Customer Support Engineer

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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.