Itch Entertainment Reports to: Founder / CEO About the Role We’re looking for a hands-on CFO to lead financial management across two ticketing businesses. You will own cash flow planning, budgets, commission oversight, financial reporting, and the systems that keep our finances accurate and organized. This role requires someone comfortable getting into the details—reviewing transactions, understanding how money moves, and making sure upcoming obligations are covered. You must be AI-forward. We want someone who actively uses AI and automation to improve financial processes and can show examples of systems they have implemented. Key Responsibilities Cash Flow & Treasury Maintain a clear daily view of cash balances across companies and bank accounts. Build and update a rolling 13-week cash flow forecast. Track incoming marketplace payouts against payroll, commissions, purchases, debt payments, and other obligations. Plan account funding and cash transfers so payments are covered when due. Identify potential shortfalls early and present practical options to the CEO. Keep transfers between companies properly documented and reconciled. Budgets & Financial Planning Build operating budgets for each company. Compare actual results against budgets and explain meaningful differences. Monitor expenses, profitability, and working capital needs. Evaluate the financial impact of hiring, spending, and growth decisions. Give the CEO clear recommendations backed by reliable numbers. Commissions, Payroll & Payments Own the accuracy of commission calculations and maintain documented commission rules. Review supporting sales, profit, refund, and adjustment data before commissions are finalized. Oversee payroll preparation, vendor payments, and payment schedules. Manage the payroll/finance specialist responsible for routine processing and transfers. Establish clear preparation, review, and approval procedures for payments. Ensure commissions and payments reconcile to financial records. Accounting & Reporting Oversee bookkeeping, bank and credit card reconciliations, and the monthly close. Produce timely profit and loss statements, balance sheets, and cash flow reports for each company. Track receivables, payables, loans, and credit card obligations. Work with external accountants on tax preparation and required filings. Build a concise financial dashboard showing available cash, upcoming obligations, margins, expenses, and forecasted cash needs. AI & Automation Identify repetitive financial tasks and implement reliable automation. Use AI to support transaction categorization, variance analysis, reporting, and forecasting. Automate commission workflows, reconciliation checks, and payment reminders where appropriate. Connect accounting, banking, payroll, and internal operating data to reduce manual entry. Work with developers to turn financial requirements into useful internal tools. Validate automated outputs and maintain appropriate access controls, review steps, and audit trails. Leadership & Collaboration Partner with the Director of Operations and company managers to obtain accurate financial inputs. Clearly define responsibilities across finance, payroll, bookkeeping, and operations. Hold a weekly financial review with the CEO covering cash, obligations, performance, and decisions needed. Translate financial information into clear actions for a founder-led business. Required Qualifications Experience leading finance as a CFO, Head of Finance, Controller, or similar senior role. Strong hands-on experience with cash flow forecasting, budgeting, accounting oversight, and financial controls. Experience managing multiple entities, bank accounts, and payment obligations. Experience overseeing payroll and commission-based compensation. Advanced spreadsheet skills and experience with accounting and reporting systems. Demonstrated use of AI and automation in real financial workflows. Ability to investigate discrepancies, verify data, and follow issues through to resolution. Strong communication skills and a high level of discretion with sensitive financial information. Willingness to personally handle detailed work while building scalable processes. Preferred Qualifications Experience in ticketing, marketplaces, e-commerce, or another business with high transaction volume. Understanding of payout timing, refunds, chargebacks, inventory commitments, and working capital. Experience with QuickBooks and tools such as ChatGPT, Claude, Power Query, Zapier, Make, or n8n. Familiarity with APIs, SQL, or working directly with developers. CPA, CMA, or a comparable qualification. What Success Looks Like in the First 90 Days A complete, verified schedule of financial obligations across both companies. Reliable daily cash visibility and a weekly updated 13-week forecast. Documented commission calculations and payroll review procedures. Consistent monthly reporting with reconciled accounts. Clear payment approval and account funding procedures. Priority manual workflows automated, with checks to verify accuracy. The CEO can see what cash is available, what is due, and what the business can afford. Please submit your résumé and a brief explanation of: Your experience managing cash flow and finances across multiple entities. A financial process you improved using AI or automation, including the tools used and the result. Your experience overseeing commissions and payroll. Your availability and compensation expectations. We’re looking for someone who can own the numbers, anticipate cash needs, and build better financial systems.