Support Engineer (Tier 1) at Tailscale in Remote

Summary: Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a motivated Support Engineer (Tier 1) to join their growing team, responsible for providing high-quality support to users and resolving technical issues across a range of networking challenges. Responsibilities: - Act as the primary technical resource for our free user community, resolving a wide range of configuration and networking challenges to keep them unblocked - Manage a high-velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution - 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 Required Qualifications: - 1–4+ years of experience in a technical support or customer-facing role, with a track record of solving technical problems - A natural tinkerer's mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions - A foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing - Proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS's - Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers - Excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity - A proactive approach to learning new technologies and staying current with evolving infra tools Required Skills: Networking fundamentals, Troubleshooting skills Important Skills: Technical support experience, Operating systems proficiency Nice-to-Have Skills: Curiosity, tinkering, Jira, Slack 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.