Level 2 Support Representative

Support Full-Time 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 You'll Be Measured Resolution time, accuracy, and quality of escalated ticket handling Depth and clarity of root cause investigations and documentation Contribution to L1 enablement and knowledge documentation Internal QA scores and peer/stakeholder feedback Participation in process improvement and proactive support initiatives Keys to Optimum Happiness at HappyCo Thrives in ambiguity and proactively builds clarity Focuses on long-term impact over quick wins Enables others through systems, not mandates Leverages technology and AI to empower people and simplify complexity Embraces the challenges and rewards of growing in a scaleup environment