Customer Support Engineer

Tailscale

Support Engineer handling complex support tickets for Tailscale customers in a remote first environment. Diagnosing advanced networking issues and mentoring junior team members.

Posted 7/17/2026full-timeRemote • 🇬🇧 United KingdomMid-LevelSenior💰 £76,630 - £95,590 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in troubleshooting complex networking issues, particularly with Tailscale and related technologies, while maintaining high customer satisfaction through effective communication and problem resolution. Proficient in managing technical escalations and mentoring junior team members to enhance overall support capabilities.

Highest-signal resume keywords

Technical Support ExperienceNetworking FundamentalsTailscale or Comparable VPN ProductsIdentity Provider and SSO IntegrationTroubleshooting Across Multiple Operating Systems

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

TCP/IPDNSSubnettingFirewallsNAT TraversalRoutingKubernetesLog AnalysisCLI Diagnostic ToolsTroubleshooting

Soft Skills

Excellent Written CommunicationEmpathyCuriosityMentoring

Tools & Technologies

JiraSlackOktaAzure ADGoogle Workspace

Industry Keywords

SaaSTechnical EscalationCustomer SatisfactionTicket ManagementUser Experience

Tech Stack

Tools & technologies

AzureDNSFirewallsKubernetesLinuxMacOSNode.jsTCP/IP

About the role

Key responsibilities & impact

Serve as the primary escalation point for technically complex tickets raised by paying customers, taking full ownership through to resolution.
Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing/exit node configurations, and integration with identity providers (e.g. Okta, Azure AD).
Manage a ticket queue with a consistent focus on SLA adherence, ensuring timely first responses and resolutions.
Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.
Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.
Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.
Own escalations of technically complex tickets from Tier 1, including those originating from free-tier users, ensuring issues beyond Tier 1's scope are resolved efficiently and thoroughly.
Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.

Requirements

What you’ll need

4+ years of experience in a technical support role within a SaaS company, with demonstrated experience handling escalated or enterprise-tier accounts.
Hands-on familiarity with Tailscale or comparable networking/VPN products (i.e. WireGuard, traditional VPNs) strongly preferred.
Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.
Strong working knowledge of networking fundamentals - TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing - with the ability to apply this knowledge to real-world troubleshooting scenarios.
Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile platforms.
Experience working with identity providers and SSO integrations (e.g. Okta, Google Workspace, Azure AD) as they relate to device or user authentication.
Basic experience troubleshooting Kubernetes environments, including familiarity with pod networking, namespaces, and common CLI tools such as kubectl.
Familiarity with log analysis and CLI-based diagnostic tools to independently investigate issues before escalating.
Excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.
Familiarity with Jira and Slack to manage internal workflows and collaborate effectively across distributed teams.
Maintain a proactive approach to learning new technologies and staying current with evolving infra tools.

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.