Customer Support Engineer

About Tailscale Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. Job Description If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated Support Engineer (Tier 2) to join our growing team of support professionals. You will serve as the face of the company for teams and companies using Tailscale, handling a broad range of tickets that will help flex your technical muscles. As a Tier 2 engineer, you’ll be part of a distributed team focused on delivering excellent support to our customers and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Support Team Lead and will play a key role in our journey. 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. As a company, we strive to maintain fai