Software Engineer, Strategic Projects

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 demo 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.
• Find and close edge cases, regressions, flaky behavior, missing tests, and undocumented operational gaps.
• Establish and maintain review, testing, and security practices that enable fast, safe delivery of agent-generated code.
• Travel less than 10%, primarily for team and company offsites, 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.
• Go experience is required.
• Experience integrating third-party APIs and basic networking knowledge.
• Heavy daily use of coding agents such as Claude Code or Cursor, and LLMs in engineering workflows.
• Ability to evaluate where coding agents accelerate work or fail, and to apply review, testing, and security practices that preserve production quality.
• 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 Have

• Experience operating production services, including observability, on-call, incident response, performance, and reliability.
• Experience validating prototype code for production use with security teams.
• Identity infrastructure experience, including IdP platforms, identity sync and provisioning, and directory services.
• Knowledge of OAuth, OIDC, SAML, SCIM, RBAC, ABAC, session management, MFA, or passwordless authentication.
• Experience building applications on LLMs and agentic systems.
• Familiarity with Tailscale and networking challenges in multicloud and hybrid deployments.
• Open source participation or experience producing public artifacts such as blog posts, talks, or reference implementations.
• Python, Rust, or TypeScript experience.

Compensation and Benefits

• Base salary range of $163,000–$226,000 USD.
• Equity incentive plan and variable commission for quota-based roles.
• Health, vision, dental, and other comprehensive group 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 equal to 0.75% of eligible compensation.
• Virtual and in-person social events and opportunities to connect with colleagues in person.