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.
About the role
- Senior Customer Support Engineer addressing high-severity technical escalations at Tailscale. Collaborating with engineering teams to resolve complex customer issues.
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: 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.
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