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 exists to show developers and organizations why Tailscale should be their default connectivity substrate. We are an AI-native team that uses coding agents as a force multiplier to ship high-quality, secure, and production-grade software.

We move fast from idea to prototype, and we are looking for engineers who are energized by the path from prototype to dependable product. You will work shoulder-to-shoulder with product-minded engineers to ensure our prototypes are stable, observable, maintainable, and ready for real customer load.

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).
• Own the production bar on prototypes that graduate into Tailscale's product surface area.
• Work with reference customers to integrate Tailscale for internal adoption and product embedding.
• 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 (<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 with third-party APIs and basic networking.
• Heavy daily use of coding agents (Claude Code, Cursor) and LLMs with a clear point of view on their application in production environments.
• Ability to thrive working independently in a remote, asynchronous environment.
• Comfort with the fast-paced, shifting priorities of a strategy team at an early-stage startup.

Nice to Have

• Experience with observability, on-call, and incident response.
• Knowledge of identity infrastructure (OAuth, OIDC, SAML, SCIM) and access control models.
• Experience building applications on top of LLMs and agentic systems.
• Familiarity with Tailscale and multi-cloud/hybrid networking challenges.
• 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 support for home office setup and internet reimbursement.
• $1,500 USD annual professional development budget.
• Paid parental leave program (20 weeks birthing / 16 weeks non-birthing).
• Employer-funded retirement contributions (up to 0.75% match).