Senior Customer Support Engineer (Tier 3), Customer Escalations

3 days, 15 hours ago
Full-time
Senior
DevOps and Infrastructure
Tailscale

Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services
51-250
Founded 2019
$115M raised

Description

  • Own high-severity customer escalations from intake through resolution or engineering handoff.
  • Investigate complex, ambiguous technical issues, including reproducing hard-to-isolate bugs.
  • Join customer calls, gather logs, and communicate leading theories clearly under pressure.
  • Build detailed engineering handoff packages with reproducible cases, evidence, impact scope, and ownership recommendations.
  • File and track confirmed bug issues while preserving full customer context.
  • Monitor escalation patterns to identify systemic issues and inform product, tooling, and runbook improvements.
  • Partner with Support, Customer Support Engineering, and Product/Engineering within the team’s scope.

Requirements

  • 4+ years in a technical support or escalation role at a SaaS or infrastructure company.
  • Experience owning escalated or enterprise-tier customer accounts.
  • Hands-on networking experience with TCP/IP, routing, DNS, firewalls, NAT, VPNs, and load balancers.
  • Deep familiarity with overlay networking concepts such as WireGuard, UDP hole punching, and STUN.
  • Ability to read Go source code, reason about goroutines/locks/channels, and interpret pprof CPU/heap profiles.
  • Comfort with cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging.
  • Strong systems administration and troubleshooting skills across Linux, macOS, and Windows.
  • Proficiency with Go, Python, and JSON for programming or scripting.
  • Experience with packet-level analysis.
  • Preferred: experience with comparable VPN/networking products.

Benefits

  • Competitive total compensation package with base salary and equity incentive plan.
  • UK base salary range of £90,850 to £113,760 GBP.
  • Comprehensive health, vision, and dental benefits with no waiting period.
  • Remote-first work environment with flexible work arrangements.
  • Employer-funded retirement contributions with company match.
  • $1,500 USD annually for professional development, plus mentorship and coaching.
  • Flexible paid time off.
  • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.
  • Home office support, including a company laptop, monthly internet reimbursement, and $500 USD for workstation setup.

Interested in this position?

Apply directly on the company website

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