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Software Engineer, Strategic Projects

Tailscale· Strategic Projects
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Remote$163k - $226kFull-timePosted 2mo ago

About the role

AI-native software engineer role focused on prototyping-to-production for strategic initiatives (e.g., MCP gateways, LLM proxies, sandboxes, remote servers) at Tailscale, emphasizing security, reliability, observability, and collaboration with product-minded engineers and reference customers.

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 reliability and long-term supportability.
  • Find and close long-tail gaps, edge cases, regressions, flaky behavior, missing tests, undocumented operational knowledge that separate a prototype from a dependable product.
  • Establish and maintain 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 in North America.

Qualifications

  • 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 view on acceleration, limitations, and how to wrap them in review, testing, and security practices.
  • Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning production-ready work.
  • Comfort with the cadence of a strategy team at an early-stage startup: shifting priorities, short prototype-to-production timelines, and maintaining a high bar for what ships.
  • Thrive working independently in a remote environment.

Skills

Required:GoCoding with AI / LLM toolingProduction hardening & reliability

Benefits

  • Inclusive, flexible environment
  • Competitive total compensation package (base salary, equity, variable compensation for quota-based roles)
  • Comprehensive group benefits with no waiting period
  • Remote-first with occasional in-office collaboration noted in job description
  • Employer-funded retirement contributions (match up to 0.75% of eligible compensation)
  • Company retreats and team off-sites, in-person collaboration across multiple regions
  • Professional development support ($1500 USD annually)
  • Flexible paid time off
  • Build-your-own home office setup (laptop choice, internet reimbursement, $500 workstation stipend)
  • Paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing parents)
Last updated Sep 17, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
Company profileWebsite

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