Customer Support Engineer

🕒 July 17

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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.

🎯 Requirements

• 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. • Comprehensive group benefits with no waiting period. • Remote first company—most of our teams work fully remotely. • Employer-funded retirement contributions. • 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. • Paid parental leave program.