Fractional CPA / Controller-CFO for Multi-Division Operating Company (AI-Forward)

Overview We're a multi-division operating company (B2B transport + delivery operations) looking for a hands-on, AI-forward CPA to own our accounting and provide controller/CFO-level financial guidance. This is an ongoing part-time engagement (~10–20 hours/month) with room to grow. We want someone who uses modern tools and AI to work efficiently — not someone billing hours for manual data entry. You'll be the financial backbone of the business: keeping the books clean, the cash visible, and management informed enough to make good decisions. What you'll do Monthly close, bookkeeping oversight, and financial statement preparation (P&L, balance sheet, cash flow) Cash flow forecasting and weekly cash management across multiple bank accounts Vendor payment management and prioritization Tax planning, compliance support, and coordination with our tax preparer Sales tax issue management and resolution Financial analysis and forecasting across two operating divisions Shareholder/investor reporting support Due diligence and transaction support as needed Strategic financial guidance, including during periods of financial pressure or restructuring Must-haves Active CPA license Demonstrated use of AI in your workflow (e.g., automating categorization/reconciliation, document extraction, forecasting models, reporting). Tell us specifically how you use it. Strong QuickBooks Online experience Multi-entity / multi-division accounting experience Cash flow forecasting and management experience Comfortable advising owners directly and communicating clearly with non-finance stakeholders Discreet and reliable with sensitive financial information Nice-to-haves Experience with companies that have navigated tight cash periods, restructuring, or turnaround Sales tax / multi-state compliance experience Experience supporting fundraising, investor reporting, or M&A/diligence Industry experience in logistics, delivery, transport, or regulated/cash-intensive businesses How to apply In your proposal, please include: Your CPA license status and state. A specific example of how you use AI tools in your accounting/finance workflow and the time it saves. A brief example of a cash flow or restructuring situation you helped a client navigate. Your typical availability and turnaround time. Your hourly rate (and any monthly retainer option).