Payroll Specialist

Customer Support Analyst (Pay Go Support Team)

Reports to:

Customer Support Leadership About the role

Insure Pay is looking for two 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 Insure Pay, TRUPAY, and Payroll Connect products.

Because our products sit at the intersection of insurance and payroll data, this role requires strong familiarity with payroll concepts, payroll files, and payroll workflows. You will work regularly with structured payroll data, investigate payroll reporting issues, and assist customers and partners in resolving payroll-related discrepancies.

As Insure Pay continues to evolve its AI-powered support strategy, you will also interact with AI-driven support tools, automation workflows, and knowledge systems that help scale customer support. This includes contributing to automation initiatives, improving knowledge base content, and collaborating on ways AI can improve resolution speed and accuracy.

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!

• Provide direct customer support for the unified Insure Pay Pay-As-You-Go ecosystem (Insure Pay, TRUPAY, and Payroll Connect) via phone, email, chat, and AI-assisted channels, ensuring high-quality, timely responses to client needs.
• Serve as a trusted partner to customers by building strong relationships grounded in rapid issue resolution, empathy, and a deep understanding of payroll-driven insurance billing workflows.
• 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.
• Develop deep knowledge of payroll processing, payroll file structures, payroll reporting cycles, and how payroll data drives premium calculations within Insure Pay’s Pay-As-You-Go ecosystem.
• Own customer inquiries end-to-end: log, triage, research, troubleshoot, and resolve issues; elevate 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.
• Investigate complex issues involving payroll data, payroll files, system configurations, and premium calculations, clearly communicating findings and solutions to customers and internal stakeholders.
• Support Payroll Connect / Insure Pay 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, TXT files) and tools like Microsoft Excel to validate, interpret, and reconcile payroll and premium information where needed.
• Contribute to AI-driven support initiatives, including improving chatbot responses, refining automation workflows, tagging tickets for AI training, and helping expand the support knowledge base.
• 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 while sharing expertise in payroll workflows, product…