Senior Customer Support Engineer

About the role

Tailscale is seeking a dedicated Senior Customer Support Engineer to join our team. This role focuses on resolving intricate technical challenges and fostering strong relationships between our users and the engineering department. You will be instrumental in tackling complex customer issues, ensuring their swift and effective resolution.

Key facts

What you'll do

• Take charge of high-priority customer issues from initial report to final solution or a comprehensive handover to the engineering team.
• Conduct in-depth investigations and replicate difficult-to-diagnose software defects.
• Engage directly with customers, gather necessary diagnostic data, and communicate potential causes of issues.
• Prepare detailed documentation for engineering, including reproducible steps, log evidence, system configurations, impact assessments, and suggested resolution paths.
• Identify recurring problems across customer escalations to drive improvements in product, tooling, and internal documentation.
• Collaborate with Support, Customer Success, and Product/Engineering teams to bridge the gap between reported problems and their solutions.

Requirements

• Minimum of 4 years of experience in a technical support or escalation engineering capacity within a SaaS or infrastructure company, with a history of managing enterprise-level accounts.
• Proven ability to troubleshoot and resolve complex, ambiguous technical problems.
• Experience leading customer calls during critical situations, maintaining composure, building trust, and communicating clearly.
• Practical knowledge of networking fundamentals including TCP/IP, routing, DNS, firewalls, NAT, VPNs, and load balancers, gained through professional or personal projects.
• Familiarity with overlay networking concepts such as WireGuard, UDP hole punching, and STUN, as well as comparable VPN technologies.
• Capability in code-level debugging, including reading Go source code, understanding goroutines, locks, channels, pprof profiles, and network interface operations.
• Understanding of cloud infrastructure (IaaS), CI/CD processes, containerized applications, and Kubernetes troubleshooting.
• Strong systems administration skills and experience troubleshooting across Linux, macOS, and Windows.
• Demonstrated success in creating reproducible test cases and detailed bug reports for engineering teams.
• Ability to articulate complex technical issues clearly to both technical and non-technical audiences.
• A curious and investigative approach to root cause analysis.
• Proficiency in programming or scripting languages such as Go, Python, and JSON.
• Experience with packet analysis tools.

Nice to have

• Experience with packet-level analysis tools.

Skills & tools

• Go
• Python
• JSON
• Linux
• macOS
• Windows
• TCP/IP
• Routing
• DNS
• Firewalls
• NAT
• VPNs
• Load Balancers
• WireGuard
• UDP Hole Punching
• STUN
• Kubernetes
• CI/CD
• Cloud IaaS
• pprof
• Docker

Practical notes

• Salary range: $115,000 - $144,000 USD.
• Benefits include health, vision, dental, retirement contributions, professional development budget ($1500 USD annually), and paid time off.
• Home office setup includes a company-provided laptop, monthly internet reimbursement, and a $500 USD stipend.
• Paid parental leave is available (20 weeks for birthing parents, 16 weeks for non-birthing parents).
• Tailscale is a remote-first company.
• Application deadline: Not specified.
• Visa sponsorship: Not specified.