Customer Service Specialist

InsurePay is a SaaS billing and payments platform looking for motivated individuals to join their Customer Support team. The role involves providing customer support for InsurePay's Pay-As-You-Go ecosystem, resolving payroll-related issues, and collaborating with internal teams to enhance the customer experience.

Responsibilities:

• Provide direct customer support for the unified InsurePay Pay-As-You-Go ecosystem (InsurePay, 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 InsurePay’s Pay-As-You-Go ecosystem
• 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
• 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 / 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, 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 knowledge, and AI-assisted support best practices

Requirements:

• Bachelor's degree or equivalent practical experience
• 2–3 years of experience in customer support roles involving payroll systems, payroll data, or payroll-related SaaS platforms
• Demonstrated experience supporting business customers in payroll, financial technology, HR technology, or insurance platforms
• Demonstrated experience and comfort using technology tools and applications, including Microsoft Excel and the broader MS Office suite
• Collaboration tools such as Teams, 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 in environments where automation, knowledge bases, or AI-assisted support tools are used to improve support delivery
• Workers' compensation insurance or Pay-As-You-Go insurance billing
• Integration between payroll providers and insurance platforms
• Experience contributing to AI-powered customer support tools, chatbots, or automation initiatives
• Experience working with API integrations or payroll partner ecosystems