WinnCompanies Executive and Leadership Team

May, 2026

Leadership Overview

WinnCompanies has 5 executives leading key functions including strategy, finance, operations, property management, and development.

Driven by a commitment to community, WinnCompanies develops and manages diverse housing communities nationwide, focusing on impactful affordable, middle-income, and market-rate properties.

Leadership Roles at WinnCompanies

  • Chief Executive Officer - Gilbert Winn
  • Chief Financial Officer - Susan Malatesta
  • Chief Operating Officer - Terri Benskin
  • 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. Winn guides the company's national expansion and operational framework, ensuring alignment with its mission to develop and manage high-impact housing communities. This leadership role involves setting financial targets, fostering key stakeholder relationships, and driving innovation across all business units. Overseeing the executive team, Gilbert Winn ensures that strategic initiatives translate into tangible results, reinforcing WinnCompanies' position as a leader in affordable, middle-income, and market-rate housing development and management. The Chief Executive Officer's focus remains on sustainable growth and enhancing community value through responsible development practices.
    Gilbert Winn

    Susan Malatesta - Chief Financial Officer

    Susan Malatesta, the Chief Financial Officer at WinnCompanies, manages all financial operations and fiscal strategy. Malatesta oversees budgeting, forecasting, and financial reporting, ensuring the fiscal health and stability of the organization. This critical role involves securing capital for development projects, managing investment portfolios, and optimizing financial performance across WinnCompanies' diverse portfolio of housing communities. Directing the finance department, Susan Malatesta ensures compliance with all regulatory requirements and implements robust financial controls. The Chief Financial Officer's expertise is vital in supporting the company's mission to deliver impactful affordable, middle-income, and market-rate housing, driving long-term value for residents and stakeholders.

    Terri Benskin - Chief Operating Officer

    Terri Benskin, the Chief Operating Officer at WinnCompanies, directs the day-to-day operational execution across all housing communities. Benskin oversees property management, asset preservation, and resident services, ensuring high standards of quality and efficiency. This leadership position involves optimizing operational workflows, implementing best practices in property management, and driving operational excellence throughout the organization. Leading the operations division, Terri Benskin ensures seamless integration between development and management functions, supporting the company's commitment to impactful housing solutions. The Chief Operating Officer's strategic focus is on enhancing resident satisfaction and maximizing asset performance for affordable, middle-income, and market-rate properties nationwide.

    Patrick Appleby - President - WinnResidential

    Patrick Appleby, the President - WinnResidential at WinnCompanies, leads the property management division, WinnResidential. Appleby directs the strategic growth and operational performance of the company's extensive portfolio of managed housing communities. This executive role involves overseeing all aspects of property operations, including leasing, resident relations, maintenance, and financial performance for affordable, middle-income, and market-rate properties. Driving the WinnResidential business unit, Patrick Appleby ensures the delivery of exceptional resident experiences and maximizes property value. The President - WinnResidential's leadership is focused on maintaining high occupancy rates, implementing innovative management strategies, and upholding WinnCompanies' reputation for excellence in housing management.

    Adam Stein - President, WinnDevelopment

    Adam Stein, the President, WinnDevelopment at WinnCompanies, spearheads the company's development arm, WinnDevelopment. Stein directs the acquisition, planning, and construction of new housing projects, focusing on impactful affordable, middle-income, and market-rate communities. This senior leadership position involves identifying strategic development opportunities, securing financing, and managing the entire development lifecycle from concept to completion. Leading the WinnDevelopment team, Adam Stein ensures projects align with community needs and company objectives, driving growth and expanding WinnCompanies' national footprint. The President, WinnDevelopment's vision is crucial for creating sustainable, high-quality housing solutions that benefit residents and 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 5 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, President - WinnResidential, President, WinnDevelopment.