Customer Reliability Engineer

About Tailscale Tailscale is making safe connection effortless 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. About the Role If you're passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We're seeking a motivated Customer Reliability Engineer to join our team. You'll take ownership of our most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious. You will work these issues to resolution or alternatively a fully-documented handoff that engineering can act on without delay. As a Customer Reliability Engineer, you'll partner closely with the Customer Success Team, Support Team, and Product/Engineering to close the gap between "customer has described a problem" and "engineering has what it needs to fix it." This role reports directly to the Customer Reliability Engineer Team Lead. Key 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. What We Are Looking For 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/