Wintrust Executive and Leadership Team

Kendra Castelloni, the Co-Chief Executive Officer, Wintrust Private Client at Wintrust, directs high-net-worth wealth management initiatives across the Chicagoland area. Castelloni architects bespoke financial strategies, including trust planning and estate management, to support the complex needs of affluent families and institutional clients. By aligning private banking services with the broader community-focused model, the Co-Chief Executive Officer, Wintrust Private Client ensures that high-net-worth individuals receive personalized attention alongside institutional-grade investment advisory. This leadership role involves constant collaboration with the wealth management division to refine asset management offerings and retirement planning solutions. Through the expansion of private client services, Kendra Castelloni drives significant growth in the wealth management sector. Ultimately, Castelloni secures long-term client loyalty by maintaining the personal touch that defines the organization, ensuring that private banking remains a cornerstone of the overall financial holding company strategy.

Jim Corbett, the Chief Executive Officer, Wintrust Investments at Wintrust, directs the strategic vision and market performance of the investment division. Corbett architects comprehensive investment advisory services, including retirement planning and asset management, tailored to meet the specific goals of high-net-worth individuals and institutional clients. Overseeing the investment portfolio across the regional footprint, the Chief Executive Officer, Wintrust Investments ensures that all advisory activities align with the company's core philosophy of sophisticated financial solutions. This leadership role involves managing the division's growth through strategic market analysis and the deployment of innovative investment tools. By enhancing the wealth management platform, Jim Corbett directly impacts the company's ability to attract and retain sophisticated investors. Ultimately, Corbett secures the competitive position of the investment arm, ensuring that the division contributes significantly to the overall financial health and reputation of the organization.

Bob Truitt, the Senior Vice President, Chief Financial Officer - Mortgage at Wintrust, directs the financial planning, risk management, and capital allocation for the mortgage origination and servicing business. Truitt architects fiscal strategies that support the company's mortgage lending operations, ensuring profitability and regulatory compliance across the regional market. Overseeing the financial health of the mortgage division, the Senior Vice President, Chief Financial Officer - Mortgage ensures that lending activities remain aligned with the broader corporate risk appetite. This leadership role involves managing liquidity and capital requirements to support the high volume of mortgage originations. By optimizing the financial performance of the mortgage business, Bob Truitt directly impacts the company's ability to provide competitive lending solutions to families and professionals. Ultimately, Truitt secures the financial stability of the mortgage segment, ensuring that the division remains a key contributor to the organization's diversified revenue streams.

Rob Solem, the Senior Vice President, Chief Financial Officer Insurance Funding at Wintrust, directs the financial operations and strategic planning for the specialty insurance premium financing business. Solem architects robust financial models to manage the unique cash flow requirements of commercial and life insurance premium financing. Overseeing the fiscal performance of this specialty niche, the Senior Vice President, Chief Financial Officer Insurance Funding ensures that the division maintains strong margins while managing credit risk effectively. This leadership role involves coordinating with the broader finance team to ensure that insurance funding activities support the company's overall growth objectives. By optimizing the financial structure of the insurance premium financing business, Rob Solem directly impacts the company's ability to serve specific market niches with precision. Ultimately, Solem secures the profitability of the insurance funding segment, ensuring that this specialty business remains a vital component of the organization's diversified financial portfolio.

David Stoehr, the Executive Vice President & Chief Financial Officer at Wintrust, directs the overall financial strategy, capital management, and investor relations for the entire holding company. Stoehr architects the fiscal framework that supports organic growth and strategic acquisitions across the Midwest. Overseeing the financial reporting and treasury functions, the Executive Vice President & Chief Financial Officer ensures that the organization maintains a strong balance sheet and optimal capital structure. This leadership role involves constant collaboration with the Board and other C-suite leaders to drive long-term shareholder value. By managing the company's financial health, David Stoehr directly impacts the ability to invest in digital banking platforms and innovative solutions. Ultimately, Stoehr secures the financial integrity of the organization, ensuring that the company remains well-positioned to execute its mission of combining community bank values with sophisticated financial capabilities.

