Controller

About the role

About Us Clever Benefits is a growing healthcare technology company on a mission to simplify how healthcare and employee benefits are managed. Through a combination of technology, AI, and deep industry expertise, we build solutions that make benefits more accessible, transparent, and effective for employers and their employees. As part of a broader portfolio of operating companies, our finance team supports multiple businesses at various stages of growth-from established operating companies to newly launched ventures. This creates a unique opportunity to work across a diverse set of businesses while helping build scalable financial infrastructure that supports long-term growth. We're a collaborative, entrepreneurial team that values ownership, continuous improvement, and practical problem solving. About the Role We are seeking a hands-on Controller to lead accounting operations, financial reporting, internal controls, and accounting compliance across our portfolio of companies. This role combines strategic controllership responsibilities with direct accounting ownership. The Controller will personally own the accounting function for Clever Benefits, including day-to-day accounting operations, month-end close, financial reporting, and cash management, while also serving as the overall owner of accounting operations, accounting policy, financial reporting, and accounting controls across the broader portfolio. This role is ideal for an experienced accounting leader who enjoys rolling up their sleeves, thrives in a multi-entity environment, and takes pride in producing accurate, reliable financial information. The Controller will report directly to the Chief Financial Officer (CFO), manage a small accounting team, and work closely with company leadership, external accountants, legal counsel, banks, and operating teams across the portfolio. This is a remote position. Candidates located near our offices in the Phoenix, Arizona or Charleston, South Carolina areas are welcome to work from those locations, but proximity to an office is not required. Accounting & Financial Reporting Own the monthly, quarterly, and annual close process across the portfolio Own reconciliations, intercompany accounting, allocations, and accounting review processes across the portfolio Personally own day-to-day accounting operations for Clever Benefits, including accounts payable, accounts receivable, reconciliations, journal entries, month-end close, and financial reporting Prepare and review financial statements and supporting schedules Ensure financial reporting is accurate, timely, and increasingly aligned with GAAP Review transaction coding, classifications, reconciliations, and journal entries Establish and maintain accounting policies, documentation standards, and review procedures Research and resolve accounting issues involving debt, equity, acquisitions, ownership transactions, stock-based compensation, and other non-routine activity Retain accountability for accounting accuracy and financial reporting regardless of delegated execution Multi-Entity Accounting Own intercompany accounting, allocations, shared services charges, and related-party transactions Maintain accounting consistency across multiple legal entities Oversee accounting treatment for loans, advances, promissory notes, convertible instruments, equity issuances, and stock option plans Own revenue recognition, deferred revenue accounting, commission liability accounting, and other complex accounting areas across the portfolio Support accounting setup and integration of newly formed entities and incubation initiatives Own the accounting structure, financial controls, and accounting processes for newly formed entities Ensure balance sheet integrity and proper reconciliation of all significant accounts Directly perform accounting activities for Clever Benefits while directing, reviewing, and overseeing accounting execution across other portfolio entities Controls, Risk Management & Compliance Strengthen internal controls, approval workflows, and financial governance processes Establish appropriate segregation of duties and accounting review procedures Improve cash disbursement controls, spend management controls, fraud prevention processes, and payment authorization standards Own payroll accounting review, payroll allocations, and payroll approval processes Serve as primary accounting liaison to external CPA firms and tax advisors Support annual tax filings, compliance projects, 409A valuations, R&D credit studies, and accounting-related diligence efforts Maintain documentation and records necessary to support investor, lender, and transaction diligence Ensure accounting practices can withstand the scrutiny of outside investors, lenders, and potential acquirers Leadership & Team Management Directly manage and develop the Accounting & Operations Manager Establish accountability, priorities, and operating rhythms for the accounting function Provide guidance on accountin

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