Rob Winkelmann
Rob is CEO of the DiBari Group where he is responsible for managing the group’s Debt Advisory Services division and the Financial Insights Learning division. Rob joined the DiBari Group in 2006 as CEO responsible for overseeing operations of the Advisory Services Business which services both private and public companies in the technology and healthcare market segments.
Since joining, Rob has helped the company restructure its business model and create a channel centric market strategy leveraging venture capital and private equity investor partners. Rob is also Co-founder of Financial Insights, a learning company focused on providing business & financial literacy training to Fortune 1000 companies and the SMB market. Financial Insights curriculum is designed to improve the effectiveness of on boarding new employees, driving corporate alignment, and creating a differentiated sales methodology for engaging clients and channel partners.
Rob has spent over 19 years in the capital markets including commercial and corporate finance and venture lending. Prior to joining DiBari Group, Rob started the West Coast operations for two venture lending institutions: Charter Financial (acquired by Wells Fargo) and Oxford Finance Corporation (acquired by Sumitomo Corporation). Prior to that time, Rob worked at LaSalle National Bank/ABN AMRO in Chicago providing senior secured debt, tax-exempt bond financings and other structured finance vehicles to private, public and not-for-profit entities.
Rob has advised clients and structured debt capital financings for companies in the software, telecommunications & infrastructure, new media/multi media, healthcare and life science industry segments. Rob has lead learning seminars and sat on several industry panels for the capital markets.
Rob earned his BSBA in Finance from Washington University St Louis and completed his MBA at the J.L. Kellogg Graduate School of Management at Northwestern University with an emphasis in entrepreneurship and marketing.

“I was in the process of evaluating two terms sheets for debt financing which would be used to enhance our liquidity & fund our commercialization. However, after meeting with the DiBari team, I was convinced their experience and knowledge of the market could help me gain a better deal for the company - And that’s exactly what we got!"
“The DiBari team took the time to walk me through all the nuances of venture debt and then secure a variety of lending options. In the end, DiBari brought together a syndicate of bank financing and mezzanine debt that has provided the additional capital necessary to truly accelerate our business. DiBari exceeded all..."
“We were unsuccessful in our attempts to secure an acceptable financing option that would subordinate to our senior lender until we retained the DiBari Group. They introduced us to an expansive list of qualified lenders and helped us close on a mezzanine financing option with a lender that has been a perfect match for our capital..."
“I was not familiar with the DiBari Group and was introduced to them by one of our directors, who recommended them on the basis of work they had done for other companies in which his firm had invested. During our initial conference call with the DiBari team, I was impressed with their knowledge of..."
“We met with the DiBari Group based on a referral from one of our Investors. At that time, we had already established our debt financing goals and had identified several willing lenders, so we were uncertain whether we could gain meaningful additional value for a process that was well defined and already underway..."
“We were introduced to the DiBari Group from one of our investors. At first, I was reluctant to use their services since we already had a couple of financing options on the table and I personally had experience procuring debt capital in the past. I was surprised by the breadth and depth of the DiBari Group’s strategic process..."
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