WinnCompanies Executive and Leadership Team

August, 2026

Leadership Overview

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

Focused on creating sustainable living environments, WinnCompanies delivers high-impact affordable, middle income, and market-rate housing communities across the nation through expert development and management.

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 corporate strategy and long-term vision for the organization. Overseeing the national portfolio of affordable and market-rate housing, the Chief Executive Officer ensures alignment between development goals and operational excellence. This leadership role involves constant engagement with the Board to maintain financial health and market competitiveness. By fostering innovation in community design and management, Gilbert Winn drives the expansion of housing solutions across diverse regional markets. The Chief Executive Officer prioritizes sustainable growth while maintaining the core mission of providing high-quality living spaces. Through rigorous oversight of all business units, Winn maintains the company's reputation as a leader in the housing sector. Strategic decisions made by the Chief Executive Officer directly influence the company's ability to address complex housing needs in various communities, ensuring consistent value delivery for stakeholders and residents alike.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, architects the financial framework and capital strategies necessary for large-scale housing development. Overseeing fiscal planning, the Chief Financial Officer ensures the company maintains a robust balance sheet while pursuing new investment opportunities. This leadership role involves managing complex funding structures, including tax credits and private equity, to support affordable and market-rate projects. By optimizing capital allocation, Susan Malatesta drives long-term financial sustainability and growth. The Chief Financial Officer monitors economic trends to mitigate risks and capitalize on market shifts across the national landscape. Through precise financial reporting and analysis, Malatesta provides the executive team with actionable insights for strategic decision-making. The Chief Financial Officer maintains strong relationships with institutional investors and lenders to secure the necessary resources for ongoing operations. Financial discipline enforced by the Chief Financial Officer remains central to the company's ability to deliver high-impact housing solutions.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, manages the daily operational workflows and internal processes that support the firm's extensive housing portfolio. Overseeing the integration of property management systems, the Chief Operating Officer ensures efficiency across all residential assets. This leadership role involves coordinating with regional teams to optimize performance metrics and resident satisfaction levels. By streamlining administrative functions, Terri Benskin drives operational scalability and cost-effectiveness throughout the organization. The Chief Operating Officer monitors key performance indicators to identify opportunities for process improvement and resource allocation. Through active collaboration with department heads, Benskin maintains high standards of service delivery across the national footprint. The Chief Operating Officer focuses on operational resilience, ensuring that all housing communities meet rigorous quality benchmarks. Strategic initiatives led by the Chief Operating Officer directly support the company's objective of maintaining excellence in property management and operational stability.

    Douglas Jones - Chief Operating Officer, Military Housing Services

    Douglas Jones, the Chief Operating Officer, Military Housing Services at WinnCompanies, directs the specialized operations and management of housing communities serving military personnel. Overseeing the unique requirements of these installations, the Chief Operating Officer, Military Housing Services ensures compliance with federal standards and high-quality living conditions. This leadership role involves managing large-scale infrastructure projects and resident services tailored to the needs of military families. By optimizing service delivery, Douglas Jones drives operational excellence within this critical sector. The Chief Operating Officer, Military Housing Services coordinates with government partners to align project outcomes with national defense housing objectives. Through proactive maintenance and community engagement, Jones maintains the integrity and value of these specialized assets. The Chief Operating Officer, Military Housing Services focuses on operational efficiency to ensure that military housing remains a top-tier option for service members. Strategic oversight provided by the Chief Operating Officer, Military Housing Services directly impacts the quality of life for military families.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, architects the development pipeline and project execution strategies for new housing communities. Overseeing the entire lifecycle of development projects, the President, WinnDevelopment ensures that new construction and rehabilitation efforts meet the company's high standards for quality and affordability. This leadership role involves navigating complex zoning, financing, and community relations to bring projects to fruition. By identifying strategic land acquisition opportunities, Adam Stein drives the expansion of the company's footprint in key markets. The President, WinnDevelopment coordinates with architects, contractors, and local officials to ensure timely project delivery. Through innovative design and sustainable building practices, Stein maintains the company's competitive edge in the development sector. The President, WinnDevelopment focuses on creating vibrant, mixed-income communities that address critical housing shortages. Strategic leadership from the President, WinnDevelopment directly contributes to the company's mission of providing high-impact housing solutions across the nation.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, directs the management and leasing operations for the firm's extensive residential portfolio. Overseeing the day-to-day performance of diverse housing communities, the President - WinnResidential ensures that resident needs are met while maintaining high occupancy rates. This leadership role involves implementing best practices in property management, marketing, and customer service to enhance asset value. By fostering a culture of excellence among property staff, Patrick Appleby drives operational success across the national portfolio. The President - WinnResidential monitors market trends to adjust leasing strategies and maintain competitive positioning. Through effective communication with regional managers, Appleby ensures consistent service delivery and operational compliance. The President - WinnResidential focuses on resident retention and community building to create stable, thriving living environments. Strategic initiatives led by the President - WinnResidential directly support the company's goal of providing high-quality, well-managed housing for a wide range of residents.

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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.