Robert Cleary

Senior Director

Rob joined Fort Dearborn Partners 2012 and is primarily based in the restructuring group, where he helps stabilize financial and operational performance by developing and implementing comprehensive profitability and working capital plans. On a typical engagement, he will build integrated financial models to forecast the income statement, balance sheet, cash flow and lending compliance of clients for forebearance agreements or refinancing. He also prepares 13-week cash flow forecasts, borrowing base and other schedules to reassure creditors and investors that the company is solvent and addressing identified problems.  A business plan is developed and he assists in the implementation of cost-reduction initiatives, disposition of non-core assets, implementation of cash conservation strategies and the on-going communications process with the creditors and investors of the company.  Work is typically performed for business owners, management, private equity firms, banks and various types of lenders.

On investment banking engagements, he prepares financial models and information memorandums for debt and equity placements, handling all information requests and communications from potential lenders/buyers and assists in negotiations to close the transactions.

Rob is also a member of the valuation practice, preparing financial models and valuation reports for transaction and financing purposes.

Rob started his career in public accounting with McGladrey & Pullen, where he was a Supervisor in the Assurance Services practice, providing services to primarily middle market companies. In addition to performing audits; he also worked as a consultant with the FDIC as the receiver of failed institutions.

Contact Information

Direct: (312) 683-3640
Cell: (630) 347-2994

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  • Financial Advisory Services
  • Value Creation & Turnaround Consulting
  • Investment Banking
  • Valuation

Industry Experience

  • Automotive
  • Distribution
  • Food
  • Manufacturing
  • Ecommerce & Retail
  • Transportation & Logistics
  • Printing & Packaging


  • University of Iowa – BS, Accounting
  • Northern Illinois University – MA, Accounting

Certifications and Memberships

  • CPA
  • Association for Corporate Growth (ACG)
  • Secured Finance Network (SFN, formerly CFA)


FDP News

Sep - 20

Fort Dearborn Advises Motor Distributor

Fort Dearborn Partners served as a financial advisor for the refinancing of a $3.5M Line of Credit and $2.2M mortgage for a $20 million Illinois-based motor distributor coming... Read More

Sep - 20

Jim Sandberg Joins Fort Dearborn

Fort Dearborn Partners is pleased to announce that Jim Sandberg has joined the firm as a Senior Associate.

Read More

Jul - 20

Fort Dearborn Advises Private High School

Chicago, IL - Fort Dearborn Partners is pleased to announce that we served as exclusive financial advisor to a private high school for the refinancing of $13,000,000 in... Read More