Note: The job is a remote job and is open to candidates in USA. Tailscale builds software that makes it easy to securely interconnect people and devices. The Strategic Projects team is seeking a Software Engineer to take AI and connectivity prototypes from concept to dependable production products, partnering with product-minded engineers and reference customers. The role focuses on production hardening, security, observability, testing, operational tooling, and customer integrations.
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 (<10%): primarily team and company onsites, with optional conferences or customer visits concentrated in North America
Skills
- Ideal candidates will have experience taking software from prototype to production in startup-like environments
- 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
- 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 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
- 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
- Light travel required (<10%): primarily team and company onsites, with optional conferences or customer visits concentrated in North America
Benefits
- An inclusive, flexible environment where you can be your authentic self.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family.
- Remote first company—most of our teams work fully remotely.
- Virtual and in-person social events.
- Corporate co-working program to visit WeWork or similar spaces near you.
- Annual company retreat and team off-sites.
- $1500 USD annually for professional development.
- Mentorship, coaching, and internal promotion opportunities.
- Flexible, paid time off program.
- A company-owned laptop (Mac or PC).
- Monthly home internet reimbursement.
- $500 USD to customize your workstation.
- Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Employer-funded retirement contributions: Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
Company Overview
Company H1B Sponsorship