AR & Billing Specialist
About the role We are looking for a detail-oriented and proactive AR & Billing Specialist to own the end-to-end accounts receivable and billing cycle, including invoicing, cash application, collections, and reconciliations across multiple programs and carrier relationships. This role also supports revenue reconciliations, investigates billing-to-revenue discrepancies, and analyzes variances against forecasts and P&L trends. You will collaborate cross-functionally with Operations, Data Analytics, Customer Success, Sales, and Accounting. The ideal candidate thrives in a fast-paced startup environment, brings strong analytical instincts, and is comfortable navigating complexity. What you'll do We need you to do all the things typical to the role: Billing & Invoicing Generate and issue accurate customer invoices on a timely basis, ensuring alignment with contract terms, fee schedules, and service activity Own day-to-day billing operations across multiple programs and carrier relationships Investigate and resolve billing discrepancies, short payments, and unapplied cash Collections & Cash Application Monitor AR aging and proactively follow up on outstanding balances Apply incoming payments, and reconcile customer accounts Prepare AR aging reports and provide regular updates on collections status to leadership Revenue Support & Reconciliation Support revenue reconciliations by reviewing billing activity against expected revenue Help identify and investigate revenue variances compared to forecasts, prior periods, and P&L trends Assist with month-end close tasks related to AR, billing, and revenue accounts, including reconciliations and journal entry support Cross-Functional Collaboration & Process Improvement Partner with Operations, Data Analytics, Customer Success, Sales, and Accounting to resolve billing and account issues Support audit requests by providing AR, billing, and revenue-related schedules and documentation Help improve and streamline AR, billing, and revenue reporting processes and internal controls Maintain accurate records and supporting documentation in compliance with company policies Qualifications Required 3+ years of experience in accounts receivable, billing, revenue operations, or general accounting Strong understanding of AR processes, billing workflows, cash application, collections, and reconciliations Familiarity with revenue concepts and the ability to analyze revenue fluctuations, billing trends, and P&L variances Experience with ERP or accounting systems (e.g., NetSuite, QuickBooks, or similar) Experience reading and navigating online banking systems and payment portals Proficiency in Excel or Google Sheets Strong analytical mindset with high attention to detail and accuracy Excellent organizational and time management skills Strong written and verbal communication skills Ability to work independently and manage multiple priorities in a dynamic environment Preferred Experience in insurance, insurtech, or TPA environments Experience with NetSuite (we are actively migrating to NetSuite) Experience with AP/expense management platforms such as Ramp Familiarity with BI/reporting tools (e.g., Looker) Startup experience Curiosity and openness toward using AI tools Benefits Generous health-insurance package with nationwide coverage, vision, & dental 401(k) retirement plan with employer matching Competitive PTO policy – we want our employees fresh, healthy, happy, and energized! Generous family leave policy after 8 months of continuous work Work from anywhere to facilitate your work life balance Apple laptop, large second monitor, and other quality-of-life equipment you may want. Technology is something that should make your life easier, not harder! At Reserv, we value diversity in backgrounds, perspectives, and life experiences and believe that diversity in viewpoints and critical thinking drives innovation, first-principles thinking, and success. We welcome applicants from all backgrounds and encourage those from all walks of life to apply. If you believe you are a good fit for this role, we would love to hear from you!