Teams at Tailscale

Lead resolution of high-severity post-sales escalations: investigate and reproduce complex networking and software issues, run customer calls, collect logs and evidence, create engineering-ready handoff packages, identify systemic patterns, and improve tooling and runbooks to raise Support's technical capability.

Partner with Account Executives to drive new commercial business by leading technical discovery, architecture design, demos and POCs. Guide complex deals, build scalable enablement and provide product/market feedback. Blend deep networking and security expertise with sales acumen to support quota attainment.

Lead the dataplane product vision and roadmap for Tailscale, owning connectivity features (WireGuard, relays, subnet routing, exit nodes, connectors), performance/reliability SLOs, regional relay capacity, operator tooling (console/CLI), and enterprise/regulatory deployments. Partner with engineering, GTM, and customers to drive production traffic commitments and improve connectivity across diverse NATs, OSes, carriers, and networks.