Customer Reliability Engineer

Summary

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a Customer Reliability Engineer to manage complex customer escalations and ensure effective communication between customers and engineering teams.

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

Skills

• 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/networking products
• Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics
• Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging
• Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows
• Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly
• Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders
• Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution
• Proficiency with programming/scripting in Go, Python, JSON
• Experience with packet-level analysis

Qualifications

Must Haves

• 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/networking products
• Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics
• Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging
• Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows
• Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly
• Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders
• Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution
• Proficiency with programming/scripting in Go, Python, JSON
• Experience with packet-level analysis

Benefits

• Base salary, an equity incentive plan and variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period (health, vision, dental, and more)
• Remote first company—most of our teams work fully remotely
• Employer-funded retirement contributions; match dollar-for-dollar up to a maximum annual employer contribution equal to 0.75% of your eligible compensation
• Attend our annual company retreat
• Participate in team off-sites
• Support intentional in-person connection through team travel and distributed collaboration
• Support for your personal and professional development (grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities)
• Paid time off and a healthy work-life integration (flexible, paid time off program)
• A build-your-own home office setup (company-owned laptop (Mac or PC); monthly home internet reimbursement; $500 USD to customize your workstation)
• Paid parental leave program (parental leave top-ups: 20 weeks for birthing parents, 16 weeks for non-birthing parents)