Customer Support Engineer

Key Responsibilities

• Serve as the primary escalation point for technically complex tickets raised by paying customers, taking full ownership through to resolution.
• Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing/exit node configurations, and integration with identity providers (e.g. Okta, Azure AD).
• Manage a ticket queue with a consistent focus on SLA adherence, ensuring timely first responses and resolutions.
• Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.
• Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.
• Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.
• Own escalations of technically complex tickets from Tier 1, including those originating from free-tier users, ensuring issues beyond Tier 1's scope are resolved efficiently and thoroughly.
• Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.

What We Are Looking For

• 4+ years of experience in a technical support role within a SaaS company, with demonstrated experience handling escalated or enterprise-tier accounts.
• Hands-on familiarity with Tailscale or comparable networking/VPN products (i.e. WireGuard, traditional VPNs) strongly preferred.
• Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.
• Strong working knowledge of networking fundamentals - TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing - with the ability to apply this knowledge to real-world troubleshooting scenarios.
• Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile platforms.
• Experience working with identity providers and SSO integrations (e.g. Okta, Google Workspace, Azure AD) as they relate to device or user authentication.
• Basic experience troubleshooting Kubernetes environments, including familiarity with pod networking, namespaces, and common CLI tools such as kubectl.
• Familiarity with log analysis and CLI-based diagnostic tools to independently investigate issues before escalating.
• Excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.
• Familiarity with Jira and Slack to manage internal workflows and collaborate effectively across distributed teams.
• Maintain a proactive approach to learning new technologies and staying current with evolving infra tools.