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. We're building a future for the Internet that's easy, sensible, and safe. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

We are seeking a motivated Customer Reliability Engineer to own our most complex, ambiguous customer escalations. You will bridge the gap between customer issues and engineering solutions, ensuring that technical problems are resolved or documented for engineering action.

Key Responsibilities

• Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff.
• Conduct deep-dive investigations, including log analysis and reproduction of difficult-to-isolate bugs.
• Communicate directly with customers on technical calls to build trust and investigate theories.
• Create comprehensive engineering handoff packages (reproducible cases, log evidence, version matrices, impact scope).
• Track confirmed bugs to ensure engineering retains full customer context.
• Monitor escalation patterns to drive product improvements, tooling, and internal runbooks.

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 (WireGuard, UDP hole punching, STUN).
• Code-level debugging capability: Go source, goroutines, pprof profiles, and network interface semantics.
• Strong systems administration skills across Linux, macOS, and Windows.
• Proficiency in Go, Python, and JSON.
• Experience with packet-level analysis.

What We Offer

• Competitive compensation package including base salary and equity.
• Comprehensive group benefits with no waiting period.
• Remote-first culture with annual company retreats and team off-sites.
• $1,500 USD annual professional development budget.
• $500 USD home office customization stipend + monthly internet reimbursement.
• Paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing parents).
• Employer-funded retirement contributions (matching up to 0.75% of eligible compensation).