WinnCompanies Executive and Leadership Team

September, 2026

Leadership Overview

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

Committed to creating sustainable living environments, WinnCompanies advances the national landscape of affordable, middle-income, and market-rate housing through innovative development and professional management practices.

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 this national housing developer. By overseeing the expansion of affordable and market-rate housing portfolios, the Chief Executive Officer ensures alignment with the core mission of creating high-impact residential communities. Gilbert Winn manages relationships with key stakeholders and the Board to maintain financial health and operational excellence across all regions. This leadership role involves identifying new market opportunities and fostering partnerships that support sustainable growth. Through rigorous oversight of development pipelines, the Chief Executive Officer drives the company toward achieving ambitious housing goals. By prioritizing community impact and operational efficiency, Winn maintains a competitive edge in the national real estate sector. The Chief Executive Officer consistently evaluates market trends to refine the strategic direction of the organization, ensuring that every project contributes to the broader objective of providing quality housing solutions.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, manages the fiscal health and capital allocation strategies for the entire organization. Overseeing complex financial reporting and budgeting processes, the Chief Financial Officer ensures that all development projects remain economically viable and aligned with corporate objectives. Susan Malatesta directs the treasury functions and risk management protocols necessary for navigating the national housing market. This leadership role involves coordinating with the Board to secure funding for large-scale residential initiatives and optimizing the capital structure to support long-term growth. By implementing robust financial controls, the Chief Financial Officer safeguards the assets of the company while facilitating investment in new communities. Malatesta monitors economic indicators to mitigate potential risks, ensuring that the financial foundation remains stable during periods of expansion. Through precise fiscal planning and strategic resource management, the Chief Financial Officer enables the successful execution of diverse housing projects across the country.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, directs the daily operational activities and internal processes that sustain the national housing portfolio. Overseeing the integration of property management systems and service delivery standards, the Chief Operating Officer ensures that every community operates at peak efficiency. Terri Benskin manages cross-functional teams to streamline workflows and improve resident satisfaction across diverse housing types. This leadership role involves implementing operational policies that enhance the quality of life for residents while maintaining strict adherence to regulatory requirements. By optimizing internal resources, the Chief Operating Officer drives performance improvements and supports the broader mission of the organization. Benskin coordinates with other C-suite leaders to align operational output with strategic growth targets. Through the continuous refinement of management practices, the Chief Operating Officer maintains high standards of excellence, ensuring that the company remains a leader in the development and management of affordable and market-rate housing communities.

    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 dedicated to military personnel. Overseeing the unique requirements of these residential assets, the Chief Operating Officer, Military Housing Services ensures that all facilities meet the high standards expected by government partners and service members. Douglas Jones manages the logistics of large-scale housing maintenance and resident services across various regional installations. This leadership role involves navigating complex regulatory environments and maintaining strong relationships with military stakeholders to ensure project success. By focusing on the specific needs of military families, the Chief Operating Officer, Military Housing Services drives the delivery of high-quality, reliable housing solutions. Jones coordinates with internal teams to optimize service delivery and operational performance within this niche sector. Through dedicated oversight, the Chief Operating Officer, Military Housing Services secures the long-term viability and reputation of these critical residential communities.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, directs the end-to-end development lifecycle for new housing projects across the nation. Overseeing site acquisition, design, and construction management, the President, WinnDevelopment ensures that every new community aligns with the company's commitment to high-impact, affordable, and market-rate housing. Adam Stein manages the development pipeline and coordinates with local authorities to secure necessary approvals and financing. This leadership role involves leading multidisciplinary teams of architects, engineers, and project managers to bring complex residential visions to life. By focusing on sustainable building practices and innovative design, the President, WinnDevelopment drives the creation of communities that provide lasting value. Stein collaborates with the executive team to identify strategic growth areas and expand the national footprint of the organization. Through meticulous planning and execution, the President, WinnDevelopment transforms raw land and existing structures into vibrant, functional housing environments that serve diverse populations.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, directs the management and leasing operations for the extensive portfolio of residential communities. Overseeing the performance of property management teams, the President - WinnResidential ensures that every community maintains high occupancy rates and superior service standards. Patrick Appleby manages the implementation of marketing strategies and resident engagement programs designed to foster thriving living environments. This leadership role involves optimizing operational costs and enhancing the value of the residential assets through proactive maintenance and capital improvements. By focusing on the resident experience, the President - WinnResidential drives the success of the company's management division. Appleby coordinates with regional managers to ensure consistent application of corporate policies and service excellence across the national footprint. Through strategic oversight of the residential portfolio, the President - WinnResidential maintains the company's reputation as a premier manager of affordable, middle-income, and market-rate housing 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.