Wintrust Executive and Leadership Team

July, 2026

Leadership Overview

Wintrust has 10 executives leading key functions including finance, marketing, technology, and operations.

Driven by a unique community banking model, Wintrust is dedicated to delivering personalized service and local decision-making authority, differentiating itself from larger banks through its commitment to community involvement and relationship banking.

Leadership Roles at Wintrust

  • Co-Chief Executive Officer, Private Client - Timothy Hannahs
  • Chief Executive Officer, Wintrust Investments - James Corbett
  • Chief Financial Officer - Richard Wickel
  • SVP-Business Line Chief Financial Officer - Kyle Furry
  • Executive Vice President & Chief Financial Officer - David Stoehr
  • Senior Vice President, Chief Financial Officer - Mortgage - Robert Truitt
  • Senior Vice President, Chief Operating Officer - Chris Maudlin
  • Senior Vice President, Chief Marketing Officer - Wendy Schenker
  • Deputy Chief Information Officer - Damon Farthing
  • Executive Vice President & Chief Technology Officer - Deb Lefevre
  • Timothy Hannahs - Co-Chief Executive Officer, Private Client

    Timothy Hannahs, the Co-Chief Executive Officer, Private Client at Wintrust, leads the strategic direction and operational management of the company's private client services. This executive role involves overseeing wealth management, trust services, and investment advisory functions, ensuring the delivery of sophisticated financial solutions tailored to high-net-worth individuals and institutional clients. Hannahs drives initiatives to expand the private client division's market reach and enhance client relationships through personalized service and expert financial guidance. The Co-Chief Executive Officer's responsibilities include fostering collaboration among wealth management teams, optimizing service delivery, and ensuring compliance with industry regulations. By focusing on the unique needs of private clients, Timothy Hannahs contributes significantly to Wintrust's reputation for combining community bank values with advanced financial products and technology. This leadership ensures the continued growth and success of Wintrust's wealth management offerings.

    James Corbett - Chief Executive Officer, Wintrust Investments

    James Corbett, the Chief Executive Officer, Wintrust Investments at Wintrust, directs the strategic vision and operational execution for the company's investment management division. This leadership role involves overseeing all aspects of investment strategy, portfolio management, and client services, ensuring the delivery of tailored investment solutions to a diverse client base. Corbett drives initiatives to enhance investment performance, expand market share, and foster strong client relationships through expert financial advice and personalized attention. The Chief Executive Officer's responsibilities include managing investment teams, developing innovative financial products, and ensuring compliance with regulatory standards. By leveraging Wintrust's robust infrastructure and commitment to relationship banking, James Corbett strengthens the company's position as a provider of sophisticated financial services. This executive's focus is on delivering exceptional value and achieving superior investment outcomes for clients.
    James Corbett

    Richard Wickel - Chief Financial Officer

    Richard Wickel, the Chief Financial Officer at Wintrust, directs the company's overall financial strategy and operations. This leadership role involves managing financial planning, budgeting, and forecasting to ensure fiscal health and support strategic growth initiatives. Wickel oversees the accounting department, treasury functions, and investor relations, ensuring accurate financial reporting and compliance with regulatory standards. The Chief Financial Officer's responsibilities extend to analyzing financial performance, identifying key trends, and providing actionable insights to drive profitability and operational efficiency across the organization. By collaborating with other senior leaders, Richard Wickel ensures that financial decisions align with Wintrust's community banking model and its expansion into specialty finance businesses. This executive's focus is on maintaining strong financial controls and optimizing capital allocation to support Wintrust's market position in the Chicago metropolitan area, southern Wisconsin, and northwest Indiana.

    Kyle Furry - SVP-Business Line Chief Financial Officer

    Kyle Furry, the SVP-Business Line Chief Financial Officer at Wintrust, provides dedicated financial leadership and strategic oversight for specific business lines within the organization. This role involves managing the financial planning, analysis, and reporting for designated segments, ensuring alignment with Wintrust's overall financial objectives and community banking model. Furry collaborates closely with business line leaders to drive profitability, optimize resource allocation, and identify opportunities for growth and efficiency. The SVP-Business Line Chief Financial Officer's responsibilities include developing financial forecasts, monitoring key performance indicators, and providing critical insights to support strategic decision-making. By focusing on the unique financial dynamics of each business line, Kyle Furry contributes to the sustained success and expansion of Wintrust's diverse portfolio, which includes community banking and specialty finance operations. This executive ensures financial discipline and strategic financial management across the company's operations.

    David Stoehr - Executive Vice President & Chief Financial Officer

    David Stoehr, the Executive Vice President & Chief Financial Officer at Wintrust, directs the company's comprehensive financial strategy, encompassing all aspects of financial planning, management, and reporting. This pivotal role involves overseeing the treasury, accounting, and financial operations to ensure the fiscal health and sustainable growth of Wintrust's unique community banking model and specialty finance businesses. Stoehr is responsible for managing capital allocation, risk management, and investor relations, providing critical financial insights to support strategic decision-making across the organization. The Chief Financial Officer's leadership ensures adherence to regulatory requirements and drives initiatives aimed at enhancing profitability and operational efficiency. By maintaining robust financial controls and fostering strong relationships with stakeholders, David Stoehr plays an integral part in Wintrust's expansion and its reputation for delivering personalized service and local decision-making authority throughout the Chicago metropolitan area, southern Wisconsin, and northwest Indiana.
    David Stoehr

    Robert Truitt - Senior Vice President, Chief Financial Officer - Mortgage

    Robert Truitt, the Senior Vice President, Chief Financial Officer - Mortgage at Wintrust, leads the financial strategy and operations specifically for the company's mortgage lending division. This critical role involves managing financial planning, budgeting, forecasting, and reporting for all mortgage-related activities, ensuring profitability and compliance with industry regulations. Truitt oversees the financial performance of the mortgage business, identifying key trends and opportunities for growth and efficiency. The Chief Financial Officer - Mortgage's responsibilities include managing capital, analyzing market dynamics, and providing strategic financial insights to support the expansion of Wintrust's mortgage origination and servicing capabilities. By ensuring sound financial management within the mortgage sector, Robert Truitt contributes to Wintrust's ability to offer comprehensive banking services and maintain its reputation for personalized service and local decision-making authority.

