Technical Support Specialist providing hands - on telecom support and client issue resolution at Pathway Communications in a hybrid setting.
About the role
- Support Engineer solving complex technical issues for Tailscale customers in a remote capacity. Part of a distributed team focused on delivering excellent customer support.
Responsibilities
- Serve as the primary escalation point for technically complex tickets raised by paying customers.
- Diagnose and troubleshoot advanced Tailscale-specific issues.
- Manage a ticket queue with a consistent focus on SLA adherence.
- Drive positive user outcomes and maintain high CSAT scores.
- Balance a high volume of daily ticket replies while maintaining the technical depth.
- Partner cross-functionally to identify recurring friction points.
- Own escalations of technically complex tickets from Tier 1.
- Mentor and support Tier 1 colleagues through ticket reviews.
Requirements
- 4+ years of experience in a technical support role within a SaaS company.
- Hands-on familiarity with Tailscale or comparable networking/VPN products strongly preferred.
- Display a natural tinkerer’s mindset and a deep curiosity for how things work.
- Strong working knowledge of networking fundamentals - TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing.
- Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile platforms.
- Experience working with identity providers and SSO integrations.
- Basic experience troubleshooting Kubernetes environments.
- Familiarity with log analysis and CLI-based diagnostic tools.
Benefits
- An inclusive, flexible environment where you can be your authentic self.
- A competitive total compensation package.
- Comprehensive group benefits with no waiting period.
- Remote first company—most of our teams work fully remotely.
- Connect with other Tailscalars IRL.
- Support for your personal and professional development.
- Paid time off and a healthy work-life integration.
- A build-your-own home office setup.
- Generous parental leave program from your first day.
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