Paul Cleary

Paul Cleary

President and Chief Operating Officer

Paul Cleary serves as President and Chief Operating Officer of Red Oak Capital Holdings, a Michigan-based firm that manages a vertically integrated private small-balance commercial real estate lending strategy that targets short duration commercial mortgage assets secured in a first lien position by income-producing properties. He is responsible for overall company operations, including managing finances, business partnerships, and funding opportunities, as well as overseeing and measuring the success of business and employee initiatives.

Paul brings nearly 25 years of national commercial real estate lending experience involving small-balance originations, construction loans, as well as a federally chartered credit union’s national CRE loan portfolio.

He most recently served as Senior Loan Originator at Parkview Financial, a national private mid-market commercial real estate lender. His role encompassed the development of lending operations to fuel growth and transform the business into an institutional caliber lender.

Prior to that he was the Chief Operating Officer at Money360, Inc. where he created and managed all lending policies and guidelines as well as development of operational tools and information systems to support lending operations. He designed, created, and implemented, with the Chief Technology Officer, a proprietary end-to-end web-based SaaS commercial loan origination and asset management system, which led to increased production efficiency by more than 50% and brought portfolio management capabilities up to industry standards. He has experience selecting and managing outside legal counsel for loan operations and created, with legal counsel, the entire set of loan documents that increased their efficiency and effectiveness for the company overall.

He earned a master’s degree in Business Administration from the University of California, Irvine, a juris doctor degree (JD) from the University of San Diego School of Law and a bachelor’s degree in Political Science from the University of California, Santa Barbara.