Software Engineer, Strategic Projects
Build and productionize emerging connectivity and AI-focused software, partnering with product-minded engineers and reference customers. The role emphasizes Go, production hardening, observability, security, testing, and reliable operation in an ambiguous remote startup environment.
About the job
Responsibilities
- Partner with product-minded engineers from the start, shaping prototypes such as MCP gateways, LLM proxies, sandboxes, and remote servers so the path to production is built in.
- Co-own the journey from prototype to stable production software through hardening, error handling, observability, and operational tooling.
- Own the production bar for prototypes that graduate into Tailscale's product surface area, including security and review practices for agent-generated code.
- Work with reference customers to integrate Tailscale for internal adoption and product embedding, emphasizing reliability, maintainability, and long-term supportability.
- Identify and close edge cases, regressions, flaky behavior, missing tests, and undocumented operational knowledge.
- Establish review, testing, and security practices that enable rapid delivery without compromising production quality.
- Travel less than 10%, primarily for team and company onsites, with optional conferences or customer visits in North America.
Requirements
- Experience taking software from prototype to production in startup-like environments.
- Strong ability to harden, stabilize, and maintain production software, including attention to bugs, edge cases, and operational gaps.
- Go experience.
- Experience integrating third-party APIs and basic networking knowledge.
- Heavy daily use of coding agents such as Claude Code or Cursor and LLMs in an engineering workflow.
- Ability to establish review, testing, and security practices around AI-generated code.
- Ability to collaborate closely with exploratory, product-minded engineers.
- Comfort with shifting priorities, short prototype-to-production timelines, and a high shipping bar.
- Ability to work independently in a remote environment.
Nice-to-haves
- Operating production services, including observability, on-call, incident response, performance, and reliability work.
- Validating prototype code for production use alongside security teams.
- Identity infrastructure, including IdP platforms, identity synchronization and provisioning, directory services, OAuth, OIDC, SAML, SCIM, RBAC, ABAC, session management, MFA, and passwordless authentication.
- Building applications on top of LLMs and agentic systems.
- Familiarity with Tailscale and networking challenges in multi-cloud and hybrid deployments.
- Open source community participation and publicly visible technical artifacts.
- Python, Rust, and/or TypeScript.
Compensation and Benefits
- Base salary range: $218,420–$302,840 CAD.
- Equity incentive plan and variable commission for quota-based roles.
- Comprehensive health, vision, and dental benefits with no waiting period.
- Remote-first, flexible work environment and corporate coworking program.
- Employer-funded retirement contributions, matching contributions dollar-for-dollar up to a maximum annual employer contribution of 0.75% of eligible compensation.
Skills
Go, Networking, Third-Party Apis, Claude Code, Cursor, LLMs, Observability, OAuth, OIDC, SAML, SCIM, Python, Rust, TypeScript
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