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Tailscale Tier 2 Support Engineer

Tailscale

winnipeg, mb, Canada Full-time July 09, 2026

Found Description

Join Tailscale as a Tier 2 Support Engineer and provide expert technical assistance to a global user community. Your role will focus on resolving complex networking issues remotely.

This position calls for a support engineer experienced in SaaS environments with a strong grasp of networking fundamentals. You will handle technical escalations, troubleshoot advanced configurations, and mentor Tier 1 colleagues. Your proactive approach and curiosity for technology will greatly improve user experiences while driving high customer satisfaction scores.

Key Responsibilities: • Serve as primary escalation point for complex technical tickets • Diagnose advanced Tailscale-specific networking issues • Manage ticket queue meeting SLA requirements • Ensure positive user outcomes by providing accurate guidance • Mentor Tier 1 support staff through ticket reviews

Requirements: • Minimum 4 years in technical support, preferably SaaS • Hands-on experience with Tailscale or si...

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