Software Engineer, Strategic Projects

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. The Software Engineer for Strategic Projects will join a team focused on showcasing Tailscale's capabilities for AI agents and tooling, working directly with customers to integrate products and produce demonstrative artifacts.

Responsibilities:

• Build prototypes and POCs that showcase Tailscale for AI agents and tooling (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads)
• Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products to enable secure customer connectivity
• Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations
• Rapidly iterate with input from colleagues and reference customers; turn customer conversations into shippable prototypes and reference designs
• Hold the production bar on prototypes that often graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code
• Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC

Requirements:

• Strong at rapid prototyping, explaining technical concepts, and working directly with customers in an exploratory, fast-paced environment
• 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 your engineering workflow, with a point of view on where they accelerate work, where they fail, and how to wrap them in review and security practices that hold the production bar
• 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
• Building applications on top of LLMs and agentic systems (not just using them as dev tools)
• 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
• Validating prototype code for production use alongside security teams
• 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