Role: Head of CFO Services (CFO Services Architect)

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

Salary: $180K

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:

The Head of CFO Services will architect and scale our client’s financial transformation practice — a “startup within a startup” — turning messy, owner-dependent financials into clean, scalable, and investor-ready operations. This role is both strategic and hands-on: building systematic QuickBooks migration workflows, productizing financial processes for future AI automation, and assembling a high-performing team of accountants and controllers. Reporting directly to the CEO and CFO, the Head of CFO Services will manage half of the company’s core business and play a pivotal role in achieving Series A readiness.

Key Responsibilities:

• Design and implement a repeatable CFO services practice, including GAAP-compliant month-end close and QB Desktop → Online migration processes
• Build financial dashboards, KPI reporting, cash flow forecasts, and advisory services for SMB clients
• Partner with product and engineering teams to document, automate, and scale manual workflows into AI-powered financial tools
• Hire, train, and manage a team (Staff Accountant, Controller, Bookkeeper) within 6 months
• Serve as a trusted advisor to Baby Boomer business owners, simplifying complex financial concepts and building strong client relationships
• Deliver revenue growth targets: $50K+ MRR from CFO services within 12–18 months
• Prepare the business for Series A fundraising by demonstrating scalable, repeatable financial service delivery

Qualifications:

• 5–10+ years of experience in financial advisory, accounting, or CFO services (fractional CFO, fintech, M&A advisory, or startup environment)
• Expertise with QuickBooks Desktop → Online migrations and GAAP-compliant financial reporting
• Proven ability to build scalable financial service delivery models (Pilot.com, Kruze Consulting, inDinero, or similar experience strongly preferred)
• Track record of systematizing processes and preparing them for automation/AI integration
• Team leadership experience: ability to hire, mentor, and manage accounting/finance staff
• Comfort working with traditional business owners and explaining financial concepts simply
• Entrepreneurial, resourceful, and motivated by equity upside in a high-growth environment
• CPA credential strongly preferred

What they offer:

• Highly competitive base salary ($180K)
• Target total compensation $300K–$350K (salary, bonuses, equity)
• Equity stake (0.5%–1.0% ownership at founder level)
• Deal bonuses (percentage of M&A transaction fees, avg. $500K per sale)
• Immediate client base (9+ active clients; revenue equivalent to $250K+ base)
• Budget and authority to hire your CFO services team
• Direct partnership with founders on a mission-driven team
• Opportunity to build a “Pilot.com-level” CFO services business inside a pre-seed rocket ship