Carolynn Caruso joins STRIPES Leadership Program as senior vice president of sales and program leader. In this newly created role, Caruso will lead sales and marketing initiatives, oversee program operations and curriculum development and be responsible for growing enrollment.
Caruso is a transformational leader, cultural creator and strategic advisor with over 15 years of experience supporting founders, executives and high-performing teams across the beverage, UHNW family office, residential construction and private equity sectors. She has held leadership roles at Bai Brands, Crook & Marker and within the Office of Ben Weiss, where she drove strategy, operational execution and cross-functional alignment.
Caruso began studying and facilitating transformational leadership and personal development at age 21, spending nearly two decades immersed in this work. She built her expertise through intensive practice, live coaching and advanced training in human behavior and group dynamics. Known for stepping into leadership long before titles followed, Caruso brings a grounded, self-initiated approach that gives her a competitive edge in training, facilitation and transformational leadership. She joins STRIPES committed to building conscious, high-performing individuals.
“With her extensive background in sales and transformational leadership, Carolynn is an outstanding addition to our team,” Lisa Rafter, founder and CEO of STRIPES, said. “We’re thrilled to welcome her on board — she shares our passion for empowering leaders and the lifelong learner in all of us.”
“I’m truly honored to join STRIPES Leadership Program and fuel its inspiring mission of shaping the best and brightest of equipment finance leaders,” Caruso said. “I’m thrilled to grow its reach and impact with a team so passionate about creating real change in this industry.”

