Apply networking expertise to complex customer escalations as a Customer Reliability Engineer at fully distributed Tailscale, working remotely across Canada.You will connect customers, Support, Customer Success, Product, and Engineering by investigating ambiguous technical problems. The role centers on deep debugging, evidence-based communication, and resolution or engineering handoff. Tailscale seeks someone with technical escalation experience, production networking knowledge, and robust systems troubleshooting skills.Key Responsibilities:
Own high-severity post-sales escalations through resolution or engineering handoffInvestigate difficult bugs, reproduce failures, and analyze logsLead customer calls and communicate theories clearly under pressurePrepare reproducible,



evidence-backed engineering handoff packagesTrack bugs and identify recurring issues for product improvementsRequirements:
Four or more years in technical support or escalation rolesHands-on TCP/IP, routing, DNS, firewall, NAT, and VPN experienceFamiliarity with WireGuard, UDP hole punching, and STUNAbility to debug Go, goroutines, locks, channels, and pprof profilesExperience with cloud infrastructure, Kubernetes, Linux, macOS, and WindowsBring networking, code-level debugging, and customer communication skills to resolve difficult technical issues for Tailscale customers.
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📌 Customer Reliability Engineer Networking (Winnipeg)
🏢 Tailscale
📍 Winnipeg