Kirk S. Phillips has built his career on collaboration, vision and a people-first approach to leadership. As President and CEO of Wintrust Asset Finance, he is most proud of helping initiate, launch and grow Wintrust Commercial Finance, a division of Wintrust Asset Finance, and its contribution to helping Wintrust Asset Finance become the 31st largest equipment finance and leasing company — and the 18th largest bank-owned leasing company — in the U.S. Phillips credits much of this success to a core strategy: building rather than buying. By hiring the right talent and empowering them to lead, Wintrust has expanded into small-ticket financing, via Wintrust Specialty Finance, Commercial Dealer Services, and renewable energy — all of which are thriving.
His leadership style has deepened over time, with an increasing focus on listening. “To me, a good leader is both present and available, listens more than he speaks and treats others like he wants to be treated,” Phillips says. In a rapidly changing industry, he actively seeks insights from across the organization to make informed, consensus-driven decisions.
To the next generation of leaders, Phillips offers practical advice: take risks, learn from setbacks and seek out mentors who can provide guidance. As he puts it: “There are immense opportunities arising every day just looking for the next generation of leaders to take the leap and seize the moment. Why shouldn’t it be you?”
