Tech-Forward Bookkeeper / Fractional Controller for Multi-Entity Business (Digits AI)

About the Business: We are a growing, multi-entity business portfolio encompassing multi-state franchise operations (salon suites in Colorado and Florida) and commercial/residential real estate development (including a newly launched multi-unit project). We are transitioning away from a traditional legacy accounting firm and modernizing our entire financial stack to be AI-native. The Role: We are seeking a highly autonomous, tech-savvy bookkeeper or fractional controller to lead our migration to Digits AI and manage our ongoing financial operations. This is not a manual data-entry position. Because the AI platform will handle the heavy lifting of routine transaction categorization, your primary value will be in system setup, training the AI, managing complex multi-entity consolidations, and providing clear, actionable financial reporting. Key Responsibilities: System Migration & AI Training: Lead the transition to Digits AI, set up automated bank feeds, and establish custom vendor rules to train the platform's categorization models. Multi-Entity Management: Maintain clean, separate books for distinct LLCs (franchise operations vs. real estate development) while accurately tracking intercompany transfers and shared expenses. Continuous Close & Review: Monitor the automated bookkeeping, stepping in to resolve flagged/ambiguous transactions and ensuring accurate month-end closes. Tech Stack Expertise: Must have experience with, or a strong aptitude for learning, modern AI accounting software (Digits AI experience is a massive plus, but experience with similar automated platforms like Ramp, Brex, or specialized continuous-close software is acceptable). Multi-Entity Experience: Proven track record of managing books for complex organizational structures (franchises, real estate development, or holding companies). Strategic Mindset: You treat bookkeeping as a strategic asset, not just a tax compliance chore. You look for ways to optimize workflows and reduce manual work. U.S. GAAP Knowledge: Strong understanding of U.S. accounting principles, particularly regarding capital expenditures, depreciation, and real estate development costs.