WinnCompanies Executive and Leadership Team

July, 2026

Leadership Overview

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

Driven by a commitment to creating and managing exceptional housing communities, WinnCompanies focuses on delivering high-quality affordable, middle-income, and market-rate housing nationwide, impacting urban and suburban landscapes.

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 major business units, Gilbert Winn ensures alignment with the company's founding mission of providing high-impact housing solutions across affordable, middle-income, and market-rate sectors. This leadership role involves guiding expansion initiatives and fostering innovation in property development and management. By setting ambitious goals and championing a culture of excellence, Gilbert Winn drives the company's sustained growth and market leadership. The Chief Executive Officer's purview extends to financial oversight, operational efficiency, and maintaining strong relationships with stakeholders, investors, and community partners, solidifying WinnCompanies' reputation for quality and integrity in the real estate sector.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, manages the company's financial health and strategic fiscal planning. Overseeing all financial operations, including accounting, budgeting, and investment analysis, Susan Malatesta ensures robust financial stewardship for the national housing developer and manager. This position is vital for maintaining the company's financial stability and supporting its ambitious growth objectives across affordable, middle-income, and market-rate housing projects. By providing critical financial insights and managing capital allocation, the Chief Financial Officer enables WinnCompanies to undertake significant development and acquisition opportunities. Susan Malatesta's expertise guides financial strategies that support long-term value creation and operational sustainability for the company's extensive portfolio.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, executes the day-to-day operational strategies across the company's diverse portfolio of housing communities. Overseeing property management and development operations, Terri Benskin ensures seamless execution of services that uphold WinnCompanies' commitment to quality and resident satisfaction. This critical role involves optimizing operational workflows, implementing best practices in property management, and driving efficiency across all residential and development projects nationwide. By focusing on operational excellence, the Chief Operating Officer enhances the value and performance of the company's assets. Terri Benskin's leadership ensures that the company's national footprint, encompassing affordable, middle-income, and market-rate housing, operates cohesively and effectively, meeting the needs of residents and stakeholders.

    Douglas Jones - Chief Operating Officer, Military Housing Services

    Douglas Jones, the Chief Operating Officer, Military Housing Services at WinnCompanies, directs the specialized operations for military housing communities. Overseeing the management and development of properties serving military families nationwide, Douglas Jones ensures high standards of service and quality of life. This role is crucial for fulfilling WinnCompanies' commitment to providing exceptional housing solutions for service members and their families. By focusing on the unique needs of military communities, the Chief Operating Officer, Military Housing Services drives operational efficiency and resident satisfaction within this specific sector. Douglas Jones's leadership ensures that military housing projects meet stringent requirements and contribute positively to the well-being of residents and the readiness of military installations.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, leads the strategic direction and execution of new housing development projects. Overseeing all aspects of the development pipeline, Adam Stein drives the creation of innovative and impactful affordable, middle-income, and market-rate housing communities across the nation. This leadership position involves identifying new opportunities, managing project lifecycles from conception to completion, and ensuring developments align with WinnCompanies' mission and financial objectives. By fostering strong relationships with partners and stakeholders, the President, WinnDevelopment facilitates the successful launch of complex real estate ventures. Adam Stein's focus on strategic growth and quality development strengthens WinnCompanies' position as a national leader in housing.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, spearheads the management and operational success of the company's residential property portfolio. Overseeing a vast network of housing communities, Patrick Appleby ensures exceptional service delivery and resident satisfaction across affordable, middle-income, and market-rate segments nationwide. This role is pivotal in optimizing property performance, implementing innovative management strategies, and driving operational efficiencies. By focusing on resident experience and asset value enhancement, the President - WinnResidential contributes significantly to WinnCompanies' market reputation. Patrick Appleby's leadership ensures the effective and sustainable management of properties, reinforcing the company's commitment to creating thriving communities.

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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.