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 solid systems troubleshooting skills.

Key Responsibilities

Own high-severity post-sales escalations through resolution or engineering handoff

Investigate difficult bugs, reproduce failures, and analyze logs

Lead customer calls and communicate theories clearly under pressure

Prepare reproducible,



evidence-backed engineering handoff packages

Track bugs and identify recurring issues for product improvements

Requirements

Four or more years in technical support or escalation roles

Hands-on TCP/IP, routing, DNS, firewall, NAT, and VPN experience

Familiarity with WireGuard, UDP hole punching, and STUN

Ability to debug Go, goroutines, locks, channels, and pprof profiles

Experience with cloud infrastructure, Kubernetes, Linux, macOS, and Windows

Bring networking, code-level debugging, and customer communication skills to resolve difficult technical issues for Tailscale customers.

📌 Customer Reliability Engineer Networking (Winnipeg)
🏢 Tailscale
📍 Winnipeg