Software Engineer, Strategic Projects

About the role

This team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative. This is an AI-native team. We use coding agents heavily as a force multiplier and expect every engineer to be a power user.

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.
• Light travel required (

Requirements

Experience taking software from prototype to production in startup-like environments. 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 especially how to wrap them in the review, testing, and security practices that hold the production bar. 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.

Qualifications

• Strong at hardening, stabilizing, and maintaining production software; you take satisfaction in detail-oriented work and in closing the long tail of bugs, edge cases, and operational gaps.
• 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.

Skills

• 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.

Benefits

Flexible remote work, full-time employment, comprehensive benefits, employer-funded retirement contributions, and a variety of professional development opportunities.

Pay

$163,000—$226,000 USD

Schedule

Full-time, remote-first