Controller

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 accounting treatment, close support activities, and process execution
• Review and oversee accounting work performed throughout the portfolio
• Delegate accounting projects and execution activities while maintaining ownership of accounting outcomes
• Help define appropriate ownership between bookkeeping, accounting operations, business operations, and controllership responsibilities
• Build a scalable accounting function capable of supporting continued growth across the portfolio

Equal Opportunity Employer

Clever Benefits is an equal opportunity employer committed to building an inclusive workplace where everyone can do their best work. We celebrate diversity and are committed to creating an environment where all employees feel respected, valued, and supported. We make employment decisions based on qualifications, merit, and business needs without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other protected characteristic under applicable law.

Work Authorization
This position is not eligible for employer-sponsored work authorization. Applicants must be legally authorized to work in the United States without requiring sponsorship now or in the future.

Requirements

Required

• Bachelor's degree in Accounting or Finance
• 8+ years of progressive accounting experience
• Experience leading month-end and year-end close processes
• Strong knowledge of GAAP and financial reporting
• Experience managing accounting operations within a multi-entity organization
• Experience leading or mentoring accounting staff
• Audit Experience

Preferred

• CPA license
• Experience in healthcare, insurance, SaaS, or venture-backed companies
• Experience with acquisitions, equity transactions, and complex accounting matters
• Experience implementing or improving accounting processes and internal controls
• Experience leveraging AI tools for productivity in finance/accounting function

Skills & Attributes

• Hands-on leader who enjoys owning both strategy and execution
• High attention to detail with exceptional organizational skills
• Strong analytical and problem-solving abilities
• Excellent written and verbal communication skills
• Comfortable working in a fast-paced, entrepreneurial environment
• Able to manage multiple priorities across several businesses simultaneously
• High degree of ownership, accountability, and integrity
• Continuous improvement mindset with a passion for building scalable processes

Benefits

• Work on meaningful projects that improve healthcare and employee benefits
• Competitive salary and equity opportunity
• Flexible work hours and remote-first environment
• Collaborative, entrepreneurial culture with significant ownership and autonomy
• Opportunity to help build and scale a growing portfolio of companies alongside experienced leadership
• Three weeks (15 business days) paid vacation time off
• Nine paid holidays
• Employer-paid health benefits for employee and family members