Senior Escalations Engineer – SaaS Networking & Support

Tailscale; United Kingdom; On-site; GBP 90,850 - 113,760; Full time

Benefits offered by this job

Inclusive environment

Competitive compensation

Benefits package

Remote-first culture

Retirement contributions

Team retreats and travel

Professional development stipend

Flexible PTO

Home office setup allowance

Parental leave

Job summary

Tailscale is hiring a Senior Customer Support Engineer (Tier 3) to own escalations and drive resolution for complex issues. You’ll work with Support and Engineering to turn customer-reported problems into actionable engineering handoffs.

In this remote-first role, you’ll lead investigations, gather logs, and build reproducible test cases. You’ll communicate clearly with customers and engineers while helping drive product improvements across teams.

Qualifications

• 4+ years in a technical support or escalation role at a SaaS or infrastructure company.
• Strong problem-solving, capable of untangling ambiguous issues.
• Experience leading live customer calls under pressure.
• Hands-on networking experience: TCP/IP, DNS, VPNs, NAT, firewalls.
• Familiar with overlay networking: WireGuard, UDP hole punching, STUN.
• Ability to read Go code and debug concurrent systems.
• Experience with cloud IaaS, CI/CD, containers, Kubernetes debugging.
• Proficient in Linux, macOS, Windows administration.
• Proven ability to write reproducible test cases and bug reports.
• Strong technical storytelling for engineers and stakeholders.
• Investigative mindset to find root causes.
• Proficiency with Go, Python, JSON.
• Experience with packet-level analysis.

Responsibilities

• Own high-severity escalations from intake to resolution or engineering handoff.
• Conduct deep-dive investigations and reproduce difficult-to-isolate bugs.
• Join calls with customers, pull logs, and discuss leading theories.
• Create engineering handoff packages with evidence, version matrices, and impact scope.
• Log and track confirmed bugs, maintaining full customer context for engineers.
• Monitor for patterns across escalations to trigger improvements.
• Collaborate with Support, CSE, and Product/Eng teams.

Skills

Escalation management

Customer communication

Problem solving

Live high-stakes calls

Networking basics

Technical storytelling

Investigative mindset

Education

Bachelor's degree in a relevant field

Tools

Go

Python

JSON

Kubernetes

Job description

Tailscale is hiring a Senior Customer Support Engineer (Tier 3) to own escalations and drive resolution for complex issues. You’ll work with Support and Engineering to turn customer-reported problems into actionable engineering handoffs.

In this remote-first role, you’ll lead investigations, gather logs, and build reproducible test cases. You’ll communicate clearly with customers and engineers while helping drive product improvements across teams.