Head of CFO Services @ AI-Driven Investment Bank

Head of CFO Services @ AI-Driven Investment Bank

Join to apply for the Head of CFO Services @ AI-Driven Investment Bank role at Right Hand Talent

Location : Chicago, IL (In-Person, River North)

Our client is an AI-native financial advisory firm modernizing how industrial business owners prepare for succession. They help founders of $5M–$100M manufacturing, distribution, and construction companies clean up financials, unlock value, and achieve premium exits.

Backed by leading venture investors, they’ve scaled from $0 to $800K ARR in under a year and are preparing for Series A — building a next-generation “Succession-as-a-Service” platform that merges AI automation with human expertise.

Position Overview :

The Head of CFO Services will build and scale the firm’s financial transformation practice—a “startup within a startup” turning messy, owner-dependent financials into clean, scalable, investor-ready operations.

You’ll design systematic QuickBooks migration workflows, productize financial processes, and lead a growing team of accountants and controllers while working directly with founders and small business clients.

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 :

This is not a traditional accounting role — it’s for a financial architect who thrives on structure-building, problem-solving, and scaling new systems. The right person combines technical mastery with entrepreneurial drive and people leadership.

✅ You likely fit if you :

❌ This role is not for you if :

What they offer :

Interested?

If you’re reading this thinking “this is exactly me” , please DM us on LinkedIn! 🔗

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