    Chris Maudlin - Senior Vice President, Chief Operating Officer

    Chris Maudlin, the Senior Vice President, Chief Operating Officer at Wintrust, oversees the day-to-day operational functions and drives efficiency across the organization's diverse business units. This executive role involves managing operational processes, optimizing resource allocation, and implementing strategic initiatives to enhance service delivery and customer satisfaction. Maudlin collaborates with department heads to streamline workflows, improve productivity, and ensure seamless integration of Wintrust's community banking model with its specialty finance subsidiaries. The Chief Operating Officer's responsibilities include overseeing risk management, ensuring regulatory compliance, and driving operational excellence throughout the company's footprint in the Chicago metropolitan area, southern Wisconsin, and northwest Indiana. By focusing on operational effectiveness, Chris Maudlin supports Wintrust's commitment to personalized service and relationship banking, ensuring the company maintains its competitive edge and continues its growth trajectory.

    Wendy Schenker - Senior Vice President, Chief Marketing Officer

    Wendy Schenker, the Senior Vice President, Chief Marketing Officer at Wintrust, architects and executes comprehensive marketing strategies to enhance brand visibility and customer engagement. This role involves overseeing all aspects of marketing, including digital marketing, advertising, public relations, and market research, to support Wintrust's unique community banking model. Schenker directs campaigns that highlight the personalized service and local decision-making authority that define Wintrust's market differentiation. The Chief Marketing Officer's responsibilities include analyzing market trends and customer needs to develop targeted messaging that resonates with businesses, professionals, and families across the Chicagoland area, southern Wisconsin, and northwest Indiana. By fostering strong relationships with local communities, Wendy Schenker ensures marketing efforts reinforce Wintrust's commitment to community involvement and relationship banking. This executive drives initiatives to expand Wintrust's reach and deepen customer loyalty through innovative and effective communication channels.

    Damon Farthing - Deputy Chief Information Officer

    Damon Farthing, the Deputy Chief Information Officer at Wintrust, supports the strategic direction and operational execution of the company's technology infrastructure and digital initiatives. This leadership position involves collaborating with the Chief Information Officer to manage IT operations, cybersecurity, and the development of innovative technology solutions that enhance customer experience and operational efficiency. Farthing oversees the implementation of digital banking platforms and ensures the integration of advanced technological tools across Wintrust's community banks and specialty finance subsidiaries. The Deputy Chief Information Officer's responsibilities include managing IT projects, optimizing system performance, and ensuring robust data security to protect sensitive customer information. By driving technological advancements, Damon Farthing contributes to Wintrust's ability to offer sophisticated financial products while preserving its core philosophy of personalized service and community focus. This executive plays a critical part in maintaining Wintrust's competitive edge in the financial services sector.

    Deb Lefevre - Executive Vice President & Chief Technology Officer

    Deb Lefevre, the Executive Vice President & Chief Technology Officer at Wintrust, directs the company's technology vision and oversees the development and implementation of its technological infrastructure. This senior role involves setting the strategic direction for all technology-related initiatives, including digital transformation, cybersecurity, and data management, to support Wintrust's unique community banking model and specialty finance businesses. Lefevre is responsible for ensuring that Wintrust's technology platforms are robust, scalable, and secure, enabling the delivery of personalized services and sophisticated financial products. The Chief Technology Officer's purview includes managing the IT department, driving innovation in digital banking solutions, and ensuring compliance with industry regulations. By championing technological advancements, Deb Lefevre enhances operational efficiency and customer experience across Wintrust's service areas in the Chicago metropolitan area, southern Wisconsin, and northwest Indiana. This executive's leadership is crucial for maintaining Wintrust's competitive position and commitment to relationship banking.

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    Frequently Asked Questions Regarding Wintrust Top Executives and Leadership Team

    Who leads Wintrust?
    Wintrust is led by Timothy Hannahs (Co-Chief Executive Officer, Private Client), along with executives such as James Corbett (Chief Executive Officer, Wintrust Investments) and Richard Wickel (Chief Financial Officer).
    Who is part of Wintrust’s executive team?
    The executive team of Wintrust includes leaders such as Timothy Hannahs (Co-Chief Executive Officer, Private Client), James Corbett (Chief Executive Officer, Wintrust Investments), Richard Wickel (Chief Financial Officer) and other senior executives.
    How many executives does Wintrust have?
    Wintrust has 10 executives leading key business areas.
    What roles are included in Wintrust’s leadership team?
    The leadership team of Wintrust includes roles such as Co-Chief Executive Officer, Private Client, Chief Executive Officer, Wintrust Investments, Chief Financial Officer, SVP-Business Line Chief Financial Officer, Executive Vice President & Chief Financial Officer.