Senior Customer Support Engineer, Customer Escalations

Tailscale

Senior Customer Support Engineer handling complex customer escalations for Tailscale. Collaborating across teams to resolve ambiguous technical issues and improve product support.

Posted 7/17/2026full-timeRemote • 🇬🇧 United KingdomSenior💰 £90,850 - £113,760 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in technical support and escalation management, with a strong focus on problem-solving, customer communication, and technical storytelling. Proficient in networking concepts, code-level debugging, and systems administration across various platforms.

Highest-signal resume keywords

Technical Support ExperienceNetworking ConceptsCode-Level DebuggingSystems AdministrationTechnical Storytelling

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

TCP/IPRoutingDNSFirewallsNATVPNsGo ProgrammingPython ProgrammingPacket-Level AnalysisKubernetes Debugging

Soft Skills

Problem-SolvingCustomer CommunicationInvestigative MindsetCalm Under PressureBuilding Trust

Tools & Technologies

Cloud IaaSCI/CD PipelinesContainerized ApplicationsOverlay NetworkingLog Analysis Tools

Industry Keywords

SaaSInfrastructureTechnical EscalationEnterprise-Tier AccountsSupport Organization

Tech Stack

Tools & technologies

CloudDNSFirewallsGoKubernetesLinuxMacOSNode.jsPythonTCP/IP

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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

Comp & perks

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company—most of our teams work fully remotely.
Employer-funded retirement contributions.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Paid parental leave program.