Customer Reliability Engineer Tailscale

HelpfulRemote; Northern (KY); Hybrid; USD 115,000 - 144,000; Full time

Job summary

HelpfulRemote is seeking a technical escalation specialist to own high-severity issues after customers purchase. You will investigate complex bugs, join customer calls to collect logs, and craft detailed handoff packages for engineering.

The role requires 4+ years in technical support or escalation within SaaS or infrastructure, with strong networking and cloud skills. This is a remote-first, full-time position in the United States, reporting to the Customer Reliability Engineer Team Lead.

Qualifications

• 4+ years in technical support or escalation roles at SaaS or infrastructure companies.
• Experience owning enterprise-tier accounts is required.
• Strong networking knowledge including TCP/IP, DNS, VPNs, NAT, and load balancers.
• Familiarity with overlay networking concepts like WireGuard and STUN.

Responsibilities

• Own the most complex, high-severity technical escalations after purchase.
• Investigate hard-to-reproduce bugs and gather logs during customer calls.
• Build detailed handoff packages to enable rapid engineering action.
• Identify recurring issues and help improve tooling and runbooks across the support org.

Skills

Networking knowledge

Go debugging

Python/JSON scripting

Linux/macOS/Windows admin

Kubernetes & cloud infra

Tools

Go

Python

JSON

Kubernetes

Job description

This role focuses on owning the most complex, high-severity technical escalations that come in after a customer has purchased Tailscale’s networking software. You’ll investigate hard-to-reproduce bugs, join customer calls to gather logs and evidence, and build detailed handoff packages so engineering can act quickly. You’ll also spot recurring issues and help improve tooling and runbooks across the support organization.

Candidates need at least 4 years in technical support or escalation roles at a SaaS or infrastructure company, with experience owning enterprise-tier accounts. Strong networking knowledge (TCP/IP, DNS, VPNs, NAT, load balancers) is required, along with familiarity with overlay networking concepts like WireGuard and STUN. Code-level debugging in Go, scripting in Python/JSON, systems administration across Linux, macOS and Windows, and comfort with Kubernetes and cloud infrastructure are also expected.

This is a full-time, remote-first position open to candidates based in the United States, with a stated pay range of $115,000 to $144,000 USD. The role reports to the Customer Reliability Engineer Team Lead and works closely with Customer Success, Support, and Product/Engineering teams.