Customer Support Engineer (Tier 2) Tailscale

HelpfulRemote; Northern (KY); Hybrid; USD 97,000 - 121,000; Full time

Benefits offered by this job

Equity

Benefits

Remote-first work

Job summary

HelpfulRemote is hiring for a remote-first role in the United States to support paying customers of a networking software company. You will diagnose issues from ACLs to identity providers, manage escalations, and uphold SLA/CSAT targets.

Requires 4+ years in technical SaaS support, strong networking knowledge, Kubernetes basics, and experience with Jira and Slack. Base salary ranges from $97,000 to $121,000 USD, with equity and benefits.

Qualifications

• 4+ years of technical support experience in a SaaS company.
• Strong networking fundamentals and multi-OS troubleshooting.
• Experience with SSO/identity providers and basic Kubernetes knowledge.
• Familiarity with Jira and Slack; excellent written communication.

Responsibilities

• Handle technically complex support tickets escalated from Tier 1.
• Diagnose issues including ACL misconfigurations, subnet routing, and identity provider integrations.
• Manage ticket queue with strong SLA and CSAT performance.

Skills

Networking fundamentals

TCP/IP

DNS

Subnetting

Firewalls

Multi-OS troubleshooting

SSO/Identity providers

Kubernetes basics

Jira

Slack

Written communication

Tools

Jira

Slack

Job description

This role supports paying customers of a networking software company by handling technically complex support tickets escalated from Tier 1. Work includes diagnosing issues like ACL misconfigurations, subnet routing, exit node setups, and identity provider integrations, while managing a ticket queue and maintaining strong SLA and CSAT performance.

The employer wants 4+ years of technical support experience in a SaaS company, ideally with escalated or enterprise accounts. Strong networking fundamentals (TCP/IP, DNS, subnetting, NAT, firewalls), multi‑OS troubleshooting, SSO/identity provider experience, basic Kubernetes knowledge, and familiarity with Jira and Slack are expected, along with excellent written communication.

The position is remote‑first and based in the United States, reporting to the Support Team Lead. Compensation includes a base salary in the $97,000–$121,000 USD range, plus equity and benefits.

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