Financial Systems Consultant: Cloud Migration & AP Automation (Real Estate/PE background)

Job Description We are a small, family-owned real estate investment firm looking for a hands-on consultant (CFO, COO, or Chief of Staff level) to modernize our financial operations in relation to a land development investment. We currently operate on a legacy, analog-heavy system and need an expert to lead our transition into a digitized, cloud-based environment. Our books are currently in good condition but are stored locally on Quicken Desktop. Furthermore, our accounts payable process is entirely manual: invoices are emailed, printed, manually approved via Word documents, and paid via paper checks before being filed in physical cabinets. We are looking for a strategist who can not only execute the migration but also design and implement a scalable, automated infrastructure for our accounts payable and ACH payments. Key Responsibilities •System Migration: Lead the migration of three years of historical data (dating back to 2023) from Quicken Desktop to a cloud-based solution (e.g., QuickBooks Online). • AP Workflow Automation: Design and implement a digital end-to-end workflow for accounts payable. We are looking to move away from paper checks and manual filing toward solutions like Bill.com, Ramp, or similar platforms. • Banking & Payments: Set up and optimize ACH payment processes to replace paper checks, where possible. • Strategic Advisory: Recommend best practices for modernizing a historically analog operation, specifically tailored to land development and private equity structures. • Project Management: Coordinate with our internal team, including the Analyst (primary POC), our existing Bookkeeper, and the Business Manager. Qualifications • Expertise in Financial Tech Stacks: Proven experience setting up and migrating to cloud accounting (QBO) and AP automation tools (Bill.com, Ramp, etc.). • Industry Experience: Direct experience in Real Estate Development, Private Equity, or Multi-Entity Accounting is highly preferred. • Consultative Mindset: You should be a systems-thinker who can suggest policies and workflows, not just perform data entry. • Modernization Specialist: Experience helping "analog" companies successfully navigate digital transformations. Project Scope & Timeline • Volume: We typically process 10–20 monthly bills from service providers and several large consultant invoices a quarter. We also handle periodic reimbursements. • Revenue Context: The investment is currently in a capitalization phase, with revenue expected to begin in 2026. • Deadline: We aim to have the new system fully operational by the end of Q1 2026. How to Apply Please provide a brief overview of your experience with similar cloud migrations and AP automation projects. Specifically, mention which software stacks you recommend for a real estate investment firm of our size and your experience with land development expenses, if relevant. Apply tot his job Apply To this Job