Wintrust Asset Finance: Clearing the Way For Employees To Thrive

by Jan/Feb 2024

Kirk Phillips,
President and CEO,
Wintrust Commercial Finance


By nature, Wintrust has a very flat organizational structure, so the company endeavors to push leadership and decision-making down to the individual business unit level. The closer leaders are to their teams, the more effective communication, decision-making and collaboration become. This approach has the ability to empower individuals to make real-time decisions that meet clients’ ever-changing needs while still meeting organizational goals and requirements.

Wintrust Asset Finance (WAF), the holding company for Wintrust’s equipment-focused leasing and loan activity, has a multi-pronged market strategy with three specialized collaborative teams, focusing on specific market areas and client requirements.

Kirk Phillips, president and CEO of one of WAF’s divisions, Wintrust Commercial Finance (WCF), emphasizes trust in his leadership style, believing that people follow who they know they can trust.

“Your people listen to what you say, but, more importantly, they watch for your actions. These must be in alignment; otherwise, trust is lost,” Phillips says.

Trust is one of five leadership traits Phillips believes a great leader should exemplify; the others are transparency, clarity, empathy and consistency. He also believes that effective leadership delivers organizational results that represent the collective effort of the team as a whole.

At Wintrust, it’s apparent when leaders have done their job well, as Phillips encourages his leadership philosophy: “I’ve done my job when you don’t need me anymore.” This means Wintrust has the right people in the right positions, and those employees have the tools and training needed to effectively do their jobs. Wintrust empowers employees with appropriate levels of decision-making and authority from leaders without the looming effects of micromanagement.

“From there, my job is to clear the obstacles and get out of the way,” Phillips says. This allows the team at Wintrust to push the decision-making down to the front lines, where employees are actively interacting with internal and external clients. It allows for more creative thinking and quicker action.

“If all decisions have to come through one person, then the ultimate success of the organization is dependent solely on that person’s abilities – but if everyone is empowered to make decisions and take actions, then the growth of the overall organization is unlimited,” Phillips says. He believes this has translated to eight straight years of increasing financial success not only for the Wintrust Commercial Finance team, but for the individuals within the team. “We have a number of people who have steadily advanced throughout the organization because of their skills and decision making on the front lines.”

Wintrust is constantly looking for ways to develop its team members. The company has robust training and development programs for those who want to take their careers to the next level. Wintrust also encourages team members to get involved in external development activities, whether through professional accreditations, industry-specific events and activities or through mentoring programs. Wintrust strives to create an environment in which leaders can identify high performers who want to take the next steps and move into leadership position by giving them the opportunity to not only learn new skills, but also put them in practice. “Effective leadership is a learned skill that takes time and nurturing, and we strive to provide that at WCF,” Phillips says. •

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