-facing products.

What you will do

• Partner with product-minded engineers to shape MCP gateways, LLM proxies, sandboxes, remote servers, and other emerging workloads for production.
• Harden prototypes through error handling, observability, testing, operational tooling, and reliability work.
• Own production, security, review, and operational standards for prototypes that become part of the product.
• Integrate Tailscale with reference customers for internal networking adoption and embedded customer-facing products.
• Identify and resolve edge cases, regressions, flaky behavior, missing tests, and undocumented operational knowledge.
• Establish practices for reviewing, testing, and securing agent-generated code.

Requirements

• Experience taking software from prototype to production, especially in startup-like environments.
• Strong production hardening, stabilization, maintenance, and debugging skills.
• Go experience, third-party API integration experience, and basic networking knowledge.
• Heavy daily use of coding agents such as Claude Code or Cursor and LLMs in engineering workflows.
• Ability to work independently and asynchronously in a fast-moving remote environment.
• Must be based in Canada and able to travel occasionally for team or company onsite events.

Nice to have

• Production operations experience with observability, on-call, incident response, performance, or reliability.
• Identity infrastructure and authentication experience, including OAuth, OIDC, SAML, SCIM, RBAC, ABAC, MFA, or passwordless authentication.
• Experience building LLM applications and agentic systems.
• Familiarity with Tailscale, multi-cloud or hybrid networking, and open-source communities.
• Python, Rust, or TypeScript experience.

Culture & Benefits

• Fully remote, flexible work environment with asynchronous collaboration and coworking support.
• Health, vision, dental, and other group benefits with no waiting period.
• Equity incentive plan, employer-funded retirement contributions, and paid time off.
• Annual professional development budget of USD 1,500, plus mentorship and coaching.
• Company laptop, monthly home internet reimbursement, and USD 500 for home office customization.
• Paid parental leave and opportunities for intentional in-person connection through retreats and offsites.

Hiring process

• AI-assisted tools may be used to screen and assess candidates; final hiring decisions are made by people.
• Accessible accommodations are available throughout the hiring process.