# Software Engineer, Strategic Projects

**Company:** [Tailscale](https://hotfix.jobs/companies/tailscale)
**Location:** Remote
**Role:** Fullstack Engineering
**Salary:** $163k – $226k/yr
**Experience:** 5+ years
**Skills:** Go, Python, Rust, TypeScript, OAuth, OIDC, SAML, SCIM, RBAC, Abac, LLMs, Coding Agents, Observability, Incident Response
**Posted:** 2026-06-25

> Software engineer on the Strategic Projects team building production-grade AI-native connectivity products from prototypes. Heavy Go, LLM/agent tooling, and production hardening focus.

## Job Description

## Key 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.

## Requirements
- Strong at hardening, stabilizing, and maintaining production software; detail-oriented work closing 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 engineering workflow, with a point of view on where they accelerate work, where they fail, and how to wrap them in review, testing, and security practices.
- 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.

## Nice to Have
- 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.

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