Senior Level 2 Support Specialist — Remote

Happy Co.; Northern (KY); Hybrid; USD 60,000 - 90,000; Full time

Benefits offered by this job

Work from anywhere

Unlimited vacation time

Generous parental leave

Competitive pay

Monthly wellness/home office stipends

Job summary

HappyCo is seeking a Level 2 Support Representative in the United States (Pacific time). You will resolve escalated issues, partner with Product and Engineering, and help improve support processes and documentation.

This hands-on role requires strong technical troubleshooting across integrated SaaS platforms, excellent communication, and a customer-first mindset. Join a fast-growing PropTech-focused company that values growth, flexibility, and collaboration.

Qualifications

• 2–5+ years in a technical customer support or SaaS support operations role
• Demonstrated experience resolving complex, escalated support issues independently
• Strong technical troubleshooting skills across integrated SaaS platforms
• Proficiency with Zendesk or a similar ticketing platform; ability to configure views, macros, and triage workflows
• Experience interpreting customer-facing issues using logs, metrics dashboards, or internal tooling
• Excellent communication skills, with the ability to distill technical concepts into simple explanations
• Highly organized, with experience using G-Suite, Slack, and support documentation systems
• Comfortable operating in a fast-paced, collaborative environment

Responsibilities

• Act as a product and workflow expert for L1 agents and internal teams
• Host live troubleshooting and screen-share calls with customers to resolve complex issues faster
• Receive, investigate, and resolve escalated support tickets via Zendesk, phone, and email
• Troubleshoot complex platform issues involving integrations, data flow, permissions, and user access across multiple systems
• Use diagnostic tools to reproduce issues, document root causes, and inform cross-functional follow-up
• Collaborate with L3, Product, and Engineering during escalations with context and customer impact
• Partner with Support leadership to identify ticket trends and recommend improvements
• Own and maintain internal documentation, macros, and training content
• Contribute to support QA and calibration sessions for quality
• Track and analyze ticket trends and surface actionable insights
• Participate in retros, process feedback loops, and experiments to raise service level
• Deliver a customer experience reflecting HappyCo's values — clear, timely, helpful, thoughtful

Skills

Technical support

SaaS support

Zendesk

Troubleshooting

Communication

Documentation

Cross-functional collaboration

Tools

Zendesk Explore

Logging dashboards

Admin tools

Job description

HappyCo is seeking a Level 2 Support Representative in the United States (Pacific time). You will resolve escalated issues, partner with Product and Engineering, and help improve support processes and documentation.

This hands-on role requires strong technical troubleshooting across integrated SaaS platforms, excellent communication, and a customer-first mindset. Join a fast-growing PropTech-focused company that values growth, flexibility, and collaboration.