WinnCompanies Executive and Leadership Team

October, 2026

Leadership Overview

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

Committed to creating sustainable living environments, WinnCompanies delivers high-impact affordable, middle income, and market-rate housing communities across the nation through innovative development and 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 - 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 the national housing portfolio. Overseeing long-term growth initiatives, the Chief Executive Officer ensures alignment between development goals and community impact objectives. This leadership role involves constant engagement with the Board to refine investment strategies across affordable and market-rate sectors. By prioritizing sustainable expansion, Gilbert Winn directly influences the company's ability to address housing needs in diverse markets. Winn maintains a focus on operational excellence, ensuring that every project meets rigorous quality standards. Through consistent evaluation of market trends, the Chief Executive Officer secures the firm's position as a leader in the housing industry. Ultimately, Winn drives the organizational culture toward innovation and social responsibility, fostering a legacy of excellence in property development and management while expanding the national footprint of the enterprise.
    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, the Chief Financial Officer ensures transparency and compliance across all housing development projects. This leadership role involves structuring debt and equity financing to support the acquisition and construction of affordable and market-rate communities. By optimizing capital structures, Susan Malatesta directly impacts the financial viability of large-scale residential initiatives. Malatesta coordinates with external investors and banking partners to secure funding for regional expansion efforts. Through rigorous risk assessment and budget management, the Chief Financial Officer maintains the stability required for long-term growth. Malatesta provides the necessary financial insights to guide executive decision-making, ensuring that every investment aligns with the broader mission of delivering high-impact housing solutions while maximizing returns for stakeholders and partners.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, directs the internal operational workflows and administrative efficiency of the national housing portfolio. Overseeing cross-departmental integration, the Chief Operating Officer ensures that property management and development teams function in perfect harmony. This leadership role involves streamlining business processes to enhance service delivery across diverse housing communities. By implementing scalable operational frameworks, Terri Benskin directly impacts the daily performance and resident satisfaction levels within the portfolio. Benskin monitors key performance indicators to identify areas for improvement in operational output. Through the coordination of corporate resources, the Chief Operating Officer supports the execution of strategic initiatives across all regional markets. Benskin maintains a focus on process optimization, ensuring that the organization remains agile in a competitive housing landscape. Ultimately, Benskin drives operational excellence, fostering a culture of efficiency that supports the company's mission of providing high-quality living environments.

    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 defense-related residential projects, the Chief Operating Officer, Military Housing Services ensures that facilities meet the highest standards of safety and comfort. This leadership role involves managing complex partnerships with government entities to provide high-quality housing solutions for service members. By focusing on the specific needs of military families, Douglas Jones directly impacts the quality of life for residents in these specialized communities. Jones coordinates with site managers to maintain operational readiness and facility maintenance across the national portfolio. Through strategic oversight of service delivery, the Chief Operating Officer, Military Housing Services ensures that all military housing projects remain compliant with federal regulations. Jones drives excellence in this niche sector, ensuring that the company fulfills its commitment to those serving the nation.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, directs the property management operations for the entire residential portfolio. Overseeing the day-to-day management of affordable, middle income, and market-rate communities, the President - WinnResidential ensures that every property maintains high occupancy and resident satisfaction. This leadership role involves implementing best practices in property maintenance, leasing, and community engagement. By focusing on the resident experience, Patrick Appleby directly impacts the long-term value and reputation of the housing portfolio. Appleby coordinates with regional managers to ensure that operational standards remain consistent across all locations. Through the application of data-driven management techniques, the President - WinnResidential optimizes property performance and financial outcomes. Appleby monitors market conditions to adjust leasing strategies, ensuring that the company remains competitive. Ultimately, Appleby drives the success of the residential division, fostering vibrant communities that align with the core mission of providing quality housing solutions.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, directs the planning, design, and construction of new housing communities. Overseeing the entire development pipeline, the President, WinnDevelopment ensures that projects move from concept to completion while meeting strict quality and budget requirements. This leadership role involves navigating complex zoning, financing, and construction challenges to deliver affordable and market-rate housing. By managing the development lifecycle, Adam Stein directly impacts the growth and expansion of the company's real estate footprint. Stein coordinates with architects, contractors, and local stakeholders to ensure that every development project enhances the surrounding community. Through the implementation of sustainable building practices, the President, WinnDevelopment creates long-lasting value for residents and investors. Stein monitors construction progress to ensure timely delivery of new housing units. Ultimately, Stein drives the development strategy, ensuring that the company continues to innovate and address the critical need for high-quality housing across the nation.

    Explore Leadership Teams in Construction Management

    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.