
Senior Customer Support Engineer (Tier 3), Customer Escalations
Overview
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.
Job Description
If you're passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We're seeking a motivated Senior Customer Support Engineer (Tier 3), Customer Escalations to join our Escalation Engineering team.
Responsibilities
- - Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff.
- - Get on calls with customers, pull logs, and communicate with the customer about leading theories.
- - Build engineering handoff packages that require minimal follow-up questions.
- - File and track issues for confirmed bugs, keeping the ticket/issue link intact.
- - Monitor for patterns across escalations to catch recurring or systemic issues early.
Required Skills
- - 4+ years in a technical support or escalation role at a SaaS or infrastructure company.
- - A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues.
- - Comfortable owning a live, high-stakes customer call.
- - Hands-on networking experience in production or homelab environments.
- - Deep familiarity with overlay networking concepts.
- - Code-level debugging capability.
- - Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows.
- - Strong technical storytelling.
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.
- - Employer-funded retirement contributions.
- - 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.
About the company
Tailscale is a secure connectivity platform that enables teams to build private networks quickly and easily without the complexity of traditional VPNs. Built on the WireGuard protocol, Tailscale creates a peer-to-peer mesh network that securely connects devices, servers, and cloud resources with minimal configuration and low latency. The platform integrates with existing identity providers to enforce Zero Trust, identity-based access control, allowing organizations to securely access infrastructure, internal applications, and services across multi-cloud environments, Kubernetes clusters, CI/CD pipelines, and edge devices. With cross-platform support for systems including Linux, macOS, Windows, iOS, and Android, Tailscale helps developers, IT teams, and security professionals simplify network security while reducing operational overhead.
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