Senior Finance Operations Analyst

About the position We're seeking a detail-oriented Senior Finance Operations Analyst to serve as the operational backbone of our finance team. This role reports directly to the Controller and will collaborate closely with the CFO, external auditors, tax advisors, PE investors and cross-functional business partners. This sits at the intersection of accounting, operations, and strategic support—requiring someone who can manage the daily financial workflow while thinking critically about process improvement and controls. You'll be the go-to person keeping our financial operations running smoothly during an exciting growth phase that includes a recent acquisition, our first audit and evolving investor reporting requirements. This isn't a traditional bookkeeping role. We need someone who can see both the trees and the forest—executing daily tasks with precision while identifying issues before they become problems and proposing solutions proactively. If you have (or are pursuing) your CPA and thrive in environments where you can build processes from the ground up, this role offers significant growth potential. Must be local to Chicago and be available to come into the River North office, as needed.

Responsibilities

• Accounts Receivable: Generate customer invoices, monitor outstanding AR aging, proactively follow up on collections, and manage the cash application process
• Accounts Payable: Review and process weekly AP runs, manage vendor relationships and inquiries, ensure timely and accurate payment processing
• Cash Management: Perform daily bank reconciliations, process ad hoc payments and customer refunds, maintain cash position visibility
• Specialized Payments: Prepare and process weekly physician payment schedules, manage affiliate and commission payments, oversee expense reimbursements
• Month-End Close: Own the month-end close process and tasks, ensure accurate and timely financial record-keeping
• Prepare monthly financial operations summaries and variance analysis
• Develop and maintain weekly liquidity and cash flow reporting for covenant compliance monitoring
• Create ad hoc financial reports for leadership and stakeholders
• Support the preparation of materials for PE investors, lenders, and auditors
• Identify inefficiencies in current processes and recommend solutions
• Develop and document standard operating procedures for financial workflows
• Implement controls and segregation of duties frameworks
• Support finance team integration efforts related to acquisitions
• Serve as the first point of contact for finance-related operational questions from across the business

Requirements

• Education: Bachelor's degree in Accounting, Finance, or related field
• Experience: 2-4 years in accounting or finance operations roles; experience with month-end close processes
• Technical Skills:
• Advanced Excel proficiency (pivot tables, VLOOKUPs, complex formulas)
• Experience with cloud-based accounting systems (Xero, QuickBooks Online, NetSuite, or similar)
• Understanding of GAAP accounting principles
• Mindset:
• Exceptional attention to detail with a "trust but verify" approach
• Strong analytical and problem-solving abilities
• Ability to manage competing priorities and meet deadlines in a fast-paced environment
• Self-starter who takes initiative without needing constant direction
• Proactive communicator who surfaces issues/ risks early and proposes solutions

Nice-to-haves

• CPA: Active CPA license or currently pursuing CPA certification
• Audit Background: Big 4, national, or regional public accounting firm experience (the ability to think like an auditor—questioning, documenting, and validating—is highly valued)
• Startup/High-Growth Experience: Comfort with ambiguity, changing priorities, and building processes in a dynamic environment
• Experience supporting financial audits or preparing audit workpapers
• Familiarity cash flow forecasting
• Experience in healthcare, SaaS, or multi-entity environments

Benefits

• Competitive salary of $80,000 to $100,000 annually
• Comprehensive Benefits Program: Medical, Dental, Vision, 401k, Tax Exempt Student Loan Repayment, and Commuter Benefits
• A mission-driven work environment committed to a spirit of support, growth, and achievement
• Performance-based career growth opportunities
• A front-row seat for the exponential growth of a booming education tech company
• Work/life balance

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