Customer Reliability Engineer - Tailscale

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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

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 a fully-documented handoff that engineering can act on without delay.

Key Responsibilities

• Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff.
• Conduct deep-dive investigations and reproduction of difficult-to-isolate bugs.
• Lead customer calls, pull logs, and communicate technical theories clearly.
• Build engineering handoff packages: reproducible cases, log evidence, version matrices, and impact scope.
• Monitor for patterns across escalations to translate findings into product improvements, tooling, and runbooks.
• Partner with Support, CSE, and Product/Engineering teams.

What We Are Looking For

• 4+ years in a technical support or escalation role at a SaaS or infrastructure company.
• Hands-on networking experience: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers.
• Deep familiarity with overlay networking concepts (WireGuard, UDP hole punching, STUN).
• Code-level debugging capability: Go source, goroutines, locks, channels, and pprof profiles.
• Proficiency with infrastructure concepts: cloud IaaS, CI/CD, containerization, and Kubernetes.
• Strong systems administration skills across Linux, macOS, and Windows.
• Experience with packet-level analysis and scripting (Go, Python, JSON).
• Strong technical storytelling skills to distill complex issues for various stakeholders.

What We Offer

• Competitive total compensation (base salary + equity).
• Comprehensive group benefits with no waiting period.
• Remote-first culture with annual retreats and team off-sites.
• $1,500 USD annual professional development budget.
• Employer-funded retirement contributions (up to 0.75% match).
• Flexible PTO and paid parental leave (20 weeks birthing / 16 weeks non-birthing).
• Home office setup: company laptop, monthly internet reimbursement, and $500 workstation stipend.