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Customer Support Engineer

2 months ago
United States
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 20

Description

  • Serve as the primary escalation point for technically complex tickets from paying customers and Tier 1 support.
  • Diagnose and troubleshoot Tailscale-specific issues involving ACLs, 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.
  • Handle a high volume of daily ticket replies while maintaining depth in troubleshooting.
  • Partner with CX, Product, and Engineering to identify recurring friction points and improve the user experience.
  • Own escalations from Tier 1, including issues from free-tier users that require deeper investigation.
  • Mentor Tier 1 team members through ticket reviews, escalation guidance, and documentation contributions.

Requirements

  • 4+ years of experience in a technical support role at a SaaS company, including escalated or enterprise-tier accounts.
  • Hands-on familiarity with Tailscale or similar networking/VPN products such as WireGuard or traditional VPNs, preferred.
  • Strong working knowledge of networking fundamentals including TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing.
  • Ability to troubleshoot across macOS, Windows, Linux, and mobile platforms.
  • Experience working 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.
  • Excellent written communication skills with the ability to explain complex technical concepts clearly and empathetically.
  • Familiarity with Jira and Slack for internal workflow management and cross-team collaboration.
  • A proactive, curious mindset with an interest in learning new technologies and keeping current with evolving infrastructure tools.

Benefits

  • Competitive total compensation package with base salary, equity, and variable commission for quota-based roles.
  • US base salary range of $97,000 to $121,000.
  • Comprehensive health, vision, and dental benefits with no waiting period.
  • Remote-first work environment with flexibility to work from wherever you have wifi.
  • $1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off for life events, travel, and work-life integration.
  • Home office support including a company-owned laptop, monthly home internet reimbursement, and $1,000 USD for workstation setup.
  • Generous parental leave top-up for up to 26 weeks from day one.

Interested in this position?

Apply directly on the company website

Apply Now

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