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Customer Support Engineer

2 days, 13 hours ago
United Kingdom
Full-time
Mid Level
Technical Support Engineer
Customer and Technical Support
DNS JIRA Kubectl Kubernetes Linux macOS TCP/IP
Apply Now
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
View All Jobs 23

Description

  • Serve as the primary escalation point for technically complex tickets from paying customers and own them through resolution.
  • Diagnose and troubleshoot advanced Tailscale issues, including ACL misconfigurations, subnet routing, exit nodes, and identity provider integrations.
  • Manage a ticket queue while meeting SLA targets for first response and resolution times.
  • Provide clear, accurate technical guidance that drives positive user outcomes and strong CSAT scores.
  • Balance a high daily ticket volume while maintaining depth in complex networking troubleshooting.
  • Partner with CX, Product, and Engineering to identify recurring friction points and advocate for user experience improvements.
  • Own escalations from Tier 1, including issues from free-tier users that are beyond Tier 1 scope.
  • Mentor Tier 1 teammates through ticket reviews, escalation guidance, and documentation contributions.

Requirements

  • 4+ years of experience in a technical support role at a SaaS company, with experience handling escalated or enterprise accounts.
  • Hands-on familiarity with Tailscale or comparable networking/VPN products such as WireGuard or traditional VPNs is strongly preferred.
  • Strong networking fundamentals, including TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing.
  • Ability to troubleshoot across macOS, Windows, Linux, and mobile platforms.
  • Experience with identity providers and SSO integrations such as Okta, Google Workspace, or Azure AD.
  • Basic experience troubleshooting Kubernetes environments, including pod networking, namespaces, and kubectl.
  • Familiarity with log analysis and CLI-based diagnostic tools to investigate issues independently before escalating.
  • Excellent written communication skills with the ability to explain complex technical concepts clearly and empathetically.
  • Familiarity with Jira and Slack for workflow management and cross-team collaboration.
  • A proactive approach to learning new technologies and staying current with evolving infrastructure tools.
  • A natural tinkerer’s mindset and curiosity, often demonstrated through personal projects, homelabs, or open-source contributions.

Benefits

  • Competitive total compensation package including base salary and equity.
  • UK base salary range of £76,630 to £95,590 GBP.
  • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage.
  • Remote-first work environment with flexibility in how and when you work.
  • Annual $1,500 USD professional development budget, plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off program.
  • Home office support including a company-owned Mac or PC, monthly home internet reimbursement, and $1,000 USD to customize your workstation.
  • Generous parental leave with top-ups for up to 26 weeks, available from day one.

Interested in this position?

Apply directly on the company website

Apply Now

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