WinnCompanies Executive and Leadership Team

October, 2026

Leadership Overview

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

Committed to creating sustainable living environments, WinnCompanies delivers high-impact affordable, middle-income, and market-rate housing solutions across the United States to foster vibrant, inclusive communities.

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 - WinnResidential - Patrick Appleby
  • President, WinnDevelopment - Adam Stein
  • Gilbert Winn - Chief Executive Officer

    Gilbert Winn, the Chief Executive Officer at WinnCompanies, directs the overarching strategic vision for this national developer and manager of housing communities. Overseeing the long-term growth trajectory, the Chief Executive Officer ensures alignment between corporate objectives and the evolving needs of affordable and market-rate housing sectors. This leadership role involves constant engagement with the Board to refine investment strategies and expand the national footprint. By prioritizing sustainable development practices, Gilbert Winn directly impacts the company's ability to provide high-quality living spaces across diverse markets. Ultimately, the Chief Executive Officer secures the financial and operational health of the organization, driving innovation in housing policy and community impact while maintaining the core mission established in 1971. Through rigorous oversight of executive initiatives, the Chief Executive Officer maintains the firm's reputation as a leader in the residential development industry.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, directs the fiscal strategy and capital allocation for the organization's diverse housing portfolio. Overseeing financial reporting and risk management, the Chief Financial Officer ensures the stability of investments in affordable and market-rate developments. This leadership role involves coordinating with institutional partners and lenders to secure funding for new projects and ongoing operations. By maintaining rigorous financial controls, Susan Malatesta directly impacts the company's capacity for sustained growth and long-term viability. Ultimately, the Chief Financial Officer provides the economic foundation necessary for the firm to execute its mission of creating high-impact housing communities. Through precise management of the balance sheet and capital structure, the Chief Financial Officer supports the strategic objectives of the executive team, ensuring that every development project aligns with the firm's financial performance targets and broader market impact goals.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, manages the daily operational efficiency of the firm's extensive portfolio of housing communities. Overseeing internal processes, the Chief Operating Officer ensures that property management standards remain high across all affordable, middle-income, and market-rate assets. This leadership role involves streamlining workflows between regional teams to optimize service delivery and resident satisfaction. By implementing scalable operational frameworks, Terri Benskin directly impacts the company's ability to maintain high occupancy rates and operational excellence. Ultimately, the Chief Operating Officer drives performance improvements that support the broader organizational goals of providing stable housing. Through constant monitoring of operational metrics, the Chief Operating Officer identifies opportunities for cost reduction and service enhancement, ensuring that the company remains a top-tier manager of residential properties while navigating the complexities of the national housing market.

    Douglas Jones - Chief Operating Officer, Military Housing Services

    Douglas Jones, the Chief Operating Officer, Military Housing Services at WinnCompanies, directs the specialized operations required to manage housing for military personnel and families. Overseeing the unique requirements of these communities, the Chief Operating Officer, Military Housing Services ensures that service delivery meets the high standards expected by government partners and residents. This leadership role involves managing complex logistics and maintenance programs across various military installations. By focusing on the specific needs of this demographic, Douglas Jones directly impacts the quality of life for service members and their families. Ultimately, the Chief Operating Officer, Military Housing Services drives operational excellence within this niche sector, ensuring that all housing assets remain safe, modern, and well-maintained. Through strategic coordination with military stakeholders, the Chief Operating Officer, Military Housing Services maintains the firm's commitment to providing superior housing solutions in the specialized military housing market.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, directs the management and leasing operations for the firm's vast residential portfolio. Overseeing property performance, the President - WinnResidential ensures that all affordable, middle-income, and market-rate communities operate at peak efficiency. This leadership role involves leading regional teams to enhance resident experiences and maintain property value through proactive maintenance and community engagement. By optimizing leasing strategies and operational workflows, Patrick Appleby directly impacts the company's revenue growth and market presence. Ultimately, the President - WinnResidential drives the success of the residential management division, ensuring that every community serves as a model for high-quality housing. Through constant focus on operational standards and resident satisfaction, the President - WinnResidential maintains the firm's reputation for excellence in property management, ensuring that all residential assets contribute positively to the company's overall mission and market impact.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, directs the planning, design, and construction of new housing communities. Overseeing the development pipeline, the President, WinnDevelopment ensures that every project aligns with the firm's mission to provide affordable and market-rate housing. This leadership role involves navigating complex regulatory environments and collaborating with local stakeholders to bring new developments to fruition. By managing the entire lifecycle of construction projects, Adam Stein directly impacts the company's ability to expand its footprint and address housing shortages. Ultimately, the President, WinnDevelopment drives the creation of sustainable and impactful living spaces that serve diverse populations. Through strategic site acquisition and project execution, the President, WinnDevelopment ensures that the firm remains at the forefront of residential development, delivering high-quality communities that meet the evolving needs of residents while achieving the company's long-term growth objectives.

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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 - WinnResidential.