Wintrust Asset Finance embodies the entrepreneurial spirit, showcasing resilience and adaptability through ever-changing economic conditions. The company specializes in equipment finance and leasing solutions, operating across three divisions: Wintrust Commercial Finance, Wintrust Specialty Finance and Wintrust Equipment Finance. These divisions have collectively propelled Wintrust to the 19th spot among U.S. bank-owned equipment finance entities, as noted in the Monitor Bank 50.
At its core, Wintrust Asset Finance prioritizes personalized client relationships. Business unit leaders are given the autonomy to adjust strategies in response to market demands while maintaining a steadfast focus on financial performance and portfolio quality. This client-centric approach ensures the company remains agile and aligned with market trends, delivering exceptional service alongside impressive growth.
Serve, Listen, Empower
Kirk S. Phillips, President and CEO of Wintrust Commercial Finance, underscores the importance of servant leadership, active listening and empowering teams. “Great leaders excel at listening — both to their clients and their teams,” Phillips explains. He believes listening uncovers opportunities for innovation and improvement that might otherwise go unnoticed. Empowering teams with decision-making authority is another cornerstone of his philosophy, enabling collective success rather than relying on individual contributions.
Phillips emphasizes removing obstacles and providing teams with the tools to succeed. His “management by walking around” approach encourages direct engagement with employees and clients, offering unique insights into performance optimization. This hands-on leadership style fosters collaboration, trust and open communication.
Trust but Verify: The Autonomy Principle
Authenticity and empathy are pivotal to Phillips’ leadership ethos. He advocates for a culture where admitting mistakes and focusing on solutions build trust and inspire innovation. This philosophy aligns with his commitment to lifelong learning, which he nurtures through workshops, leadership programs and reading influential books like The 21 Irrefutable Laws of Leadership by John Maxwell.
Matching Style to Situation
Phillips’ leadership journey has evolved from micromanaging to empowering. Inspired by Ronald Reagan’s “Trust but verify” principle, he emphasizes setting clear goals and allowing teams the autonomy to achieve them. Periodic check-ins ensure alignment while post-project reviews provide opportunities for reflection and growth. These principles create a culture of accountability and continuous improvement where both leaders and teams can thrive.
Leadership Development is Key
Wintrust’s commitment to nurturing future leaders is evident through initiatives like the STRIPES Leadership Program and ECornell’s High Performing Leadership Program. These programs provide team members with the resources and training to take on leadership roles, ensuring the company’s sustained growth. Additionally, Phillips actively brings in industry experts to host workshops, enhancing the knowledge and confidence of his team while fostering a culture of excellence.
Enjoy the Journey
One of Phillips’ most memorable leadership lessons came early in his career: “Don’t be a jerk.” This advice serves as a reminder to treat others with respect and to lead without ego. By empowering others and prioritizing collective success, Phillips has created a thriving culture of collaboration and innovation at Wintrust Asset Finance.
For aspiring leaders, Phillips advises embracing risks and leading with confidence even when feeling not fully prepared. He encourages studying successful leaders, learning from challenges and continually honing leadership skills. Above all, he stresses the importance of enjoying the journey, as leadership is an evolving process of reflection and growth.
Benchmarks for Success
Wintrust Asset Finance continues to set benchmarks for success in the equipment finance industry. By fostering a culture of empowerment, authenticity and innovation, the company remains a dynamic force, delivering exceptional results for clients and stakeholders alike. With a focus on collaboration and forward-thinking strategies, Wintrust is well-positioned to adapt to future challenges and seize new opportunities for growth.
“Great leaders demonstrate the skill of listening. They listen to clients and customers, employees, competitors, supporters and detractors. Great ideas come from all around us-all we need to do is listen. And that means “active” listening. Really hearing what the other person is trying to tell us before formulating a response. It also means that what we hear we may not agree with or be something we want to hear. Listening to differing opinions may uncover areas we have not considered, or gaps in our current thinking. Having respective and courteous debate oftentimes leads to better outcomes.”
Kirk S. Phillips
President and CEO
of Wintrust Commercial Finance
