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Meet the Oak Street® leadership team

Oak Street Funding was founded in June of 2003 under the leadership of Rick Dennen. We have provided hundreds of millions of dollars in capital to insurance professionals in 47 states and currently manage third-party niche loan portfolios for various multi-national banks through our subsidiary Oak Street Servicing. Oak Street has navigated through the extreme economic cycles that have transpired, all while growing and building a long term sustainable business. Click here to read more about our history.


Rick Dennen   

Rick Dennen: Chairman, President and CEO

Rick Dennen started his career over 22 years ago in public accounting for a Big Four Firm focusing on the manufacturing and financial services industries. He held various leadership positions including responsibility for growth and software development. In 2000, he entered the private sector as a limited partner in a venture fund. His primary responsibilities included developing and evaluating business plans and financial models, deal structuring, negotiation, and portfolio management.

In 2003, Rick was hired by Oak Street Mortgage to diversify their revenue stream focused exclusively on the mortgage business. During the first year, Rick led the effort to acquire a contingent debt collection Company. Over the next three years, he assisted in the transformation to a purchase debt company that went from 17 to 120 employees, from less than $100,000 of pre-tax earnings to over $9.2 million in its third full year and became recognized as an Inc 500 company. The 400% increase in profitability was due entirely to organic growth. Also in 2003, Rick wrote the business plan for Oak Street Funding and developed every aspect of the business including the sales and marketing channels, underwriting guidelines, proprietary software, and capital.

Rick has a strong record of starting up and turning around large businesses by significantly increasing profitability and enterprise business value.Rick received his Bachelor of Science Degree in Accounting and Master of Business Administration from Indiana University in Bloomington Indiana. Rick is licensed to engage in the business of insurance in the State of Indiana for Life, Accident & Health products and a licensed Certified Public Accountant in the State of Indiana.

Telephone: (317) 428-3800
Fax: (317) 428-5000

Todd Gray  

Todd Gray: Chief Financial Officer

Todd Gray is the chief financial officer for Oak Street Funding. He has more than 22 years of experience in strategic planning, business development, national account management, investor relations, mergers and acquisitions, finance, financial reporting and treasury activities.  In senior level roles such as president, head of personal and commercial Lines, chief financial officer and corporate treasurer, Todd helped a billion-dollar, publicly-traded specialty insurance company achieve dynamic growth and profitability in varying  markets.

Todd’s strong background has included oversight of SEC compliance, capital market initiatives, corporate reinsurance, as well as marketing, product management and distribution for a nationwide business offering of 20 distinct insurance products across multiple distribution channels. He also played a key role in orchestrating the eventual sale of his previous organization to Munich Re.  Todd started his career with a Big Four accounting firm.

An Indiana University graduate, Todd has a bachelor’s degree in business with a concentration in accounting and is a Certified Public Accountant. Actively involved in several professional associations, Todd also serves on a number of philanthropic boards.

Telephone: 317-428-5153
Fax:  317-428-5015

Alicia Chandler  

Alicia Mitchell Chandler: Chief Counsel

 Alicia Mitchell Chandler is Chief Counsel for Oak Street. As Chief Counsel, Alicia is a member of the management team and is responsible for managing legal services for Oak Street, including, but not limited to, negotiations, contracts, loan documentation, collections, litigation, and direction of work with outside law firms. Prior to joining Oak Street, Alicia was first an associate, and then became a partner, at a mid-size Indianapolis firm where her practice focused on commercial collections, federal and state court litigation, and real estate foreclosures. Alicia holds a Bachelor of Science degree from the University of Cincinnati and her Juris Doctor from the University of Cincinnati College of Law. Alicia is a member of the bar in Indiana, United States District Court for the Southern and Northern Districts of Indiana, United States Bankruptcy Courts for the Southern and Northern District of Indiana.

Telephone: (317) 428-3847
Fax: (317) 805-5197

Kathy Yeary  

Kathy Yeary: Executive Director of Customer Service and Human Resources

Kathy Yeary is responsible for the customer service and compliance department, which includes portfolio performance and customer satisfaction, and the human resources department. Kathy has over 22 years of insurance and financial industry experience. Prior to joining Oak Street, she served as the Vice President – Asset Management at a specialty finance company and in several financial and operating capacities at Conseco and GTE. Kathy holds a Bachelor of Science Degree in Business Administration from the University of North Carolina, Wilmington.

Telephone: (317) 428-3838
Fax: (317) 805-2714

David Christman  

David Christman: Chief Information Officer

David Christman has over 12 years of computer programming and data analysis experience, most of which were primarily focused on the insurance commission asset stream. At Oak Street, he is responsible for all aspects of the company’s IT infrastructure including networking, telephony, software development, and data analysis. Prior to joining Oak Street Funding, David developed a web based asset management system which is used to monitor the performance of insurance commission assets and to evaluate new acquisitions. David holds a Bachelor of Arts Degree in Computer Science from DePauw University.

Telephone: (317) 428-3811
Fax: (317) 428-5111

Bill Nicholson  

Bill Nicholson: Executive Director of Sales

Bill Nicholson is currently the Director of Sales for Oak Street and is responsible for the strategic development and expansion of the sales department. Prior to joining Oak Street in September 2009, Bill spent eight years on both active and reserve duty in the United States Marine Corp and brings over 13 years management experience in the financial services industry driving growth and profitable results for Beneficial, HFC, and HSBC Bank.

Telephone: (317) 428-3835
Fax: (317) 428-5195

Barry Kehl  

Barry Kehl: Director of Underwriting

Barry Kehl oversees Oak Street Funding’s commercial underwriting efforts by managing the credit approval process, determining lending policies, minimizing risk, and helping with strategic decisions and planning. With 16 years of experience and prior executive level leadership positions for banking and investment companies, Kehl has a rich financial services background.

Barry has successfully handled the performance, management and monitoring of a $700 million commercial loan portfolio, managed commercial credit underwriting, and worked with regulatory bodies to ensure compliance. Barry is a graduate of Indiana University with a bachelor’s degree in business and a master’s degree in accounting.

Telephone: (317) 428-3805
Fax: (317) 805-2769

Maranda Stars  

Maranda Stars: Controller

Maranda Stars is responsible for the accounting, finance and treasury functions at Oak Street Funding. Prior to joining Oak Street, Maranda was a Senior Auditor at Ernst & Young where she performed audits and quarterly reviews for SEC and Non-SEC clients in the retail, consumer products and utilities industries. She also developed client-specific audit programs to improve the audit efficiency and managed staff associates. A Certified Public Accountant, Maranda is a cum laude graduate of Butler University with bachelor’s and master’s degrees in accounting. 

Telephone: (317) 428-3845
Fax: (317) 805-2765

Sarah Turner  

Sarah Turner: Director of Corporate Development

Sarah Turner oversees human capital growth and development at Oak Street Funding, including recruiting, on-boarding, retention, and leadership training. In addition, she contributes in a project management role across departments. Sarah has over 14 years of business experience working for six years in public accounting and industry and eight years as a Senior Consultant providing Leadership Development Consulting and Executive Coaching services. Sarah holds a Bachelor of Science degree in Accounting and Economics from Ball State University, is a Certified Public Accountant, and has various certifications for training and development.

Telephone: (317) 428-3803
Fax: (317) 428-5010


Oak Street expands Strategic Markets teamOak Street® expands strategic markets team to address the demand for larger loans for agencies, program administrators, MGAs and more. Read more >

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