Senior Customer Support Engineer, Customer Escalations

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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

• Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs. • 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: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what's already been ruled out, and a proposed engineering team to own the fix. • File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context. • Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org. • Partner with Support, CSE, and Product/Eng, while staying within this team's scope

🎯 Requirements

• 4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts. • A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues • Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure. • Hands-on networking experience in production or homelab environments: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers. • Deep familiarity with overlay networking concepts — WireGuard, UDP hole punching, STUN — and comparable VPN/networking products. • Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics. • Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging. • Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows. • Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly. • Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders. • Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution • Proficiency with programming/scripting in Go, Python, JSON • Experience with packet-level analysis

🏖️ 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