Fractional Controller / External CFO

# Fractional Controller / External CFO and Bookkeeper for Three Growing Businesses We are seeking an experienced, highly organized **fractional controller, external CFO, and hands-on bookkeeper** to oversee the financial operations of three related but distinct businesses: * **iTrip Colorado Springs** — vacation-rental and property-management operations * **Urbanscape LLC** — real-estate and short-/mid-term rental operations * **Oceanscape LLC** — ownership and operation of a large vessel used for hospitality, research, and related business activities This is a long-term, dedicated, part-time role. We are looking for someone who can initially help refine and strengthen our existing records and processes, then grow into a true **controller/comptroller** for the businesses. ## Current State of the Records The records are not in poor condition. We have been consistently tracking income, expenses, and receipts and have maintained a substantial amount of supporting documentation. However, because the businesses have grown and involve multiple entities, accounts, properties, platforms, vendors, and expense categories, the records now need a professional review and cleanup to ensure they are fully reconciled, consistently categorized, free of duplication, and ready for reliable management reporting and tax preparation. This is not a reconstruction project. It is a **refinement, reconciliation, and systems-improvement project**. ## What We Need The initial work will include: * Reconciling bank accounts, credit cards, payment platforms, and operating accounts * Reviewing and matching receipts to transactions * Identifying and resolving duplicate transactions, duplicate receipts, or duplicate expense entries * Confirming that expenses are allocated to the correct legal entity * Reviewing intercompany transfers, owner contributions, reimbursements, and distributions * Standardizing expense categories and accounting treatment across the three entities * Tracking expenses by entity, property, vessel, project, and operating category * Reconciling revenue received through property-management platforms, booking platforms, direct payments, and other sources * Identifying missing documentation or transactions requiring clarification * Establishing a consistent monthly reconciliation and closing process * Producing accurate, useful monthly financial reports * Coordinating with tax professionals and maintaining tax-ready records * Helping us understand cash flow, profitability, obligations, and operating performance across each business ## Important: We Will Not Use QuickBooks Please do not apply with a proposal centered on moving us into QuickBooks. We are intentionally seeking a different accounting and financial-management system. The successful candidate should be comfortable evaluating, recommending, implementing, or working within modern alternatives that support: * Multiple entities * Receipt capture and document matching * Bank and credit-card integrations * Property-, project-, or vessel-level tracking * Intercompany accounting * Approval workflows * Reliable financial reporting * Automation without sacrificing accuracy * Collaboration among ownership, accounting staff, tax professionals, and operational team members Experience with Xero, Zoho Books, Sage, NetSuite, Wave, REI Hub, property-management accounting systems, or comparable platforms is helpful. We are open to recommendations, provided the system fits the businesses rather than forcing the businesses into an unsuitable structure. ## The Role Over Time The initial phase will focus on reviewing the existing books, completing reconciliations, resolving inconsistencies, confirming balances, and establishing standardized accounting procedures. Once that work is complete, the position will transition into ongoing controller-level responsibility, including: * Weekly transaction review and reconciliation * Monthly close * Accounts-payable and cash-flow oversight * Budgeting and forecasting * Entity-level and consolidated reporting * Expense review and cost-control recommendations * Identification of unusual transactions or financial risks * Documentation of accounting procedures and internal controls * Coordination with our CPA and tax preparers * Preparation of management reports explaining where money is coming from, where it is going, and what requires attention * Supporting informed financial and operational decision-making We do not need someone who merely categorizes transactions and generates generic reports. We need someone who will understand the businesses, investigate discrepancies, identify opportunities for improvement, and take ownership of the accuracy and usefulness of the financial records. ## Ideal Candidate You may be a strong fit if you have: * Significant bookkeeping, accounting, controller, or fractional-CFO experience * Experience managing accounting for multiple related legal entities * Strong reconciliation, review, and process-improvement skills * Experience identifying duplicate, missing, misclassified, or intercompany transactions * Experience with real estate, short-term rentals, property management, hospitality, marine operations, or other operationally complex businesses * The ability to create practical financial controls and repeatable processes * Strong spreadsheet and financial-reporting skills * Excellent attention to detail * The confidence to flag inconsistencies and request clarification when needed * The ability to communicate financial information clearly and practically * High standards for confidentiality, accuracy, responsiveness, and follow-through CPA, CMA, accounting-degree, controller, or CFO experience is preferred but not mandatory if you have substantial relevant experience and can demonstrate excellent work. ## Engagement This is a **dedicated, ongoing, part-time position**, not a short-term freelance assignment. The workload will likely be somewhat heavier during the initial review, reconciliation, and systems-improvement phase. After that, we expect a consistent weekly commitment and a structured monthly close. We want someone who has sufficient availability to treat these businesses as an important, continuing client and who is interested in becoming a trusted long-term financial partner. Please provide your proposed hourly rate or monthly retainer structure. We are open to beginning hourly during the initial review phase and transitioning to a monthly retainer once the workload becomes predictable. ## To Apply Please answer the following questions in your proposal: 1. What experience do you have reviewing and improving existing books that are generally well maintained but need stronger reconciliation and standardization? 2. Have you managed accounting for multiple related entities? How did you handle intercompany transactions? 3. What accounting platform would you recommend if QuickBooks is not an option, and why? 4. What experience do you have with property management, short-term rentals, real estate, hospitality, or marine businesses? 5. Describe a situation in which you identified duplicate, missing, or incorrectly classified transactions. 6. What does your monthly closing process normally include? 7. What reports would you provide to an owner who wants to understand cash flow, profitability, liabilities, and operating performance? 8. How many hours per week can you consistently dedicate to this engagement? 9. Are you willing to perform detailed receipt matching, reconciliation, and transaction review as part of an ongoing controller-level role? 10. Please provide an example of how you improved a client’s financial controls, reporting, or decision-making. Please begin your proposal with the phrase **“THREE-ENTITY CONTROLLER”** so we know you have read the full posting. We are looking for a reliable financial partner who can build on the records and systems already in place, improve consistency and reporting, and ultimately become the person responsible for ensuring that our financial information remains accurate, current, and useful.