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Software Engineer, Strategic Projects

Tailscale· Strategic Projects
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Hybrid (Canada)CA$218.4k - CA$302.8kfull-timePosted 2mo ago

About the role

Remote (Canada) role on the Strategic Projects team focused on turning prototypes into production-grade, secure, observable, and maintainable solutions. Works with AI-native tooling, coding agents, and customer-facing integrations to make Tailscale’s products production-ready and interoperable with customer systems.

Responsibilities

  • Partner with product-minded engineers from the start, shaping prototypes (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads) so the path to production is built in, not bolted on.
  • Co-own the journey from "works in a demo" to "stable in production": hardening, error handling, observability, and operational tooling.
  • Own the production bar on prototypes that graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code.
  • Work with reference customers to integrate Tailscale, both for internal adoption and for embedding into their products, with reliability, maintainability, and long-term supportability.
  • Find and close long-tail gaps, edge cases, regressions, flaky behavior, missing tests, undocumented operational knowledge, that separate a prototype from a dependable product.
  • Establish and maintain the review, testing, and security practices that let the team ship agent-generated code fast without compromising production bar.
  • Light travel required (<10%): primarily team and company onsites, with optional conferences or customer visits in North America.

Qualifications

  • Strong at hardening, stabilizing, and maintaining production software; detail-oriented, adept at closing edge cases and operational gaps.
  • 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 engineering workflow, with ability to wrap them in review, testing, and security practices that hold production bar.
  • Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning production-worthy work.
  • Comfort with the cadence of an early-startup strategy team: shifting priorities, short prototype-to-production timelines, high ship bar.
  • Thrives working independently in a remote environment.

Skills

Required:GoThird-party API integrationNetworking basicsCoding agents / LLM toolingProduction software hardening

Benefits

  • An inclusive, flexible environment
  • Competitive total compensation package including base salary and equity
  • Comprehensive group benefits with no waiting period
  • Remote first company with some in-office collaboration as noted
  • Employer-funded retirement contributions (match up to 0.75% of eligible compensation)
  • Annual company retreat and team off-sites
  • Professional development stipend ($1500 USD annually)
  • Paid time off and flexible time off program
  • Build-your-own home office setup (laptop, home internet reimbursement, $500 USD for workstation)
  • Paid parental leave with top-ups (20 weeks birthing, 16 weeks non-birthing)
Last updated Sep 17, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
Company profileWebsite

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