[Hiring] Senior Customer Support Engineer (Tier 3), Customer Escalations @Tailscale

Role Description

If you're passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We're seeking a motivated Senior Customer Support Engineer (Tier 3), Customer Escalations to join our Escalation Engineering 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 alternatively a fully-documented handoff that engineering can act on without delay.

As a Senior Customer Support Engineer (Tier 3), Customer Escalations, you'll partner closely with Support and Product/Engineering to close the gap between "customer has described a problem" and "engineering has what it needs to fix it." This role reports directly to the Customer Escalations Team Lead.

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.
• 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
• A proposed engineering team to own the fix
• File and track issues for confirmed bugs, keeping the ticket/issue link intact.
• Monitor for patterns across escalations to catch recurring or systemic issues early.
• Translate what you learn into product improvements, tooling, and runbooks.
• Partner with Support, CSE, and Product/Eng, while staying within this team's scope.

Qualifications

• 4+ years in a technical support or escalation role at a SaaS or infrastructure company.
• A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues.
• Comfortable owning a live, high-stakes customer call.
• 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.
• Code-level debugging capability: can read Go source, reason about goroutines/locks/channels.
• Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging.
• Strong systems administration skills across Linux, macOS, and Windows.
• Track record of independently building reproducible test cases and clear, evidence-backed bug reports.
• Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives.
• Investigative mindset; curious to analyze root cause and evaluate all options.
• Proficiency with programming/scripting in Go, Python, JSON.
• Experience with packet-level analysis.

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package including base salary, equity, and variable commission.
• Comprehensive group benefits with no waiting period for health, vision, dental, and more.
• Remote first company with opportunities for virtual and in-person social events.
• Employer-funded retirement contributions with a match up to 0.75% of eligible compensation.
• Support for personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program for any situation life throws your way.
• Build-your-own home office setup with a company-owned laptop and customization budget.
• Paid parental leave program with top-ups for birthing and non-birthing parents.