Level 2 Support Representative

HappyCo; United States Virgin Islands; On-site; USD 65,000 - 90,000; Full time

Benefits offered by this job

Work from anywhere

Unlimited vacation

Parental leave

Wellness stipend

Home office stipend

Job summary

HappyCo is looking for a Level 2 Support Representative to resolve escalated issues and deliver outstanding customer experiences across our SaaS platform. This is a hands-on, technically involved role that thrives on solving challenging system‑level problems.

You’ll collaborate with L1, Product, and Engineering to troubleshoot complex data flows, permissions, and integrations, and contribute to internal knowledge bases to raise service quality.

Qualifications

• 2–5+ years in a technical customer support or SaaS support role.
• Proven ability to resolve escalated issues independently.
• Strong troubleshooting across integrated SaaS platforms, including data flow and permissions.
• Experience with Zendesk and configuring views, macros, and triage workflows.
• Ability to read logs and dashboards to identify root causes.
• Excellent communication and ability to explain complex concepts simply.
• Highly organized with experience using G‑Suite and Slack.
• Comfortable in a fast-paced, collaborative environment.

Responsibilities

• Act as product and workflow expert for L1 agents and internal teams.
• Host live troubleshooting and screen-ups on calls with customers to resolve complex issues faster.
• Receive, investigate, and resolve escalated tickets via Zendesk, phone, and email.
• Troubleshoot platform issues involving integrations, data flow, permissions across systems.
• Use diagnostic tools to reproduce issues, document root causes, and inform follow‑ups.
• Collaborate with L3, Product, and Engineering during escalations, contributing context and impact.
• Partner with Support leadership to identify ticket trends and improve workflows.
• Own and maintain internal documentation, macros, and training content.
• Track ticket trends and surface actionable insights for improvements.
• Participate in retros, process feedback loops, and support experiments.

Skills

Technical customer support

Escalated issue resolution

Cross-functional collaboration

Strong communication

Tools

Zendesk

Zendesk Explore

G‑Suite

Slack

Job description

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

About HappyCo

Founded in 2011, HappyCo (happy.co) builds mobile and cloud solutions to enable real‑time property data. Our flagship product suite 'Happy Property’ has more than 5 million units on its platform.

We’re everyday people with a shared purpose — improving the lives of others. Our team is made up of thinkers, talkers, planners, makers, builders, and everything in between. Together, we’re turning our passions into happier communities!

When customers use our software, their communities get stronger. Our tools empower everyone in multifamily property management to improve their operations and maximize returns, which means they’re building better experiences for their residents. Learn more about our Product Vision here!

Our HappyCo Culture

HappyCo strives to build better communities. So naturally, we are dedicated to making our own community an enjoyable place that allows us to do our best work. We’re devoted to building an inclusive, supportive culture that empowers each HappyCo’er to succeed and grow. To learn more about our culture, check out our careers page!

We Offer:

• Work from anywhere supported by a flexible company culture
• Opportunity to work for one of the fastest‑growing technology companies in the PropTech industry
• Unlimited vacation time
• Generous paid parental leave
• Competitive and equitable pay
• Monthly stipends to support Wellness and Home Office expenses

Find out more about our US Employee Benefits here!

We believe in supporting people to do their best work and thrive, and building a diverse, equitable, and inclusive company is core to our mission. Our goal is to ensure that HappyCo upholds an inclusive environment where all people feel that they are equally respected and valued, whether they are applying for an open position or working at the company. We welcome applicants of any educational background, gender identity and expression, sexual orientation, religion, ethnicity, age, citizenship, socioeconomic status, disability, and veteran status. HappyCo is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures.

We may use artificial intelligence (AI) tools to support parts of the hiring process, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.