Teams at Tailscale

Build and operate infrastructure and core software components supporting Tailscale’s product and internal teams. Responsibilities include improving observability, CI/CD, cloud infrastructure, managed services, Kubernetes operations, scalability, stability, and automation. The role includes incident response, customer support escalations, cross-functional collaboration, documentation, and end-to-end ownership of infrastructure projects in a fully remote startup environment.

Own Tailscale’s web experimentation program across high-traffic pages. Set the roadmap, testing standards, statistical decision rules, and platform governance; design and run high-impact pricing and homepage experiments; validate tracking and results; maintain the experiment knowledge base; report findings to marketing leadership; and coach teams on hypothesis quality, test design, and interpretation. The role partners with web, development, design, product marketing, and analytics in a remote-first environment.

Build and lead Tailscale’s internal AI enablement capabilities, including developer tools, workflows, coding-agent practices, evaluation processes, and safety guardrails. Partner with engineering and other teams to identify high-impact AI opportunities, drive adoption, measure productivity and quality outcomes, and communicate recommendations to leadership. The role requires hands-on software engineering, internal tooling, AI coding-tool expertise, strong communication, and comfort working independently amid ambiguity.