At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the Banking space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected].
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.

Michael Rose
Chairman, CEO & President of Metropolitan Capital
Michael P. Rose is Chairman, CEO and President of the Company, Chairman and CEO of the Bank, and Chairman, CEO and Principal of Metropolitan Capital Inc. Mr. Rose was formerly the Acting Executive Director (CEO) of the Illinois Housing Development Authority. Mr. Rose served previously as the Authority’s Staff Attorney, Legislative Liaison, General Counsel, Chief Development Officer and Deputy Executive Director. Subsequently, Mr. Rose was a Principal in, and helped to found, the Lexecon Strategy Group, a strategic consulting firm. At the Lexecon Strategy Group, Mr. Rose led the firm’s financial services practice and focused primarily upon the cross-selling of financial services.
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About Metropolitan Capital: Metropolitan Capital is a Universal Bank targeting entrepreneurs and the businesses they own and operate.

Michael O’Grady
President, Chief Executive Officer & Director of Northern Trust
Michael O’Grady is President of the Corporate & Institutional Services business unit at Northern Trust and serves as a member of the Corporation’s Management Committee. Northern Trust’s C&IS business unit is a leading provider of asset servicing, investment management, banking and related services to institutional clients worldwide including but not limited to corporate and public pension funds, sovereign wealth funds, supranational organizations, investment management firms, foundations and endowments, healthcare organizations, insurance companies, and other financial institutions. Prior to assuming his current role, Mike served as Executive Vice President & Chief Financial Officer of Northern Trust. Mike joined Northern Trust in 2011 from Bank of America Merrill Lynch, where he served as a Managing Director in the firm’s Investment Banking Group and head of the Depository Institutions Group for the Americas. He joined Merrill Lynch in 1992 as an Associate. Prior to Merrill Lynch, Mike worked for Price Waterhouse. Mike earned a BBA from University of Notre Dame and a MBA from Harvard Graduate School of Business. He is a board member of the Field Museum, the Museum of Contemporary Art and Catholic Charities.
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About Northern Trust: Northern Trust is a global leader in delivering innovative investment management, asset and fund administration, fiduciary and banking.

Theodore L. Koenig
Chairman & CEO of Monroe Capital
Theodore L. Koenig’s Role at Monroe Capital is President and Chief Executive Officer. He Joined the team: 2004. His Education: Kelley School of Business at Indiana University, B.S. in Accounting with high honors, Chicago-Kent College of Law, J.D. with honors. His experience:Hilco Capital LP, President and Chief Executive Officer, Holleb & Coff, Partner, Winston & Strawn, Associate
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About Monroe Capital: Monroe Capital is a provider of senior and junior debt and equity co-investments to middle market companies in the U.S. and Canada

Larry Richman
Senior Executive Vice-President and Group Head, CIBC US Region, and President and CEO, CIBC Bank USA of PrivateBancorp
Larry Richman is President and Chief Executive Officer of PrivateBancorp, Inc., and The PrivateBank, a wholly owned subsidiary of PrivateBancorp. Since assuming the leadership role at PrivateBancorp in November 2007, Mr. Richman has been directing the execution of a strategic plan designed to build the hometown Chicago bank of choice for middle-market commercial and commercial real estate companies, as well as business owners, entrepreneurs, executives and families.
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About PrivateBancorp: PrivateBancorp as a Delaware corporation in 1989 to provide highly personalized financial services.

Rick Burgess
CEO / Co-Founder of Connect Lending
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About Connect Lending: A marketplace connecting business and lenders across 42 different loan types

Alberto J. Paracchini
President & Chief Executive Officer of Byline Bank
More than a financial institution, we are a bank of people. Each of us is dedicated to rolling up our sleeves, and doing whatever it takes to get you what you need. To us, this is personal. It’s why we put our names behind everything we do as we deliver the personalized banking experience you and all Chicagoans deserve.
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About Byline Bank: Byline Bank provides personal banking and business banking services.

Rudy Trebels
President and CEO of Wedgewood Investment Group, LLC
Rudy Trebels is a professional focused on providing high-quality service and customer satisfaction in commercial real estate, equipment leasing ,and finance. During his 35 + year career in the finance industry he has completed over approximately $1BB in real estate transactions with over 100 different lenders and investors. As a leader in executive management positions he has gained the reputation of being an innovator, and provider of financing to thousands of companies across the United States. Rudy has a B.S. Degree in Business from Drake University , and has served on the Drake University Board of Trustees since 2004. Rudy serves on the finance, student life and audit committees. Rudy has been an active member of the Governing Board of Directors for Boys Hope Girls Hope of Illinois since 1997, and the recipient of the Heart of Gold Award in 2004. In addition to being a humanitarian, Rudy is an avid golf player, and a member of Bob O’Link Country Club.
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About Wedgewood Investment Group, LLC: Wedgewood Investment Group is an investment banking entity that offers its services for middle market companies.

Tom Paprocki
CEO of Ziegler
Tom Paprocki is chief executive officer of The Ziegler Companies, Inc., a multi-faceted specialty investment firm that serves the fields of healthcare, senior living, religion, and education. In his role, Tom leads the operations of the firm, with an emphasis on strategy, client relationships, and strategic plan execution. He is also a member of the Ziegler Board of Directors. Ziegler has successfully provided capital, corporate finance, money management and financial advice to individuals and institutions for over a century. Prior to being named CEO, Tom was president of The Ziegler Companies, Inc. and responsible for the Capital Markets and Wealth Management businesses, as well as Marketing Communications, Services & Technology and Human Resources. He joined Ziegler in 1997 as a senior vice president, overseeing taxable bond trading activities. Tom previously served as president of the Huntington Capital Group, a subsidiary of Huntington Bancshares. Prior to that, he was a senior vice president, head of Bond Trading and Fixed Income Research at Robert W. Baird & Co., Inc. Tom headed Ziegler’s business planning team in 2000 and has been instrumental in creating the firm’s current long-term business plan. He holds a B.S. in business administration and a M.S. in economics from Marquette University, Milwaukee, WI
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About Ziegler: Ziegler is a full-service, specialty investment firm and broker-dealer. We provide investment banking, sales & trading.
Kevin Werner
CEO of Renovo Financial
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About Renovo Financial: Renovo is the premier provider of financial and strategic support for real estate investors