Level 2 Support Representative

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.

• →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

• 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

• 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

• 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

• 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