Customer Support Engineer
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Job Description
Support Engineer handling complex support tickets for Tailscale customers in a remote first environment. Diagnosing advanced networking issues and mentoring junior team members.
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.
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.
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