Kirk Phillips -   “A Lesson in Persistence” President and CEO of Wintrust Commercial Finance (“WCF”), a subsidiary of Wintrust Financial Corporation, a $43 billion publicly traded bank holding company traded on the Nasdaq.


One of the objectives of Leasing Avenues is to bring you casually, up close, and personal video interviews with fascinating people in our industry (or outside) that through sheer force of will, passion, and intellect, defied the status quo and created something new!  Kirk’s story is inspiring, that it can be done!

Part 1:  Introduction to Kirk Phillips, CEO of Wintrust Commercial Finance

Kirk describes his circuitous path to entering the equipment leasing and finance industry.

Part 2: Genesis of Wintrust Commercial Finance

The path to Wintrust.  In 2014, Kirk and his team saw an opportune market and developed a model/business plan to start a business that addressed the opportunity.  Five years from a dead start, Kirk and his team of 49 (half of which are sales) are projecting ending 2020 with over a Billion in assets and originating over $700 Million.

Part 3:  From Vision to Reality

Kirk expands a small footprint bank (Chicagoland) nationally serving middle-market mid-large ticket to small ticket platform.  Some things were envisioned originally by Kirk, while others were expansionary opportunities that presented themselves.

Part 4: Key Takeaways From The Journey

Kirk and his team took 32 swings to connect finally.  While that is not the definition of “success” in baseball, it sure was in Kirk’s case. What did it take to get there, and were there doubts?

Kirk Phillips

Kirk Phillips Bio