At CFO (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 CFO’ operating in the Financial Services space. If you think a CFO’ 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.
Luis Rivera
Partner and CFO of G Squared
Luis Rivera is a general partner and chief financial officer at G Squared. Most recently, Luis was a senior director for finance at Novanta and a finance director at Danaher Corporation. Prior to these, he served as a senior associate at KPMG US and controller at Dupont. Luis holds an MBA in finance from Washington University in St. Louis and BSBA in accounting from University of Puerto Rico-Mayaguez.
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About G Squared: G Squared is a growth stage venture capital firm that invests privately in today’s most dynamic companies.
Michael McFerran
COO, CFO, Treasurer and Executive Vice President. of Ares Management
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About Ares Management: Ares Management is a global alternative asset manager focusing on credit, private equity, and real estate.
Chad Feigel
CFO of CMT Capital Markets Trading
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About CMT Capital Markets Trading: CMT provides operational and financial support to proprietary trading outfits, privately owned businesses and venture capital startups.
Olibia Stamatoglou
Chief Financial Officer of Victory Park Capital
Olibia Stamatoglou joined VPC in 2019 and is the Chief Financial Officer. She oversees business and fund operations, including finance, compliance and accounting. Previously, Olibia Stamatoglou served as vice president of finance at Valor Equity Partners where she managed all firm and fund finance activities. Prior to Valor, she served as chief operating officer and chief financial officer of First National Assets, a specialty finance private equity group specializing in tax lien purchases and real estate owned ventures. She joined First National Assets from Aurora Investment Management where she progressed through several accounting roles. Olibia Stamatoglou was recognized as one of Crain’s Notable Women in Finance for 2019. Olibia Stamatoglou received a B.S. in accounting and finance from DePaul University. She is a registered Certified Public Accountant in the State of Illinois (inactive).
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About Victory Park Capital: Victory Park Capital Advisors focuses on providing privately negotiated debt and opportunistic equity solutions.

D. Craig Mense
Executive Vice President & Chief Financial Officer of CNA Insurance Company
Craig has overall responsibility for CNA’s Corporate Finance Department, which provides asset and capital management, financial planning and analysis, investor relations, treasury services, corporate accounting, financial reporting, corporate tax, ceded reinsurance, financial regulation, internal audit and compliance, corporate development, and shared services to the organization. He is also responsible for Enterprise Risk Management and CNA’s non-core operations which include Life & Group Operations and Global Resource Managers which oversees CNA Re and other run-off operations. Craig holds a bachelor’s degree in history from the University of Virginia and a master’s degree in accounting from Georgetown University. He is a Chartered Property Casualty Underwriter (CPCU).
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About CNA Insurance Company: CNA is an Insurance Company, selling insurance products and services.
Pete D’Arrigo
Chief Financial Officer of Envestnet
Pete D’Arrigo is the Chief Financial Officer at Envestnet.
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About Envestnet: Envestnet is a provider of technology-enabled investment and practice management solutions to financial advisors.

Jillian Sheehan
EVP & CFO of Textura
Mrs. Sheehan has more than 10 years of accounting experience. Prior to joining Textura she held accounting positions at Andersen LLP and Pasquesi Sheppard. Mrs. Sheehan is a Certified Public Accountant and an MBA graduate of DePaul University. The accounting experience and leadership that she brings to Textura has enabled her to build an accounting team capable of supporting Textura’s rapid growth and market expansion.
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About ArrowStream, Textura: Textura is an online collaboration platform for the construction industry.

Jillian Sheehan
EVP & CFO of Textura
Mrs. Sheehan has more than 10 years of accounting experience. Prior to joining Textura she held accounting positions at Andersen LLP and Pasquesi Sheppard. Mrs. Sheehan is a Certified Public Accountant and an MBA graduate of DePaul University. The accounting experience and leadership that she brings to Textura has enabled her to build an accounting team capable of supporting Textura’s rapid growth and market expansion.
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About ArrowStream, Textura: Textura is an online collaboration platform for the construction industry.

Bob Jacobson
CFO of Chaifetz Group
Bob Jacobson is the Chief Financial Officer of Chaifetz Group. He has served as Chief Financial Officer of ComPsych Corporation since 1996. At Compsych, Bob is responsible for all financial functions of the organization, including accounting procedures and controls, banking relations, insurance and treasury functions. Prior to Compsych, Bob served as Vice President Finance for Medical Management of America, Director of Accounting for Pittway Corporation and Controller for Pittway’s First Alert division. Bob began his career with Ernst & Young. Bob received a bachelor’s degree from Cornell University and master’s of business administration degree from the Booth School of Business at the University of Chicago. Bob is also a Certified Public Accountant.
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About Chaifetz Group: Chaifetz Group is a venture capital and private equity firm specializing in early- and mid-stage growth companies.

