Director of Finance
Legacy Healthcare
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Job summary
Legacy Healthcare in Skokie, IL is seeking a hands-on Director of Finance to lead accounting, financial reporting, budgeting, and forecasting while supporting acquisitions and capital strategy.
The successful candidate will manage day-to-day accounting across multiple properties and entities, build scalable financial processes, and provide ownership with actionable insights to drive growth and value creation.
Qualifications
- Bachelor's degree in Accounting, Finance, or related field.
- 5-10 years in accounting, finance, financial reporting, or financial management.
- Experience in commercial real estate, real estate investment, or property management preferred.
- Strong understanding of accounting principles, financial statements, reconciliations, and month-end closing.
- Experience with budgeting, forecasting, cash flow analysis, and financial modeling.
- Ability to oversee a bookkeeper while reviewing financial results.
- Excellent communication with ownership and external partners.
Responsibilities
- Oversee accounting operations and ensure the accuracy of financial records.
- Supervise the bookkeeper and ensure transactions are recorded accurately and on time.
- Manage monthly, quarterly, and year-end closing processes.
- Review general ledger activity, bank reconciliations, AP/AR, and balance sheet accounts.
- Oversee accounting across multiple properties, legal entities, and real estate holding companies.
- Maintain appropriate accounting procedures, internal controls, and financial documentation.
- Coordinate with external accountants, tax advisors, and auditors.
- Identify opportunities to improve accounting systems, workflows, and financial processes.
- Own the preparation and presentation of monthly financial statements and management reports.
- Prepare and analyze income statements, balance sheets, cash flow statements, and property-level financial reports.
- Develop and maintain budgets, forecasts, cash flow projections, and financial models.
- Analyze actual results against budgets and forecasts, explain variances, and recommend corrective actions.
- Monitor property-level revenue, operating expenses, capital expenditures, debt obligations, and investment performance.
- Provide ownership with actionable financial analysis to support business decisions.
- Monitor liquidity, working capital, financial obligations, and capital requirements.
- Support the evaluation and acquisition of commercial real estate and other investment properties.
- Analyze acquisition opportunities, operating performance, projected cash flows, financing options, and potential returns.
- Build and review financial models for acquisitions, dispositions, refinancing, and property improvements.
- Assist with due diligence, including reviewing financial statements, rent rolls, operating expenses, leases, debt, and capital expenditure requirements.
- Evaluate investment assumptions and compare actual property performance against original underwriting.
- Work with ownership and other stakeholders to assess potential transactions.
- Identify opportunities to improve the financial performance of existing properties.
- Assist ownership with capital-raising initiatives and evaluate potential funding sources.
- Prepare financial analysis and materials for discussions with investors, lenders, and capital partners.
- Evaluate debt and equity financing alternatives for acquisitions and existing properties.
- Track investor capital contributions, capital calls, distributions, and related financial activity, as applicable.
- Assist with fund-level and investor reporting, financial models, and investment performance summaries.
- Monitor debt balances, loan covenants, maturity dates, interest expenses, and refinancing needs.
- Support the financial structuring and execution of acquisitions and other investment transactions.
- Work directly with company ownership on financial planning and strategic initiatives.
- Develop reporting tools and key performance indicators to improve visibility into company and property performance.
- Identify opportunities to improve profitability, cash flow, operational efficiency, and investment returns.
- Establish scalable financial processes as the real estate portfolio grows.
- Provide financial analysis and recommendations to support acquisitions, financing decisions, and long-term growth.
Skills
Education
Tools
Job description
Location: Skokie, IL
Job Type: Full-time
Work Arrangement: On-site
A growing real estate investment and property management company is seeking a hands‑on, detail‑oriented Director of Finance to oversee accounting, financial reporting, budgeting, and forecasting while playing an important role in acquisitions, financing, capital raising, and investment analysis.
This is an excellent opportunity for a finance professional who combines strong accounting fundamentals with an understanding of real estate investments and the financial decisions that drive business growth.
The Director of Finance will be responsible for ensuring the accuracy and integrity of the company's financial records, overseeing day‑to‑day accounting operations and bookkeeping, and delivering timely, meaningful financial reporting to ownership.
In addition to managing accounting and reporting, this individual will support real estate acquisitions, investment underwriting, fundraising, financing activities, and ongoing portfolio performance analysis.
The ideal candidate is comfortable working hands‑on with financial details while contributing to high‑level business and investment decisions. This person will work closely with ownership, oversee the bookkeeping function, and help build the financial infrastructure needed to support continued growth.
