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Customer Reliability Engineer

Tailscale· Customer Support
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Remote$115k - $144kfull-timePosted 3mo ago

About the role

Remote role focused on owning and resolving high-severity customer escalations, collaborating with Customer Success, Support, and Product/Engineering to bridge customer-reported issues with engineering fixes.

Responsibilities

  • 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.

Qualifications

  • 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

Skills

Required:Post-sales technical escalation managementCustomer communication under pressureNetworking (TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers)Overlay networking concepts (WireGuard, UDP hole punching, STUN)Go, Python, JSON programming/scriptingGo source reading and debuggingPacket-level analysis

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package including base salary, equity incentive plan and variable commission (for quota-based roles).
  • Comprehensive group benefits with no waiting period (health, vision, dental, and more).
  • Remote first company with opportunities for in-person collaboration as needed; corporate co-working program available.
  • Employer-funded retirement contributions with 0.75% of eligible compensation matched.
  • Occasional in-person company events and ability to connect with teammates globally.
  • Professional development stipend of $1500 USD annually and mentorship opportunities.
  • Paid time off and flexible PTO program.
  • Build-your-own home office setup with laptop choice, internet reimbursement, and workstation stipend.
  • Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents).
Last updated Sep 17, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
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