Customer Support Engineer (Tier 2)

Tailscale is a fully distributed company building software to make secure networking effortless. We are seeking a Customer Support Engineer (Tier 2) to join our support team, serving as the primary escalation point for technically complex tickets from paying customers.

• Own and resolve escalated technical issues, including ACL misconfigurations, subnet routing/exit node configurations, and identity provider integrations (Okta, Azure AD).
• Manage ticket queue with SLA adherence and maintain high CSAT scores.
• Mentor Tier 1 colleagues and contribute to documentation.

• 4+ years of technical support experience in a SaaS company, including handling escalated accounts.
• Strong networking fundamentals: TCP/IP, DNS, subnetting, firewalls, NAT traversal, routing.
• Proficiency across macOS, Windows, Linux, and mobile platforms.
• Experience with identity providers and SSO integrations.
• Basic Kubernetes troubleshooting experience (pod networking, namespaces, kubectl).
• Familiarity with log analysis and CLI diagnostic tools.
• Excellent written communication.

US Pay Range: $97,000—$121,000 USD, plus equity and comprehensive benefits.

• Equity incentive plan
• Health, vision, and dental insurance
• Employer-funded retirement contributions with dollar-for-dollar match up to 0.75% of eligible compensation
• Flexible paid time off
• Paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing parents)
• $1,500 USD annual professional development budget
• Home internet reimbursement and $500 workstation customization stipend
• Annual company retreat and team offsites

Apply via the Greenhouse link.