WinnCompanies Executive and Leadership Team

June, 2026

Leadership Overview

WinnCompanies has 6 executives leading key functions including strategy, finance, operations, military housing, development, and residential management.

Driven by a commitment to community, WinnCompanies develops and manages diverse housing communities nationwide, focusing on impactful affordable, middle-income, and market-rate residences.

Leadership Roles at WinnCompanies

  • Chief Executive Officer - Gilbert Winn
  • Chief Financial Officer - Susan Malatesta
  • Chief Operating Officer - Terri Benskin
  • Chief Operating Officer, Military Housing Services - Douglas Jones
  • President, WinnDevelopment - Adam Stein
  • President - WinnResidential - Patrick Appleby
  • Gilbert Winn - Chief Executive Officer

    Gilbert Winn, the Chief Executive Officer at WinnCompanies, directs the overarching strategic vision and corporate direction for the national developer and manager of housing communities. Overseeing all business units, Gilbert Winn ensures alignment with the company's founding mission of creating high-impact affordable, middle-income, and market-rate housing. This leadership role involves driving innovation in development and management practices across the United States. By fostering strong relationships with stakeholders and guiding long-term growth initiatives, Gilbert Winn solidifies the company's market position. The Chief Executive Officer's focus remains on expanding the portfolio while upholding the highest standards of quality and community development. This executive's strategic oversight is critical to the sustained success and expansion of WinnCompanies' national footprint.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, manages all financial operations and fiscal strategy for the organization. Overseeing budgeting, forecasting, and financial reporting, Susan Malatesta ensures the fiscal health and stability of the company's diverse housing development and management activities. This critical role involves securing capital for new projects and managing existing financial structures to support WinnCompanies' mission of creating affordable and market-rate housing. By optimizing financial performance and mitigating risk, the Chief Financial Officer directly contributes to the company's ability to expand its national reach. Susan Malatesta's expertise guides investment decisions and ensures compliance with all financial regulations across the United States. The Chief Financial Officer's leadership is integral to sustaining the company's growth and operational capacity.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, directs the operational execution of the company's housing development and management strategies nationwide. Overseeing day-to-day operations across all property types, Terri Benskin ensures efficient and effective service delivery for affordable, middle-income, and market-rate communities. This leadership position involves optimizing property management processes and driving operational excellence throughout the organization. By implementing best practices and enhancing operational workflows, the Chief Operating Officer supports the company's commitment to quality housing. Terri Benskin's focus is on streamlining operations to maximize resident satisfaction and financial performance. The Chief Operating Officer's role is fundamental to the successful management and expansion of WinnCompanies' extensive portfolio.

    Douglas Jones - Chief Operating Officer, Military Housing Services

    Douglas Jones, the Chief Operating Officer, Military Housing Services at WinnCompanies, leads the specialized operations dedicated to military housing communities. Overseeing the management and development of these critical residences, Douglas Jones ensures high standards of service and quality for military families across the United States. This executive role involves managing all aspects of military housing operations, from property maintenance to resident relations, aligning with the specific needs of military personnel and their families. By driving operational efficiency and strategic planning within this sector, the Chief Operating Officer, Military Housing Services enhances the living experience for residents. Douglas Jones's leadership is vital for maintaining and expanding WinnCompanies' commitment to serving the military community. The Chief Operating Officer, Military Housing Services ensures the successful delivery of housing solutions for those serving the nation.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, spearheads the company's development initiatives across the nation. Overseeing all aspects of new project acquisition, planning, and execution, Adam Stein drives the creation of impactful affordable, middle-income, and market-rate housing communities. This leadership position involves identifying strategic development opportunities and managing the complex process of bringing new properties to fruition. By fostering innovation in design and construction, the President, WinnDevelopment ensures that new projects meet the highest standards of quality and community integration. Adam Stein's focus is on expanding the development pipeline and delivering value through thoughtful urban planning and real estate investment. The President, WinnDevelopment's strategic vision is crucial for the company's continued growth and portfolio diversification.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, directs the comprehensive management of the company's residential property portfolio nationwide. Overseeing a vast array of affordable, middle-income, and market-rate housing communities, Patrick Appleby ensures exceptional property management services and resident satisfaction. This executive role involves leading teams responsible for leasing, maintenance, resident engagement, and operational efficiency across all managed properties. By implementing strategic management practices and fostering a culture of service excellence, the President - WinnResidential enhances the value and appeal of the company's housing assets. Patrick Appleby's leadership is key to maintaining WinnCompanies' reputation for quality residential management. The President - WinnResidential drives operational success and resident well-being across the extensive WinnResidential portfolio.

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    Frequently Asked Questions Regarding WinnCompanies Top Executives and Leadership Team

    Who leads WinnCompanies?
    WinnCompanies is led by Gilbert Winn (Chief Executive Officer), along with executives such as Susan Malatesta (Chief Financial Officer) and Terri Benskin (Chief Operating Officer).
    Who is part of WinnCompanies’s executive team?
    The executive team of WinnCompanies includes leaders such as Gilbert Winn (Chief Executive Officer), Susan Malatesta (Chief Financial Officer), Terri Benskin (Chief Operating Officer) and other senior executives.
    How many executives does WinnCompanies have?
    WinnCompanies has 6 executives leading key business areas.
    What roles are included in WinnCompanies’s leadership team?
    The leadership team of WinnCompanies includes roles such as Chief Executive Officer, Chief Financial Officer, Chief Operating Officer, Chief Operating Officer, Military Housing Services, President, WinnDevelopment.