Senior Customer Support Engineer (Tier 3), Customer Escalations

Stack

Responsibilities

• ▹Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff, including deep-dive investigation and reproduction of hard-to-isolate bugs
• ▹Get on calls with customers, pull logs, and communicate about leading theories
• ▹Build engineering handoff packages requiring minimal follow-up: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what's been ruled out, and a proposed owning team
• ▹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 learnings into product improvements, tooling and runbooks
• ▹Partner with Support, CSE and Product/Engineering while staying within the team's scope

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 energized by untangling hard, ambiguous technical issues
• ▹Comfortable owning a live, high-stakes customer call: staying calm and building trust 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: reading Go source, reasoning about goroutines/locks/channels, reading pprof CPU/heap profiles, understanding network interface semantics
• ▹Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, Kubernetes debugging
• ▹Strong systems administration and troubleshooting skills across Linux, macOS and Windows
• ▹Track record of independently building reproducible test cases and clear, evidence-backed bug reports
• ▹Strong technical storytelling: distilling highly technical, ambiguous issues into clear narratives for engineers and non-technical stakeholders
• ▹Investigative mindset, curious to analyze root cause
• ▹Proficiency with programming/scripting in Go, Python, JSON
• ▹Experience with packet-level analysis

Soft skills

What we offer

• ▹US pay range: $115,000–$144,000/year
• ▹Inclusive, flexible environment
• ▹Competitive total compensation: base salary, equity incentive plan, and commission for quota-based roles
• ▹Comprehensive group benefits with no waiting period (health, vision, dental)
• ▹Remote-first company
• ▹Employer-funded retirement contributions, matched dollar-for-dollar up to 0.75%
• ▹Annual company retreat, team off-sites
• ▹$1,500/year for professional development
• ▹Flexible paid time off
• ▹Build-your-own home office: $500 one-time plus monthly internet reimbursement
• ▹Paid parental leave: 20 weeks for birthing parents, 16 weeks for non-birthing parents

About the company

Tailscale builds software that makes it easy to securely interconnect people and their devices wherever they are, via a WireGuard-based overlay network. Founded in 2019, fully distributed, backed by Accel, CRV, Insight, Heavybit and Uncork Capital.