Wintrust Executive and Leadership Team

July, 2026

Leadership Overview

Wintrust has 9 executives leading key functions including finance, operations, technology, and marketing.

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

Leadership Roles at Wintrust

  • Chief Executive Officer, Wintrust Investments - James Corbett
  • SVP-Business Line Chief Financial Officer - Kyle Furry
  • Senior VP & Chief Financial Officer, Wintrust Asset Finance - Timothy Leksas
  • Executive Vice President & Chief Financial Officer - David Stoehr
  • Senior Vice President, Chief Operating Officer - Chris Maudlin
  • Chief Operating Officer & Market Head, Commercial Banking - Paul Carlisle
  • Senior Vice President, Chief Marketing Officer - Wendy Schenker
  • Executive Vice President & Chief Information Officer - Michael Ryan
  • Deputy Chief Information Officer - Damon Farthing
  • Executive Vice President & Chief Technology Officer - Deb Lefevre
  • James Corbett - Chief Executive Officer, Wintrust Investments

    James Corbett, the Chief Executive Officer, Wintrust Investments at Wintrust, leads the strategic direction and operational execution for the company's investment management division. This executive role involves overseeing all aspects of wealth management services, including investment advisory, trust and estate planning, and asset management for high-net-worth individuals and institutional clients. Corbett drives the growth and development of the investment platform, ensuring it aligns with Wintrust's core philosophy of combining community bank values with sophisticated financial products. The Chief Executive Officer, Wintrust Investments fosters a client-centric approach, emphasizing personalized service and tailored financial solutions. James Corbett's leadership is instrumental in expanding Wintrust's wealth management capabilities and reinforcing its position as a comprehensive financial partner. This role requires a deep understanding of capital markets and fiduciary responsibilities to deliver exceptional value and build long-term client relationships.
    James Corbett

    Kyle Furry - SVP-Business Line Chief Financial Officer

    Kyle Furry, the SVP-Business Line Chief Financial Officer at Wintrust, directs financial strategy and oversight for specific business lines within the organization. This role involves managing budgets, forecasting financial performance, and ensuring fiscal responsibility across multiple operational units. Furry's responsibilities extend to analyzing financial data to identify trends, risks, and opportunities that impact profitability and growth. The SVP-Business Line Chief Financial Officer collaborates with divisional leaders to align financial objectives with strategic goals, supporting the company's unique community banking model and specialty finance businesses. Kyle Furry's expertise is crucial in maintaining the financial health of diverse business segments, ensuring efficient resource allocation and driving sustainable revenue generation. This leadership position requires a deep understanding of financial markets and regulatory compliance within the banking sector, contributing directly to Wintrust's overall market position and operational efficiency.

    Timothy Leksas - Senior VP & Chief Financial Officer, Wintrust Asset Finance

    Timothy Leksas, the Senior VP & Chief Financial Officer, Wintrust Asset Finance at Wintrust, spearheads the financial operations and strategic planning for the asset finance division. This critical role encompasses managing the financial health of specialty finance subsidiaries, including commercial insurance premium financing and life insurance premium financing. Leksas oversees financial reporting, budgeting, and forecasting specifically for these niche market operations, ensuring alignment with Wintrust's broader financial objectives. The Senior VP & Chief Financial Officer, Wintrust Asset Finance works closely with operational teams to optimize financial performance and identify growth opportunities within the premium financing sector. Timothy Leksas's financial acumen is vital for navigating the complexities of specialized financial products and supporting the expansion of Wintrust's diverse service capabilities. This leadership function ensures the profitability and strategic development of Wintrust's asset finance portfolio, reinforcing the company's reputation for sophisticated financial solutions.

    David Stoehr - Executive Vice President & Chief Financial Officer

    David Stoehr, the Executive Vice President & Chief Financial Officer at Wintrust, holds ultimate responsibility for the company's financial health and strategic financial planning. This senior executive role encompasses overseeing all financial operations, including accounting, treasury, financial reporting, and capital management across Wintrust's diverse portfolio of community banks and specialty finance businesses. Stoehr guides the financial strategy to support organic growth and strategic acquisitions, ensuring robust fiscal discipline and compliance with regulatory requirements. The Executive Vice President & Chief Financial Officer plays a crucial role in managing investor relations and communicating financial performance to stakeholders. David Stoehr's financial expertise is fundamental to Wintrust's sustained success and its ability to navigate complex market dynamics. This leadership position ensures the financial integrity and strategic direction necessary for Wintrust to maintain its prominent position in the financial services industry.
    David Stoehr

    Chris Maudlin - Senior Vice President, Chief Operating Officer

    Chris Maudlin, the Senior Vice President, Chief Operating Officer at Wintrust, oversees the operational efficiency and effectiveness across various business functions. This leadership role focuses on streamlining processes, optimizing resource allocation, and ensuring the seamless execution of Wintrust's community banking model and specialty finance operations. Maudlin collaborates with department heads to implement best practices and drive continuous improvement throughout the organization. The Senior Vice President, Chief Operating Officer plays a key part in integrating new technologies and systems to enhance service delivery and operational scalability. Chris Maudlin's strategic oversight contributes directly to maintaining Wintrust's reputation for personalized service and local decision-making authority. This position is essential for managing the day-to-day operations that support Wintrust's growth and its commitment to providing comprehensive financial services while upholding its core values.

