Kirk is President and CEO of Wintrust Asset Finance, encompassing Wintrust Commercial Finance, Wintrust Specialty Finance (small ticket equipment finance) and Wintrust Equipment Finance (bank product specialist and debt discounting). These three entities represent over $4.5 billion in total assets and 116 employees, and is ranked as the 18^th largest bank-owned leasing company (based on 2024 data). He joined Wintrust in 2015 as one of the founders of Wintrust Commercial Finance and served as president and CEO until his current appointment in 2025.

Kirk began his career as a national bank examiner for the Office of the Comptroller of the Currency (OCC).  Following the OCC, he joined the private sector and now has over 36 years of experience in the equipment leasing and finance industry with positions of increasing responsibility at ITT Commercial Finance, Transamerica Equipment Financial Services and AIG Commercial Asset Finance. He has held roles in credit underwriting, direct sales and executive management. He has been a speaker and moderator at ELFA, Marine Money International, Marine Money Offshore and Workboat conferences due to his expertise in maritime and offshore finance. He has been Chairman of the Financial Institutions Business Council Steering Committee and the ELFA LeasePAC, and has served on ELFA’s Membership Committee, Advocacy Committee, Board, as both a Director and Officer, as well as the Foundation’s Academic Outreach Committee. He is a regular attendee of Capitol Connections. He has been a Guest Lecturer and a member of the  Executive Advisory Board at the Nelson Rusche College of Business at Stephen F. Austin State University (SFASU), and has been a strategic advisor to HEROMakers, a nonprofit providing support for orphans located in Latin America. Kirk holds a BBA and an MBA in Finance from SFASU.