Skip to content
TailscaleTailscaleUnited States

Senior Customer Support Engineer , Customer Escalations

Senior Customer Support Engineer owning complex post-sales technical escalations for Tailscale's VPN networking product. Requires 4+ years in technical support, deep networking and Go debugging expertise, and the ability to drive issues to resolution or high-quality engineering handoff.

115k – 144k
Remote4+ YOESupport Engineering

About the role

Key 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.

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 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.

Compensation

  • US Pay Range: $115,000—$144,000 USD (base salary target for new hires; individual offers may vary based on experience and skill set).
  • Total compensation package includes base salary, equity incentive plan, and comprehensive benefits (health, vision, dental, retirement contributions, professional development, home office setup, parental leave, and more).

Skills

GoPythonTCP/IPDNSVpnWireguardKubernetesLinuxmacOSWindowsNetworkingDebuggingPacket Analysis
Cloudflare

Senior Technical Account Manager

CloudflareAustin, TX +2

Own post-sales technical support and architectural governance for Cloudflare's largest Enterprise customers. Serve as primary technical contact, proactively identify risks using AI tools, conduct reviews, drive resolutions, and advocate for customer needs with 8+ years customer-facing technical experience.

114k – 158k
Hybrid8+ YOESupport Engineering
Shield AI

Senior Engineer, Software Integration - Fleet Support (R5079)

Shield AIDallas, TX

Serve as software SME for Fleet Support, triaging and root-causing issues across fielded aircraft, mission software, and ground control systems while bridging field issues to engineering teams. Requires 5+ years in robotics/autonomy, strong C++ and Python skills, and Linux/hardware debugging experience.

120k – 180k
On-site5+ YOESupport Engineering
Clear Street

Senior Associate - Active Trading Support

Clear StreetDel Mar, CA

Provides front-line support for retail active trading platform, handling inquiries on accounts, PDT, onboarding, and billing via phone and chat during market hours. Requires 4+ years fintech/brokerage support, Series 7/63 licenses, and trading knowledge.

110k – 130k
Hybrid4+ YOESupport Engineering
Clear Street

Senior Associate - Active Trading Support

Clear StreetNew York, NY

Provides front-line support for retail active trading platform, handling inquiries on accounts, PDT, onboarding, and billing via phone and chat during market hours. Requires 4+ years fintech/brokerage experience, Series 7/63 licenses, and trading knowledge.

110k – 130k
Hybrid4+ YOESupport Engineering
Hospitable

Customer Advocate Lead (North America - Remote)

HospitableUnited States

Leads US remote support team to deliver exceptional customer experience via queue management, technical troubleshooting, coaching, and hands-on support (30-40% time). Requires SaaS support leadership experience improving metrics like response times and CSAT.

107k – 133k
RemoteSupport Engineering