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Kyle Bolenbaugh has a wealth of work experience, beginning with their role as a Senior Analyst at Donaldson, Lufkin & Jenrette in 1997. Kyle then moved on to Chase in 1995 as an Analyst, where they analyzed transactions for both buy-side and sell-side advisory assignments. In 2000, they took on the role of Associate at Robertson Stephens Advisors LLC, followed by a similar role at Jordan Edmiston Group in 2002. In 2003, they became Vice President at Zuma Capital Partners, and then in 2004 they took on the role of Vice President at Lincoln International LLC, where they managed and executed sell-side M&A transactions and financial advisory assignments. Finally, in 2014, they became Vice President of the Midwest Region at pelotonRPM, where they helped clients use pelotonRPM's live video role play simulations to prepare their teams for important conversations.

Kyle Bolenbaugh received their Bachelor of Arts (B.A.) in Math & Economics from Hamilton College in 1995. Kyle then went on to pursue a Master of Business Administration (MBA) from The Tuck School of Business at Dartmouth, which they completed in 2000.