Payroll Specialist

Customer Support Analyst (PayGo Support Team) Reports to: Customer Support Leadership About the role InsurePay 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 InsurePay, 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 InsurePay 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! 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, 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; 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 / 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. We’re excited about you because you ... Have a strong interest in building a career in SaaS customer support within the payroll and insurance technology space. Bring curiosity and enthusiasm for how AI, automation, and modern support tooling can improve customer experience and support operations. 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. Must Have Experience 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. Nice to Have Experience 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 Competitive compensation Generous vacation policy Full medical, dental, and vision packages 100% employer-paid Life and AD&D Insurance Optional LTD and STD coverage 100% employer-paid employee assistance program 401(k) with company match #J-18808-Ljbffr InsurePay