Senior Customer Support Engineer (Tier 3), Customer Escalations

• Join Tailscale's Escalation Engineering team, taking ownership of the most complex, ambiguous customer escalations where the root cause is not always obvious. • Partner closely with Support and Product/Engineering to close the gap between "customer has described a problem" and "engineering has what it needs to fix it." • Work issues to resolution or create fully documented handoffs that engineering can act on without delay. • Report directly to the Customer Escalations Team Lead.

• 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. • Be a genuine problem-solver who gets energy from untangling hard, ambiguous technical issues. • Be comfortable owning a live, high-stakes customer call, staying calm, building trust, and communicating clearly under pressure. • Have hands-on networking experience in production or homelab environments including TCP/IP, routing, DNS, firewalls, NAT, VPNs, and load balancers. • Have deep familiarity with overlay networking concepts such as WireGuard, UDP hole punching, and STUN. • Have code-level debugging capability: able to read Go source, reason about goroutines, locks, and channels, read pprof CPU and heap profiles, and understand network interface semantics. • Be comfortable with infrastructure concepts including cloud IaaS, CI/CD pipelines, containerised applications, and Kubernetes debugging. • Have strong systems administration skills and troubleshooting across Linux, macOS, and Windows. • Have a track record of independently building reproducible test cases and clear, evidence-backed bug reports. • Have strong technical storytelling skills, able to distil highly technical issues into clear narratives for both engineers and non-technical stakeholders. • Have proficiency with programming and scripting in Go, Python, or JSON. • Have experience with packet-level analysis.

• Have experience with Tailscale or comparable overlay networking and VPN products in production environments. • Have experience building engineering handoff packages with reproducible cases, log evidence, and version matrices. • Have experience identifying systemic issues across escalation patterns and translating them into product improvements. • Have experience creating runbooks, tooling, or documentation that raises the technical bar for support organisations. • Have experience with pprof profiling and Go runtime debugging specifically.

• 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 communicate leading theories. • Build engineering handoff packages that require minimal follow-up: reproducible case, log evidence, version matrix, impact scope, what's been ruled out, and a proposed engineering team to own the fix. • File and track issues for confirmed bugs, keeping the ticket and issue link intact so engineering retains full customer context. • Monitor for patterns across escalations to catch recurring or systemic issues early. • Translate learnings into product improvements, tooling, and runbooks that raise the technical bar for the whole Support organisation. • Partner with Support, CSE, and Product/Engineering while staying within the team's scope.

• Receive a salary between £90,850 and £113,760 GBP plus equity incentive plan. • Get comprehensive group benefits with no waiting period, including health, vision, and dental coverage. • Receive employer-funded retirement contributions matching dollar-for-dollar up to 0.75% of eligible compensation. • Take 20 weeks paid parental leave for birthing parents or 16 weeks for non-birthing parents. • Get $1,500 USD annually for professional development. • Receive a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD for home office setup. • Attend an annual company retreat and team off-sites. • Access flexible paid time off.

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. Founded in 2019 and fully distributed, Tailscale is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks and share access to internal tools.