Accounting Manager​/Director - Real Estate

Director of Accounting/Accounting Manager

Chicago, IL | In-Office (Downtown / West Loop area)

A privately held, Chicago-based real estate owner/operator is seeking a hands-on Director of Accounting to lead and fully own the accounting function across a growing portfolio of commercial assets.

This is a senior, high-impact role for someone who enjoys being close to the work, managing real volume, and operating with a high degree of autonomy in a lean, entrepreneurial environment.

This position serves as the top accounting role within the organization and will assume full responsibility for day-to-day accounting operations across multiple properties and corporate entities. The role replaces a part-time structure and is designed for a true full-time leader who can both execute and improve.

This is not a layered or review-only seat. The right person will be comfortable rolling up their sleeves, prioritizing in a fast-moving environment, and steadily improving processes without over-engineering.

You’ll work closely with ownership, operations, and external partners while running the accounting function end-to-end.

• Monitor cash activity across numerous bank accounts and maintain daily visibility
• Post journal entries and transactional activity for multiple entities
• Manage high-volume AP and AR, including invoicing, payments, and collections tracking
• Handle deposits, ACH/wires, and bill pay activity within the property management system
• Maintain clean, well-organized financial records and documentation

• Prepare monthly financial statements and supporting schedules
• Complete bank and balance sheet reconciliations
• Record loan activity and reconcile related balances
• Calculate and record management fees, reimbursements, and intercompany items
• Prepare rent aging and ownership reporting
• Support cash planning and periodic distributions

• Assist with budgets, CAM reconciliations, and property-level reporting
• Coordinate 1099 preparation and support tax filings with outside advisors
• Manage real estate tax payments and annual compliance filings
• Support audits, refinancings, acquisitions, dispositions, and entity setup

• Own the accounting system as the system of record
• Maintain charts of accounts, bank setups, and entity structures
• Improve workflows where helpful while keeping things practical
• Provide ad hoc analysis and insight to leadership

This role will resonate with someone who:

• Has real estate accounting experience in a small-to-mid-sized environment
• Is comfortable operating as a department-of-one (at least initially)
• Thrives in high transaction volume and isn’t afraid of AP/AR work
• Is a self-starter who can prioritize, ask questions, and operate independently
• Prefers ownership and accountability over layers and bureaucracy
• Strong experience with Yardi (required)
• 7+ years of progressive real estate accounting experience preferred
• Experience managing multiple properties and entities simultaneously
• Comfortable owning close, reporting, cash, and compliance personally
• CPA is a plus, not a requirement
• Highly organized with strong follow-through
• In-office role in downtown Chicago
• Some flexibility after ramp-up
• Competitive base salary with performance-based bonus
• Direct access to ownership and senior decision-makers

This is a true ownership seat where accounting leadership directly impacts visibility, execution, and growth. The right person will have real autonomy, trust from leadership, and the ability to run the function the right way—without unnecessary layers or red tape.

If you enjoy being close to the business and owning outcomes, this role is worth a conversation.