Software Engineer, Strategic Projects

Key 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 (VPN replacement with identity-aware networking) and for embedding into their products, with particular attention to reliability, maintainability, and long-term supportability.
• Find and close the 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 the production bar.

Requirements

• Strong at hardening, stabilizing, and maintaining production software; detail-oriented work closing long tail of bugs, 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 a point of view on where they accelerate work, where they fail, and how to wrap them in review, testing, and security practices.
• Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning the work of getting something solid into production.
• Comfort with the cadence of a strategy team at an early-ish startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.
• Thrive working independently in a remote environment.

Nice to Have

• Experience operating production services: observability, on-call, incident response, performance and reliability work.
• Validating prototype code for production use alongside security teams.
• Identity infrastructure: IdP platforms, identity sync/provisioning, directory services; authentication protocols (OAuth, OIDC, SAML, SCIM); access control models (RBAC/ABAC), session management, MFA, passwordless auth.
• Building applications on top of LLMs and agentic systems (not just using them as dev tools).
• Familiarity with Tailscale itself and with networking challenges in multi-cloud and hybrid deployments.
• Open source community participation; experience producing publicly-visible artifacts (blog posts, talks, reference implementations).
• Python, Rust, and/or TypeScript.