Kyle Furry, the SVP-Business Line Chief Financial Officer at Wintrust, directs the financial analysis and performance monitoring for specific business lines within the holding company. Furry architects detailed financial reporting systems that provide actionable insights into the profitability and efficiency of individual business units. Overseeing the financial health of these specific lines, the SVP-Business Line Chief Financial Officer ensures that each unit aligns with the broader corporate goals of growth and stability. This leadership role involves collaborating with business line leaders to optimize resource allocation and improve operational margins. By providing granular financial oversight, Kyle Furry directly impacts the company's ability to make informed strategic decisions. Ultimately, Furry secures the financial performance of the business lines, ensuring that each segment contributes effectively to the overall success and diversified service capabilities of the organization.

Chris Maudlin, the Senior Vice President, Chief Operating Officer at Wintrust, directs internal operational workflows and infrastructure efficiency across the community banking franchise. Maudlin architects scalable processes that allow local banks to maintain autonomy while benefiting from the centralized resources of the larger organization. Overseeing the integration of operational systems, the Senior Vice President, Chief Operating Officer ensures that commercial and personal banking services function with maximum precision. This leadership role involves streamlining back-office procedures to support the diverse needs of businesses and families throughout the Chicagoland area, southern Wisconsin, and northwest Indiana. By optimizing the operational framework, Chris Maudlin directly impacts the company's ability to provide consistent, high-quality service. Ultimately, Maudlin secures the operational foundation required for the organization to scale effectively, ensuring that the community-focused approach remains supported by robust, efficient, and reliable internal systems.

Paul Carlisle, the Chief Operating Officer & Market Head, Commercial Banking at Wintrust, directs the commercial lending strategy and operational execution for the business banking division. Carlisle architects relationship-based lending programs that provide tailored treasury management and credit solutions to local businesses throughout the Chicagoland area. Overseeing the commercial banking market, the Chief Operating Officer & Market Head, Commercial Banking ensures that local decision-making authority remains a primary driver of client satisfaction. This leadership role involves managing the commercial portfolio to support regional economic growth while maintaining strict credit quality standards. By optimizing the commercial banking service model, Paul Carlisle directly impacts the company's ability to serve as a trusted partner to local enterprises. Ultimately, Carlisle secures the market position of the commercial banking division, ensuring that the organization continues to deliver personalized service to businesses of all sizes.

Norah Larke, the Executive Vice President & Chief Human Resources Officer at Wintrust, directs all talent acquisition, organizational development, and employee engagement initiatives. Larke architects comprehensive human capital strategies that support the unique community banking model, ensuring that each local bank maintains its distinct identity while adhering to corporate standards. Overseeing the workforce across the Midwest, the Executive Vice President & Chief Human Resources Officer ensures alignment with the company's commitment to personalized service and community involvement. This leadership role involves fostering a culture of professional growth and operational excellence to attract top-tier banking talent. By optimizing internal training programs and performance management systems, Norah Larke directly impacts the company's ability to deliver superior customer experiences. Ultimately, Larke secures the organizational stability necessary for sustained growth, ensuring that the human resources function remains a strategic partner in the broader success of the financial holding company.

Deb Lefevre, the Executive Vice President & Chief Technology Officer at Wintrust, directs the digital transformation and technological infrastructure of the entire organization. Lefevre architects scalable cloud solutions and secure digital banking platforms that enhance the customer experience while preserving the personal touch of community banking. Overseeing the technology roadmap, the Executive Vice President & Chief Technology Officer ensures that all digital initiatives support the diverse needs of local businesses and families. This leadership role involves integrating innovative financial technology to streamline services and improve operational efficiency across the regional footprint. By modernizing the digital landscape, Deb Lefevre directly impacts the company's ability to compete in a rapidly evolving financial market. Ultimately, Lefevre secures the technological future of the organization, ensuring that the company remains at the forefront of digital banking while maintaining the core values that define the community-focused approach.