About the role
About Tailscale Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. Job Description Join our Strategic Projects team, reporting to
the team's Engineering Manager and ultimately into our co-founder and Chief Strategy Officer. This team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative. This is an AI-native team. We use coding agents heavily as a force multiplier and expect every engineer to be a power user. Our customers demand a high bar on code quality, security, and operational rigour, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it. You will build prototypes and POCs, work directly with reference customers on integrations, and produce externally-visible artifacts (blog posts, reference repos, conference demos, customer integrations) that demonstrate how Tailscale's emerging platform solves real problems in AI infrastructure, agentic tooling, and identity-aware networking. Tailscale is fully remote, this team operates with significant ambiguity, and the shipping cadence is fast. Comfort working asynchronously and collaborating with highly technical customers is essential. Key
Responsibilities 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. What We Are Looking For Ideal candidates will have experience iteratively developing software in startup-like environments. We don't expect expertise with every aspect listed below. Let us know where you feel you have the most experience and where you'd like to keep developing. 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.