Customer Support Engineer

Overview

Job Description

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.

Required Skills

• - 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.

Benefits

• - An inclusive, flexible environment where you can be your authentic self.
• - A competitive total compensation package including base salary, an equity incentive plan and variable commission (for quota-based roles).
• - Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family.
• - Remote first company with flexibility in how and when you work.
• - Support for your personal and professional development with $1500 USD annually for professional development.
• - Paid time off and a flexible program to support any situation life throws your way.
• - A build-your-own home office setup with a company-owned laptop and $1000 USD to customize your workstation.
• - Generous parental leave program from your first day.