Software Engineer, Strategic Projects

Tailscale

Software Engineer building prototypes and POCs for AI agents at Tailscale. Collaborating with customers for secure product integrations in a remote-first environment.

Posted 5/28/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSenior💰 $163,000 - $226,000 per yearWebsite

Tech Stack

Tools & technologies

GoOpen Source

About the role

Key responsibilities & impact

Build prototypes and POCs that showcase Tailscale for AI agents and tooling (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads).
Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products to enable secure customer connectivity.
Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations.
Rapidly iterate with input from colleagues and reference customers; turn customer conversations into shippable prototypes and reference designs.
Hold the production bar on prototypes that often graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code.
Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC.

Requirements

What you’ll need

Strong at rapid prototyping, explaining technical concepts, and working directly with customers in an exploratory, fast-paced environment.
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 how to wrap them in review and security practices that hold the production bar.
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.

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company—most of our teams work fully remotely.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Generous parental leave program from your first day.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Gorapid prototypingAPI integrationbasic networkingcoding agentsLLMssecurity practicesreview practicesreference architecturesdocumentation

Soft Skills

explaining technical conceptscustomer engagementindependent workadaptabilitycollaborationcommunicationproblem-solvingexploratory mindsetfast-paced environmentteamwork