Support Engineer solving complex technical issues for Tailscale customers in a remote capacity. Part of a distributed team focused on delivering excellent customer support.
Responsibilities
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.
Senior Support Engineer troubleshooting AGFA healthcare IT solutions and cloud environments. Improving monitoring, preventing incidents, and supporting global customers through complex technical escalations.
Business Systems Technical Analyst supporting ERP, WMS, SQL, and integrations for a Canadian food company. Troubleshooting enterprise applications and delivering system improvements across operations.
Site Support Technician resolving hardware, software, and connectivity issues at Computershare, a global financial administration company. Supporting assets, workspaces, IT projects, and internal users.
Sr. Support Analyst providing first - level IT support and security triage for OPENLANE’s digital used - vehicle marketplace. Resolving employee hardware, software, access, and application issues.
Technical Support Engineer bridging Support and Engineering for Foundant’s nonprofit and philanthropic SaaS products. Investigating complex issues, managing escalations, and driving confirmed fixes.
Support Engineer resolving CRM, integration, and data issues for dealer management software. Supporting equipment dealerships through SQL diagnostics, APIs, monitoring, and AI - assisted workflows.
Support Analyst troubleshooting Cayenta’s utility enterprise software and CIS issues. Investigating applications, data, integrations, and SQL problems for North American customers.
Support Analyst resolving complex application, data, integration, and SQL issues for Cayenta’s utility and government software customers. Using AI - enabled tools, customer support expertise, and root - cause analysis.
Support Analyst troubleshooting Cayenta enterprise software, CIS, data, integrations, and SQL issues. Supporting utility and local - government customers through remote investigation and documentation.