Customer Reliability Engineer

• Take ownership of Tailscale's most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious. • Work those issues through to resolution, or to a fully documented handoff that engineering can act on without delay. • Partner closely with the Customer Success Team, Support Team, and Product/Engineering to close the gap between "customer has described a problem" and "engineering has what it needs to fix it". • Report directly to the Customer Reliability Engineer Team Lead. • Work remotely from anywhere in the United Kingdom at a fully distributed company.

• Have 4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated or enterprise-tier accounts. • Solve problems genuinely, drawing energy from untangling hard, ambiguous technical issues. • Own a live, high-stakes customer call, staying calm and communicating clearly with a frustrated or technical customer under pressure. • Bring hands-on networking experience from production or homelab environments, covering TCP/IP, routing, DNS, firewalls, NAT, VPNs, and load balancers. • Know overlay networking concepts deeply, including WireGuard, UDP hole punching, STUN, and comparable VPN products. • Debug at code level: read Go source, reason about goroutines, locks, and channels, read pprof CPU and heap profiles, and understand network interface semantics. • Work comfortably with infrastructure concepts including cloud IaaS, CI/CD pipelines, containerised applications, and Kubernetes debugging. • Bring strong systems administration and troubleshooting skills across Linux, macOS, and Windows. • Show a track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly. • Tell technical stories well, distilling ambiguous issues into clear narratives for engineers and non-technical stakeholders alike. • Bring an investigative mindset, curious to find root cause and evaluate every option to get customers to the best solution. • Be proficient with Go, Python, and JSON. • Have experience with packet-level analysis.

• Have worked on a VPN, overlay network, or similar connectivity product. • Have written runbooks or tooling that raised the technical bar across a support organisation. • Have spotted systemic issues by analysing patterns across escalations. • Have contributed to open-source Go projects.

• Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff, including deep-dive investigations and reproduction of difficult-to-isolate bugs. • Get on calls with customers, pull logs, and talk them through leading theories. • Build engineering handoff packages that need minimal follow-up, covering a reproducible case, log evidence with timestamps and node IDs, version matrix, impact scope, what's already been ruled out, and a proposed owning team. • File and track issues for confirmed bugs, keeping the ticket 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/Engineering while staying within the team's scope.

• Receive a competitive total compensation package including base salary and an equity incentive plan. • Access comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family. • Work remote-first with support for virtual and in-person social events and a corporate co-working programme at WeWork or similar spaces. • Get employer-funded retirement contributions matched dollar-for-dollar, up to 0.75% of your eligible compensation annually. • Attend the annual company retreat and team off-sites, connecting with teammates across Canada, the US, the UK, and Singapore. • Spend $1,500 USD annually on professional development, alongside mentorship, coaching, and internal promotion opportunities. • Take flexible paid time off that supports whatever life throws your way. • Build your own home office with a company-owned laptop of your choice, monthly home internet reimbursement, and $500 USD to customise your workstation. • Take paid parental leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents.

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices wherever they are. Teams of every size, from hobbyists to multinational corporations, use Tailscale to protect their networks and share access to internal tools. The company was founded in 2019, is fully distributed, and is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.