WinnCompanies Executive and Leadership Team

July, 2026

Leadership Overview

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

Driven by a commitment to community, WinnCompanies develops and manages housing across the nation, focusing on affordable, middle-income, and market-rate 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 corporate strategy and vision for the national developer and manager of housing communities. Overseeing all business units, Gilbert Winn ensures alignment with the company's founding mission to create high-impact affordable, middle-income, and market-rate housing. This leadership role involves guiding expansion efforts across the United States, fostering innovation in property development and management, and maintaining strong relationships with stakeholders. The Chief Executive Officer's focus remains on driving sustainable growth and upholding the company's reputation for quality and integrity in every community served. Strategic decisions under Gilbert Winn's purview impact operational efficiency and long-term financial health, solidifying WinnCompanies' position in the housing sector.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, manages all financial operations and strategic financial planning for the organization. Overseeing budgeting, forecasting, and capital allocation, Susan Malatesta ensures the fiscal health and stability of the company's diverse portfolio of housing communities. This critical role involves managing investor relations, securing financing for development projects, and optimizing financial performance across WinnResidential and WinnDevelopment. The Chief Financial Officer's expertise is vital in navigating complex market conditions and driving profitability while supporting the company's commitment to affordable and market-rate housing. By implementing robust financial controls and identifying growth opportunities, Susan Malatesta directly contributes to the long-term sustainability and expansion of WinnCompanies' national presence.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, directs the operational execution across the company's extensive housing portfolio. Overseeing day-to-day management and service delivery for WinnResidential, Terri Benskin ensures consistent quality and resident satisfaction in affordable, middle-income, and market-rate communities nationwide. This leadership position involves optimizing operational workflows, implementing best practices in property management, and driving efficiency across all managed properties. The Chief Operating Officer's focus is on enhancing operational performance, managing resources effectively, and supporting the strategic goals of WinnCompanies. By leading operational teams and fostering a culture of excellence, Terri Benskin plays a key part in maintaining the company's reputation for reliable and high-quality housing solutions across the United States.

    Douglas Jones - Chief Operating Officer, Military Housing Services

    Douglas Jones, the Chief Operating Officer, Military Housing Services at WinnCompanies, spearheads the specialized operations for military housing communities. Overseeing the development, management, and resident services for these unique properties, Douglas Jones ensures high standards of living and operational excellence for military families across the nation. This role demands a deep understanding of military housing regulations, partnership management with government entities, and the delivery of comprehensive support services. The Chief Operating Officer, Military Housing Services' primary objective is to enhance the quality of life for residents through efficient property management and community development. By driving strategic initiatives within this specialized sector, Douglas Jones strengthens WinnCompanies' commitment to serving the military community with dedicated and effective housing solutions.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, leads the property management division responsible for a vast portfolio of housing communities. Overseeing operations for affordable, middle-income, and market-rate properties nationwide, Patrick Appleby drives service excellence and resident satisfaction. This executive role involves managing regional teams, implementing innovative property management strategies, and ensuring operational efficiency across all WinnResidential assets. The President - WinnResidential's focus is on maximizing property performance, fostering strong client relationships, and upholding the company's commitment to quality housing. By directing the strategic growth and operational standards of WinnResidential, Patrick Appleby significantly contributes to the company's overall success and market leadership in property management.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, directs the company's real estate development arm, focusing on creating new housing communities. Overseeing all aspects of the development lifecycle, from site acquisition and financing to design and construction, Adam Stein drives the creation of affordable, middle-income, and market-rate housing projects across the United States. This leadership position involves strategic planning, market analysis, and fostering partnerships to bring complex development projects to fruition. The President, WinnDevelopment's objective is to expand WinnCompanies' footprint through innovative and impactful development initiatives. By leading the WinnDevelopment team, Adam Stein ensures the successful execution of projects that meet community needs and contribute to the company's growth and mission.

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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.