Level 2 Support Representative

HappyCo is a company where people can grow their careers and work with like minded people, with no egos or politics. HappyCo is values driven and offers a flexible, supportive culture. Join HappyCo and Make Work Happy !

We're looking for a Level 2 Support Representative to join our team at HappyCo . This position must be located in the United States with the ability to work within the Pacific timezone.

The Position

As a Level 2 Support Representative at HappyCo , you will play a critical role in delivering exceptional customer experiences by resolving complex, escalated issues, partnering with cross-functional teams, and contributing to continuous support process improvements. You'll act as a subject matter expert on our platform, tools, and workflows — working closely with the L1 support team, Product, and Engineering to ensure fast, consistent, and high-quality outcomes for our customers. This is a hands-on, technically involved role for someone who thrives on solving challenging system-level problems, enabling teammates, and improving support infrastructure.

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, reduce back-and-forth, and build trust through real-time connection

- Receive, investigate, and resolve escalated support tickets via Zendesk, phone, and email — bringing urgency, accuracy, and empathy to every interaction

- Troubleshoot complex platform issues involving integrations, data flow, permissions, and user access across multiple systems

- Use diagnostic tools (e.g. Zendesk Explore, logging dashboards, internal admin tools) to reproduce issues, document root causes, and inform cross-functional follow-up

- Collaborate with L3, Product, and Engineering teams during escalations, contributing investigation summaries, context, and customer impact assessments

- Partner with Support leadership to identify ticket trends and recommend workflow, documentation, or product improvements

- Own and maintain internal documentation, macros, and training content to support L1 enablement and onboarding

- Contribute to support QA efforts and participate in calibration sessions to ensure consistency and quality

- Track and analyze ticket trends (e.g. FCR, resolution time, escalation types), surfacing actionable insights

- Proactively participate in retros, process feedback loops, and support experiments that raise our service bar

- Deliver a customer experience that reflects HappyCo 's values — clear, timely, helpful, and thoughtful

What We Think You Need to be Successful

Required

- 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, including data flow, system permissions, and third-party integrations

- 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, customer-friendly explanations

- Highly organized, with experience using G-Suite, Slack, and support documentation systems

- Comfortable operating in a fast-paced, collaborative, and continuously evolving environment

Preferred

- Experience in property management or PropTech environments

- Familiarity with tools like Jira, Notion and Gainsight

- Experience contributing to internal knowledge bases, agent enablement, or support automation

- Experience working in or alongside BPO or distributed support teams

- Understanding of SLA-based triage workflows, ticket prioritization, and escalation handling

- Exposure to APIs, system logs, or backend-to-UI debugging concepts

How Y