top of page
UMC at Mills Park-Street View-Large Format-21.4.14 (2).jpg
Darren Headshot 2023.jpg


Chief Financial Officer

Mr. Cunningham is the Chief Financial Officer for Upshot®.  He is responsible for leading all accounting, reporting, finance, information technology, payroll, and treasury operations for the firm.  Mr. Cunningham and his team lend support to investment due diligence and asset oversight.  He is also a member of Upshot's investment committee.  Mr. Cunningham is a CPA with over 25 years of experience that includes ten years as a CFO, construction, real estate and equipment finance, public and private accounting, hospitality, securitizations and the sale of an operating company and related real estate assets.

Prior to Upshot, Mr. Cunningham served as CFO for a large heavy civil site developer.  Prior to that he spent 9 years as CFO for a multi-site heavy commercial truck dealership and 12 years of increasing roles with a private equity sponsored, vertically integrated timeshare developer.  Mr. Cunningham began his career as an auditor for Deloitte.   He is a University of Central Florida graduate with a Bachelor of Science in Accounting and a member of the AICPA.

bottom of page