Customer Support Engineer (Tier 2)

Tailscale makes secure networking effortless, connecting people and devices anywhere. Fully distributed, backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

We're seeking a motivated Support Engineer (Tier 2) to join our growing support team. You'll serve as the face of the company, handling complex tickets, escalating from Tier 1, mentoring Tier 1 colleagues, and partnering with CX and Product/Eng. This role reports to the Support Team Lead.

• Serve as primary escalation point for technically complex tickets from paying customers.
• Diagnose and troubleshoot Tailscale-specific issues (ACL misconfigurations, subnet routing, exit nodes, identity provider integration).
• Manage ticket queue with SLA adherence.
• Drive positive user outcomes and maintain CSAT.
• Balance high volume of daily replies with technical depth.
• Partner cross-functionally to identify friction points.
• Own escalations from Tier 1, including free-tier users.
• Mentor Tier 1 colleagues.

• 4+ years technical support in SaaS, handling escalated/enterprise accounts.
• Hands-on familiarity with Tailscale or comparable networking/VPN products (WireGuard, traditional VPNs) preferred.
• Strong networking fundamentals: TCP/IP, DNS, subnetting, firewalls, NAT traversal, routing.
• Proficiency troubleshooting across macOS, Windows, Linux, mobile.
• Experience with identity providers and SSO (Okta, Google Workspace, Azure AD).
• Basic Kubernetes troubleshooting (pod networking, namespaces, kubectl).
• Familiarity with log analysis and CLI diagnostic tools.
• Excellent written communication.
• Familiarity with Jira and Slack.

CAN Pay Range $129,980—$162,140 CAD base salary, plus equity and benefits.

• Comprehensive group benefits (health, vision, dental)
• Employer-funded retirement contributions (match up to 0.75%)
• Flexible PTO
• Paid parental leave (20 weeks birthing, 16 weeks non-birthing)
• $1500 USD annual professional development
• Equipment stipend ($500 USD workstation customization) and monthly internet reimbursement
• Remote-first
• Annual company retreat, team offsites

Apply via the Greenhouse link.