Customer Support Representative

About the job

Title: Customer Support Analyst (PayGo Support Team)

Reports to: Customer Support Leadership (Associate Director of Customer or Customer Support Manager)

Location: Remote (US) or Hybrid (Buffalo, NY)– in office T & TH

About the role:

InsurePay is looking for motivated, detail-oriented individuals who are passionate about customer support and excited to help deliver an industry-leading SaaS solution to the property and casualty market. You will be part of a geographically dispersed support team that serves customers across our unified Pay-As-You-Go ecosystem, including InsurePay, TRUPAY, and Payroll Connect products.

In this role, you will be a first point of contact for our customers—responding to inquiries, troubleshooting issues, and ensuring that each interaction reflects InsurePay’s commitment to accuracy, reliability, and superior client satisfaction in the Workers’ Compensation Pay-As-You-Go space.

You will build strong, direct client relationships and partner closely with internal teams to proactively resolve issues, refine processes, and continually improve the overall customer experience. You should enjoy working in a dynamic, fast-paced environment where each day is different and where your contributions directly shape how we scale and evolve as a company.

If you are ready to take on a new challenge and be truly part of building a company and a unified support organization, this is the role for you!

You’re excited about this opportunity because you will ....

Provide direct customer support for the unified InsurePay Pay-As-You-Go ecosystem (InsurePay, TRUPAY, and Payroll Connect) via phone, email, and chat, ensuring high-quality, timely responses to client needs.

Serve as a trusted partner to our customers by building strong, credible relationships grounded in rapid issue resolution, empathy, and a customer-first mindset, driving superior client satisfaction and retention.

Act as the “voice of the customer”, sharing feedback, trends, and insights with internal teams (e.g., Product, Engineering, Sales, Implementation, Marketing, Payroll Partner Coordination) to improve our products, processes, and overall customer experience.

Deepen your knowledge of InsurePay’s platform offerings, the property and casualty market, the needs of agencies, carriers, MGAs, payroll providers, and policyholders, and how our Pay-As-You-Go solutions fit into their business workflows.

Own customer inquiries end-to-end: log, triage, research, troubleshoot, and resolve issues; escalate when appropriate; and follow up to ensure a complete and satisfactory resolution for every case.

Collaborate cross-functionally with fellow support analysts and other departments to coordinate responses, resolve recurring issues, and contribute to a seamless and consistent customer experience across all Pay-As-You-Go products.

Identify and resolve complex issues by researching data, system behavior, and configurations; analyze information to determine the most effective and efficient solution; and clearly communicate findings and next steps to customers and internal stakeholders.

Support Payroll Connect / InsurePay Connect workflows, including manually retrieving and processing payroll data, monitoring registration and onboarding progress, and following up with partners and customers to ensure timely completion of required steps.

Work with structured data (e.g., XML, CSV, TXT files) and tools like Microsoft Excel to validate, interpret, and reconcile payroll and premium information where needed.

Document knowledge and processes by contributing to internal knowledge bases, playbooks, and best practices that help scale support across the unified team and improve the consistency of our responses.

Proactively identify patterns and recurring issues, recommend process or product improvements, and help drive initiatives that raise overall customer satisfaction and operational efficiency.

As you grow in the role, mentor peers and new hires, sharing product knowledge, best practices, and tips for handling complex customer scenarios across our various products.

We’re excited about you because you ….

Are at the beginning of your customer support career, with a strong desire to grow within a fast-paced SaaS and Insurtech environment.

Are proactive, positive, and a self-starter, and you thrive as a collaborative team player with a track record of driving improvements that enhance customer satisfaction and internal efficiency.

Have a genuine passion for customer experience, process excellence, and building the kind of support organization that customers and colleagues love to work with.

Communicate clearly and effectively—both cross-functionally (with Sales, Product, Marketing, Engineering, and other teams) and externally with customers—across multiple channels (email, phone, video, and written documentation).

Can digest complex or technical data and explain it in a way that is clear, concise, and accessible for different audiences, including non-technical users.

Bring strong organization, time management, and prioritization skills, with the ability to manage multiple cases and stakeholders in a dynamic environment.

Think strategically about how to improve processes and experiences while also being comfortable executing tactically and rolling up your sleeves to solve day-to-day problems.

Have a customer-first mindset, strong problem-solving abilities, and a calm, professional demeanor under pressure.

Experience

Bachelor’s degree or equivalent practical experience

2-3 years’ of experience providing direct customer support, preferably for enterprise-level SaaS platforms or other technology products serving business customers

Demonstrated experience and comfort using technology tools and applications, including:

Microsoft Excel and the broader MS Office suite

Collaboration tools such as Teams, Zoom, and similar platforms

Ticketing systems like Zendesk, workflow tools such as Salesforce, Jira, and comparable systems

Basic understanding of XML, CSV, and TXT file formats and comfort working with structured data files (especially in the context of payroll or financial data)

Experience working with payroll data, insurance billing, or Pay-As-You-Go workers’ compensation solutions is a strong plus.