    Paul Carlisle - Chief Operating Officer & Market Head, Commercial Banking

    Paul Carlisle, the Chief Operating Officer & Market Head, Commercial Banking at Wintrust, directs both the operational strategy and market leadership for the commercial banking division. This dual role involves ensuring the efficient functioning of commercial banking operations while also driving market penetration and client acquisition within Wintrust's key geographic areas. Carlisle oversees the development and execution of strategies aimed at expanding the commercial client base and enhancing service offerings. The Chief Operating Officer & Market Head, Commercial Banking works to align operational processes with market demands, ensuring Wintrust provides tailored solutions to local businesses and professionals. Paul Carlisle's leadership is critical for fostering strong client relationships and driving revenue growth within the commercial sector, reinforcing Wintrust's commitment to community-focused banking. This position is vital for maintaining Wintrust's competitive advantage in the Chicago metropolitan area, southern Wisconsin, and northwest Indiana.
    Paul Carlisle

    Wendy Schenker - Senior Vice President, Chief Marketing Officer

    Wendy Schenker, the Senior Vice President, Chief Marketing Officer at Wintrust, directs all marketing initiatives and brand strategy across the organization. This leadership position involves developing and executing comprehensive marketing plans to enhance Wintrust's unique community banking model and specialty finance businesses. Schenker oversees market research, advertising, digital marketing, and public relations efforts designed to strengthen customer engagement and attract new business. The Senior Vice President, Chief Marketing Officer ensures consistent brand messaging that highlights Wintrust's commitment to personalized service and local decision-making. Wendy Schenker's strategic vision guides the promotion of Wintrust's diverse offerings, including wealth management and mortgage lending, across its geographic footprint in the Chicago metropolitan area, southern Wisconsin, and northwest Indiana. This role is essential for communicating the company's value proposition and reinforcing its reputation as a relationship-focused financial institution.

    Michael Ryan - Executive Vice President & Chief Information Officer

    Michael Ryan, the Executive Vice President & Chief Information Officer at Wintrust, directs the company's overall information technology strategy and infrastructure. This pivotal role involves overseeing the development, implementation, and maintenance of all technology systems that support Wintrust's community banking model and specialty finance businesses. Ryan is responsible for ensuring the security, reliability, and scalability of the IT environment, which is critical for enhancing customer experience and operational efficiency. The Executive Vice President & Chief Information Officer collaborates with business units to identify technology needs and drive innovation, including the enhancement of digital banking platforms. Michael Ryan's leadership ensures that Wintrust leverages technology effectively to maintain its competitive edge and deliver seamless financial services across its geographic footprint. This position is fundamental to the company's ongoing investment in innovative solutions and its commitment to preserving a personal touch through advanced technological capabilities.

    Damon Farthing - Deputy Chief Information Officer

    Damon Farthing, the Deputy Chief Information Officer at Wintrust, supports the Chief Information Officer in managing the company's technology infrastructure and strategic IT initiatives. This role involves assisting in the oversight of technology operations, ensuring the security and efficiency of systems that underpin Wintrust's community banking and specialty finance operations. Farthing contributes to the planning and implementation of technology solutions designed to enhance customer experience and support business growth. The Deputy Chief Information Officer works closely with IT teams to maintain system integrity and explore innovative technological advancements. Damon Farthing's collaboration with the CIO is essential for executing Wintrust's technology roadmap, which includes investments in digital banking platforms and other advanced solutions. This position reinforces the IT department's capacity to support Wintrust's commitment to personalized service through robust technological capabilities.

    Deb Lefevre - Executive Vice President & Chief Technology Officer

    Deb Lefevre, the Executive Vice President & Chief Technology Officer at Wintrust, leads the company's technology vision and execution, focusing on innovation and infrastructure development. This executive role involves guiding the strategic direction of technology across Wintrust, ensuring that systems and platforms support the unique community banking model and specialty finance businesses. Lefevre oversees the development and implementation of cutting-edge technological solutions that enhance operational efficiency and customer engagement. The Executive Vice President & Chief Technology Officer is instrumental in driving Wintrust's digital transformation efforts, including the enhancement of online and mobile banking services. Deb Lefevre's leadership ensures Wintrust remains at the forefront of technological advancement in the financial services sector, supporting its commitment to personalized service through sophisticated digital tools. This position is critical for maintaining Wintrust's competitive edge and future growth.

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    Frequently Asked Questions Regarding Wintrust Top Executives and Leadership Team

    Who leads Wintrust?
    Wintrust is led by James Corbett (Chief Executive Officer, Wintrust Investments), along with executives such as Kyle Furry (SVP-Business Line Chief Financial Officer) and Timothy Leksas (Senior VP & Chief Financial Officer, Wintrust Asset Finance).
    Who is part of Wintrust’s executive team?
    The executive team of Wintrust includes leaders such as James Corbett (Chief Executive Officer, Wintrust Investments), Kyle Furry (SVP-Business Line Chief Financial Officer), Timothy Leksas (Senior VP & Chief Financial Officer, Wintrust Asset Finance) 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 Chief Executive Officer, Wintrust Investments, SVP-Business Line Chief Financial Officer, Senior VP & Chief Financial Officer, Wintrust Asset Finance, Executive Vice President & Chief Financial Officer, Senior Vice President, Chief Operating Officer.