Role: Controller

Location: Chicago, IL (On-site; not remote. Candidate must be based in Chicago or willing to relocate within 90 days.)

Salary: $120K – $150K base + performance bonuses ($25K–$75K), profit share, and equity participation

About our client:

Our client is a pre-seed fintech startup building an AI-powered “Succession-as-a-Service” platform to help small business owners transition ownership. They are addressing the significant challenge of business succession for millions of American small businesses owned by Baby Boomers. Their leadership comes from backgrounds in M&A, technology startups, and small business operations. The company is rapidly expanding with a mission-driven approach to preserving entrepreneurship and building generational wealth.

Position Overview:

They are seeking a Controller who thrives on transforming financial chaos into clean, scalable operations. This person will be the operational backbone of their Fractional CFO Services practice—migrating messy QuickBooks Desktop files to cloud platforms, implementing GAAP-compliant processes, and building the financial infrastructure that supports rapid growth.

This is not traditional accounting; it is financial architecture for an AI-native fintech disrupting a massive market.

Key Responsibilities:

• Financial Transformation (60%)
• Lead QuickBooks Desktop → Online migrations with 30-day GAAP-compliant close cycles
• Convert cash basis accounting to accrual methodology for reporting accuracy
• Implement modern chart of accounts optimized for M&A readiness
• Execute month-end close processes across multiple client portfolios
• Maintain GAAP compliance while adapting to small business realities
• Strategic Advisory & Value Creation (25%)
• Provide fractional CFO services including budgeting, forecasting, and cash flow management
• Support M&A due diligence with organized financial documentation
• Drive EBITDA improvement initiatives and enterprise value optimization projects
• Prepare investor-ready statements, dashboards, and reporting
• Collaborate on transaction readiness assessments and buyer Q&A
• Process Documentation & AI Integration (15%)
• Document all financial workflows and procedures for AI automation initiatives
• Partner with product/engineering to standardize processes
• Build scalable operational frameworks for 10x client growth
• Create SOPs and training materials for the CFO Services practice

Qualifications:

• Technical Requirements:
• 2+ years QuickBooks Desktop → Online migration experience
• Proven data cleanup & chart of accounts optimization
• Advanced QB Online proficiency (third-party integrations, automation setup)
• GAAP compliance expertise in small business contexts
• Strong background converting cash → accrual accounting
• Month-end close optimization with documented process improvement
• Experience:
• 3–7+ years in small business or industrial accounting (manufacturing, construction, distribution preferred)
• Fractional accounting or consulting experience a plus
• M&A transaction exposure preferred but not required
• CPA strongly preferred

What they offer:

• Base salary: $120K – $150K (experience-based)
• Performance bonuses & profit share: $25K–$75K
• Equity participation tied to Series A and beyond
• Professional development: conference & continuing education support