Customer Reliability Engineer

Tailscale delivers software that securely interconnects people and their devices, making network access safe and effortless. The Customer Reliability Engineer owns complex customer escalations, investigates difficult technical issues, and either resolves them or provides fully documented handoffs to engineering. The role partners with Customer Success, Support, Product, and Engineering to improve troubleshooting, tooling, and customer outcomes.

Responsibilities:

• Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs
• Get on calls with customers, pull logs, and communicate with the customer about leading theories
• Build engineering handoff packages that require minimal follow-up questions: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what's already been ruled out, and a proposed engineering team to own the fix
• File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context
• Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org
• Partner with Support, CSE, and Product/Eng, while staying within this team's scope

Requirements:

• 4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts
• A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues
• Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure
• Hands-on networking experience in production or homelab environments: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers
• Deep familiarity with overlay networking concepts — WireGuard, UDP hole punching, STUN — and comparable VPN/networking products
• Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics
• Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging
• Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows
• Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly
• Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders
• Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution
• Proficiency with programming/scripting in Go, Python, JSON
• Experience with packet-level analysis