About the role

Software Engineer turning Tailscale’s AI connectivity prototypes into secure, reliable production products. Partnering with engineers and reference customers on integrations, operational readiness, and agent-generated code practices.

Responsibilities

Partner with product-minded engineers from the start to shape prototypes such as MCP gateways, LLM proxies, sandboxes, and remote servers for production readiness
Co-own the transition from demos to stable production through hardening, error handling, observability, and operational tooling
Own the production bar for prototypes entering Tailscale's product surface, including security and review practices around agent-generated code
Work directly with reference customers on Tailscale integrations for internal adoption and product embedding
Identify and close edge cases, regressions, flaky behavior, missing tests, and undocumented operational gaps
Establish and maintain review, testing, and security practices for rapidly shipping agent-generated code
Travel less than 10%, primarily for team and company onsites, with optional conferences or customer visits in North America

Experience taking software from prototype to production in startup-like environments
Strong ability to harden, stabilize, and maintain production software
Go experience is required
Comfort integrating third-party APIs
Basic networking knowledge
Heavy daily use of coding agents such as Claude Code or Cursor and LLMs in the engineering workflow
Ability to establish review, testing, and security practices for agent-generated code
Comfort collaborating with exploratory, product-minded engineers
Comfort with rapidly shifting priorities and short prototype-to-production timelines
Ability to work independently in a remote environment
Nice to have: production service operations, observability, on-call, incident response, performance and reliability work
Nice to have: security validation of prototype code
Nice to have: identity infrastructure, IdP platforms, identity sync/provisioning, directory services, OAuth, OIDC, SAML, SCIM, RBAC/ABAC, session management, MFA, and passwordless authentication
Nice to have: applications built on LLMs and agentic systems
Nice to have: Tailscale and multi-cloud or hybrid networking familiarity
Nice to have: open source participation and publicly visible technical artifacts
Nice to have: Python, Rust, and/or TypeScript

Equity incentive plan
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family
Flexible remote-first work environment
Corporate co-working program
Employer-funded retirement contributions matching contributions dollar-for-dollar, up to 0.75% of eligible compensation
Annual company retreat and team off-sites
$1500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop, with choice of Mac or PC
Monthly home internet reimbursement
$500 USD workstation customization allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
Inclusive and accessible hiring process with accommodations available