Right Hand Talent
Head of CFO Services @ AI-Driven Investment Bank
Right Hand Talent, Chicago, Illinois, United States, 60290
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:
Have 5–10+ years in financial advisory, accounting, or CFO services (fintech, M&A, or startup environment)
Are an expert in QuickBooks migrations and GAAP reporting
Have built scalable financial delivery models (Pilot.com, Kruze, inDinero, etc.)
Have led finance or accounting teams and enjoy building systems from scratch
Are entrepreneurial, hands‑on, and motivated by equity and impact
Hold a CPA credential (strongly preferred).
❌
This role is not for you if:
You have limited experience with QuickBooks or SMB financial operations.
You prefer narrow individual‑contributor work over team leadership.
You’re uncomfortable managing traditional business clients or owner‑dependent operations.
You need rigid structure, predictability, or corporate bureaucracy to thrive.
You’re focused on salary alone and not motivated by performance-based compensation or equity growth.
What they offer:
$150K–$180K base + 40–100% performance bonus
0.5%–1.0% equity ownership + deal bonuses on M&A transactions
Health stipend (70% coverage, up to $750/month), 20 PTO days + 11 holidays
Full authority to build and lead your own CFO Services team
Opportunity to play a key role in preparing for Series A and scaling AI-powered financial operations
Interested? If you’re reading this thinking
“this is exactly me” , please DM us on LinkedIn!
#J-18808-Ljbffr
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:
Have 5–10+ years in financial advisory, accounting, or CFO services (fintech, M&A, or startup environment)
Are an expert in QuickBooks migrations and GAAP reporting
Have built scalable financial delivery models (Pilot.com, Kruze, inDinero, etc.)
Have led finance or accounting teams and enjoy building systems from scratch
Are entrepreneurial, hands‑on, and motivated by equity and impact
Hold a CPA credential (strongly preferred).
❌
This role is not for you if:
You have limited experience with QuickBooks or SMB financial operations.
You prefer narrow individual‑contributor work over team leadership.
You’re uncomfortable managing traditional business clients or owner‑dependent operations.
You need rigid structure, predictability, or corporate bureaucracy to thrive.
You’re focused on salary alone and not motivated by performance-based compensation or equity growth.
What they offer:
$150K–$180K base + 40–100% performance bonus
0.5%–1.0% equity ownership + deal bonuses on M&A transactions
Health stipend (70% coverage, up to $750/month), 20 PTO days + 11 holidays
Full authority to build and lead your own CFO Services team
Opportunity to play a key role in preparing for Series A and scaling AI-powered financial operations
Interested? If you’re reading this thinking
“this is exactly me” , please DM us on LinkedIn!
#J-18808-Ljbffr