Senior Customer Support Engineer (Tier 3), Customer Escalations

Tailscale is hiring a full-time Senior Customer Support Engineer (Tier 3), Customer Escalations for a remote role based in the United Kingdom. This opportunity suits technical specialists who excel at resolving the most complex customer challenges while creating clear pathways to engineering solutions.

The Opportunity

As fully remote Senior Customer Support Engineer (Tier 3), Customer Escalations at Tailscale you will take ownership of highly complex and unclear escalations arising after sale. Work each case through to completion or prepare a fully actionable open package so engineering can begin immediately. The role reports to the Customer Escalations Team Lead and requires close daily partnership with Support as well as Product and Engineering colleagues across the United Kingdom remote setting.

Responsibilities

• Own high-severity post-sales technical escalations from intake until resolution or complete engineering hand-off, conducting in-depth investigations and reproducing hard-to-isolate defects.
• Hold customer calls, extract logs and discuss evolving diagnostic theories openly.
• Build engineering hand-off packages requiring minimal further questions: reproducible case, log evidence with timestamps and node IDs, version matrix, impact scope, items already eliminated and proposed ownership team.
• Create and track confirmed bug records while preserving continuous ticket links that keep full customer context visible to engineering.
• Spot patterns across escalations to detect recurring or systemic issues early and convert insights into product refinements, tooling and runbooks that raise technical capability for the whole Support group.
• Partner with Support, customer success engineers and Product/Engineering while remaining strictly inside team boundaries.

Skills & Qualifications

• Four or more years in technical support or escalations at a SaaS or infrastructure company with proven ownership of enterprise-level escalated accounts.
• Genuine problem-solver who gains energy from untangling hard ambiguous technical issues.
• Confidence managing live high-stakes customer calls: remaining calm, building trust and communicating clearly with frustrated or highly technical clients under pressure.
• Hands-on networking experience in production or laboratory settings covering TCP/IP, routing, DNS, firewalls, NAT, VPNs and load balancers.
• Deep familiarity with overlay networking concepts including WireGuard, UDP hole punching, STUN and comparable VPN or networking products.
• Code-level debugging ability: reading Go source, reasoning about goroutines, locks and channels, interpreting pprof CPU and heap profiles and understanding network interface semantics.
• Comfort with infrastructure domains such as cloud IaaS, CI/CD pipelines, containerised applications and Kubernetes debugging.
• Strong systems administration skills and multi-platform troubleshooting across Linux, macOS and Windows.
• Proven track record of independently creating reproducible test cases plus clear evidence-based bug reports that engineering can act on directly.
• Strong technical storytelling that converts highly technical irregular issues into clear accounts suitable for engineers and non-technical stakeholders.
• Investigative mindset oriented toward root-cause analysis and evaluation of all pathways that deliver the best customer outcome.
• Proficiency programming or scripting in Go, Python and JSON together with packet-level analysis experience.

Working at Tailscale

Tailscale supplies software that makes secure interconnection of people and their devices straightforward no matter where they are located. People and teams of every size rely on it each day to protect networks and share access to internal tools. Founded in 2019 and fully distributed, the company is backed by Accel, CRV, Insight, Heavybit and Uncork Capital. Fair equitable compensation packages include base salary, equity and comprehensive benefits; the UK base salary range is £90,850–£113,760 GBP and individual offers vary with experience and skill set. The environment is inclusive and flexible, providing no-wait group cover for health, vision and dental, remote-first working with co-working options and social events, retirement matching up to 0.75 per cent, $1,500 USD yearly professional development funding, choice of company laptop plus monthly internet reimbursement and $500 USD workstation setup allowance, flexible paid time off and parental-leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents.

How to Apply

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