Software Engineer, Strategic Projects - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices. We're building a future for the Internet that's easy, sensible, and safe. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

Join our Strategic Projects team, reporting to the Engineering Manager and the Chief Strategy Officer. This team demonstrates why Tailscale should be the default connectivity substrate for internal infrastructure and customer-facing products.

This is an AI-native team. We use coding agents heavily as a force multiplier and expect every engineer to be a power user. We move fast from idea to prototype, and we are looking for engineers energized by the path from prototype to dependable, production-grade product.

Key Responsibilities

• Partner with product-minded engineers to shape prototypes (MCP gateways, LLM proxies, sandboxes) so the path to production is built in.
• 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.
• Work with reference customers to integrate Tailscale, focusing on reliability, maintainability, and long-term supportability.
• Close the long-tail gaps, edge cases, and regressions that separate a prototype from a dependable product.
• Establish review, testing, and security practices for agent-generated code.
• Light travel required (<10%) for team onsites and customer visits.

What We Are Looking For

• Strong experience hardening, stabilizing, and maintaining production software.
• Go experience is a must; comfort integrating third-party APIs and basic networking.
• Heavy daily use of coding agents (Claude Code, Cursor) and LLMs in your engineering workflow.
• Ability to thrive working independently in a remote environment.
• Comfort with the cadence of a strategy team where priorities shift with market signal.

Nice to Have

• Experience operating production services (observability, on-call, incident response).
• Experience with identity infrastructure (OAuth, OIDC, SAML, SCIM, RBAC).
• Experience building applications on top of LLMs and agentic systems.
• Familiarity with Tailscale and multi-cloud/hybrid networking.
• Proficiency in Python, Rust, or TypeScript.

What We Offer

• Competitive total compensation (base salary + equity).
• Comprehensive group benefits with no waiting period.
• Remote-first culture with home office stipend and internet reimbursement.
• Employer-funded retirement contributions.
• $1,500 USD annual professional development budget.
• Paid parental leave (20 weeks birthing / 16 weeks non-birthing).
• Flexible, paid time off.