Simple, secure networks for teams of any scale. Built on WireGuard.
Senior Customer Support Engineer, Customer Escalations
Location
Canada
Posted
6 days ago
Salary
$154.1K - $193.0K / year
Seniority
Senior
Job Description
Senior Customer Support Engineer, Customer Escalations
Tailscale
• 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.
Job 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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Senior Customer Support Engineer, Customer Escalations
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• 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
Senior Customer Support Engineer – Customer Escalations
TailscaleSimple, secure networks for teams of any scale. Built on WireGuard.
• 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
• Provide exceptional support to customers via phone, chat, email, and customer portal. • Diagnose, troubleshoot, and resolve application, workflow, and configuration issues. • Serve as a trusted advisor by helping customers maximize the functionality of our solutions. • Escalate complex issues to the appropriate internal teams while providing complete documentation. • Collaborate cross-functionally with Product, Engineering, Billing, and other internal departments to resolve customer issues. • Document all customer interactions and troubleshooting steps accurately and thoroughly. • Represent the voice of the customer by providing feedback that helps improve our products and services. • Identify opportunities to improve support processes and customer experience. • Utilize internal knowledge bases and support tools to research and resolve issues. • Demonstrate empathy, professionalism, and strong communication during every customer interaction. • Contribute to the development and maintenance of internal knowledge base articles. • Meet or exceed departmental performance metrics, including customer satisfaction, quality, productivity, and SLA goals. • Continuously expand product knowledge and stay current on new features and enhancements.
• Atuar no suporte técnico para clientes utilizando a plataforma de folha de pagamento digital • Identificar e solucionar problemas técnicos relacionados à folha de pagamento digital • Interagir com os clientes para entender suas necessidades e oferecer suporte personalizado • Documentar e reportar incidentes técnicos para a equipe de desenvolvimento