Joseph Chopp
Vice President and CFO of First Analysis
Joseph Chopp is a vice president and CFO coordinating financial administration of First Analysis and its private equity and venture capital funds. Prior to joining First Analysis in 1999, he spent nine years at Arthur Andersen LLP, most recently as a tax manager in the financial services area. He earned a J.D. and a master’s degree in tax law from DePaul University and a master’s degree in accounting science from the University of Illinois at Urbana-Champaign. He is a certified public accountant.
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About First Analysis: First Analysis is a venture capital investment company that offers equity research, investment banking, and sales and trading services.
Karina B. Stahl
Managing Director, Chief Financial Officer – Investment Funds of Monroe Capital
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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

Stephen H. Haworth
Chief Financial Officer of Flexpoint Ford
Stephen H. Haworth is a Principal and Chief Financial Officer of Flexpoint Ford. Prior to joining Flexpoint Ford, Mr. Haworth was a partner at the accounting firm of Ernst and Young LLP. Mr. Haworth began his career in 1985 in the Chicago office of Ernst and Young LLP. From 1992 to 1994 Mr. Haworth was a member of Ernst and Young’s National Tax Department in Washington D.C.
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About Flexpoint Ford: Flexpoint Ford is a private equity firm specializing in financial services and healthcare investments.

Jim Gabriele
Senior Managing Director, CFO of RJ O’Brien and Associates
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About RJ O’Brien and Associates: The oldest and largest independent futures brokerage and clearing firm in the United States.

Richard Roeske
Vice President, Interim Chief Financial Officer and Chief Accounting Officer of Kemper Corporation
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About Kemper Corporation: Kemper Corporation is a financial organization providing insurance and consumer finance solutions for individuals and small businesses.
Kevin M. Killips
Executive Managing Director & Chief Financial Officer of PrivateBancorp
Kevin M. Killips is Executive Managing Director and Chief Financial Officer for The PrivateBank. In this role, Killips is responsible for the financing planning, treasury, accounting, reporting and management functions for the Company. He also oversees comprehensive operations, including information technology. Killips most recently served as Senior Vice President, Chief Accounting Officer and Corporate Controller with Discover Financial Services since March 2008, responsible for comprehensive accounting, reporting, planning and tax functions. Prior to that, Killips worked for nearly 10 years at LaSalle Bank and its then-parent company, ABN AMRO, serving as Executive Vice President, North American Chief Accounting Officer and Corporate Controller. He also was director of Internal Audit, and then Vice President-Finance at Transamerica Corporation. Killips began his career at Ernst & Young, where he served from 1979-1993. Killips serves as vice chair of the Board of Trustees for Dominican University.
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About PrivateBancorp: PrivateBancorp as a Delaware corporation in 1989 to provide highly personalized financial services.
Michael Burdick
Founder, Chief Strategy Officer & Interim CFO of Paro
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About Paro: Paro is a startup that offers a curated professional services marketplace for finance professionals.
Karl Mueller
Senior Vice President and Chief Financial Officer of Old Republic International Corporation
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About Old Republic International Corporation: The Company is one of America’s 50 largest shareholder-owned insurance businesses.
Jason O’Reilly
COO/CFO of DrawBridge Lending
Jason O’Reilly is the COO and CFO at DrawBridge Lending.
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About DrawBridge Lending: DrawBridge offers a lending loans with no margin calls backed by Bitcoin holdings.
John Tinsley
Vice President & Chief Financial Officer of Hilco Merchant Resources
John has over 30 years of retail financial experience including 17 in the liquidation industry. Since joining Hilco in 2000, John has been an integral member of the HMR senior leadership team responsible for the management and execution of all accounting and financial operations/reporting functions in addition to personnel administration. John’s expertise is utilized in collaboration with members of the HMR executive team to develop and implement tools and strategies to maximize the recovery on a wide range of retail assets for HMR clients. John works closely with Hilco Global’s senior leadership and the HMR team to continually evaluate and optimize the operating performance of all HMR transactions. In addition to working with the senior executives at Hilco, he interacts with senior level retail executives, financial professionals, lawyers, turnaround/restructuring experts, and banking professionals. Prior to joining Hilco, he held various financial control positions, including Divisional Vice President of Financial Operations for Rich’s/Lazarus/Goldsmith’s, one of Federated Department Stores’ (now Macy’s) larger operating divisions. John is a graduate of Georgia State University.
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About Hilco Merchant Resources: Hilco Merchant Resources provides analytical, advisory, asset monetization, and capital investment services to the retail sector.
Kimberly Loftis
CFO of Blue Marble Payroll
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About Blue Marble Payroll: Blue Marble Payroll is an integrated payroll management solution that combines leading-edge technology with superior customer service.