Oversee accounting operations and ensure the accuracy and completeness of all financial records.
Supervise the bookkeeper and ensure transactions are recorded accurately and on time.
Manage monthly, quarterly, and year‑end closing processes.
Review general ledger activity, bank reconciliations, accounts payable, accounts receivable, and balance sheet accounts.
Oversee accounting across multiple properties, legal entities, and real estate holding companies.
Maintain appropriate accounting procedures, internal controls, and financial documentation.
Coordinate with external accountants, tax advisors, and auditors.
Identify opportunities to improve accounting systems, workflows, and financial processes.
Own the preparation and presentation of monthly financial statements and management reports.
Prepare and analyze income statements, balance sheets, cash flow statements, and property‑level financial reports.
Develop and maintain budgets, financial forecasts, cash flow projections, and financial models.
Analyze actual results against budgets and forecasts, explain variances, and recommend corrective actions.
Monitor property‑level revenue, operating expenses, capital expenditures, debt obligations, and investment performance.
Provide ownership with actionable financial analysis to support business decisions.
Monitor liquidity, working capital, financial obligations, and capital requirements.
Support the evaluation and acquisition of commercial real estate and other investment properties.
Analyze acquisition opportunities, operating performance, projected cash flows, financing options, and potential returns.
Build and review financial models for acquisitions, dispositions, refinancing, and property improvements.
Assist with due diligence, including reviewing financial statements, rent rolls, operating expenses, leases, debt, and capital expenditure requirements.
Evaluate investment assumptions and compare actual property performance against original underwriting.
Work with ownership and other stakeholders to assess potential transactions.
Identify opportunities to improve the financial performance of existing properties.
Assist ownership with capital‑raising initiatives and evaluate potential funding sources.
Prepare financial analysis and materials for discussions with investors, lenders, and capital partners.
Evaluate debt and equity financing alternatives for acquisitions and existing properties.
Track investor capital contributions, capital calls, distributions, and related financial activity, as applicable.
Assist with fund‑level and investor reporting, financial models, and investment performance summaries.
Monitor debt balances, loan covenants, maturity dates, interest expenses, and refinancing needs.
Support the financial structuring and execution of acquisitions and other investment transactions.
Work directly with company ownership on financial planning and strategic initiatives.
Develop reporting tools and key performance indicators to improve visibility into company and property performance.
Identify opportunities to improve profitability, cash flow, operational efficiency, and investment returns.
Establish scalable financial processes as the real estate portfolio grows.
Provide financial analysis and recommendations to support acquisitions, financing decisions, and long‑term growth.
Bachelor's degree in Accounting, Finance, or a related field.
Approximately 5-10 years of relevant experience in accounting, finance, financial reporting, or financial management.
Experience in commercial real estate, real estate investment, property management, or a related industry strongly preferred.
Strong understanding of accounting principles, financial statements, reconciliations, and month‑end closing procedures.
Experience with budgeting, forecasting, cash flow analysis, and financial modeling.
Ability to oversee a bookkeeper while maintaining hands‑on responsibility for reviewing financial results.
Strong Microsoft Excel skills and experience with accounting software and financial reporting systems.
Ability to analyze financial information, identify discrepancies, and communicate findings clearly.
Strong organizational skills, attention to detail, and ability to manage multiple priorities.
Excellent communication skills and ability to work directly with ownership and external financial partners.
Experience managing accounting for multiple real estate properties, LLCs, or related legal entities.
Familiarity with commercial real estate acquisitions, underwriting, and due diligence.
Experience with real estate debt financing, refinancing, and lender reporting.
Exposure to private real estate funds, investor capital, fundraising, or investor relations.
Understanding of real estate investment metrics such as capitalization rates, IRR, equity multiples, and cash‑on‑cash returns.
CPA, CMA, or relevant graduate degree is a plus but not required.
We are looking for someone who is detail‑oriented, commercially minded, and proactive. The right candidate takes ownership of the numbers, maintains high accounting standards, and translates financial information into practical business insights.
This individual should be comfortable overseeing the day‑to‑day accounting function while participating in acquisitions, financing discussions, capital planning, and investment analysis. We value initiative, sound judgment, accountability, and the ability to work effectively in a growing, entrepreneurial real estate environment.
Direct interaction with company ownership and involvement in important business decisions.
Exposure to the full real estate investment lifecycle, from acquisition and financing through ongoing operations and portfolio performance.
Ownership of financial reporting, accounting processes, and forecasting.
The opportunity to contribute to investment decisions and company growth.
A hands‑on environment where initiative and process improvements make a measurable impact.
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