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 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