Total Wine & More Executive and Leadership Team

August, 2026

Leadership Overview

Total Wine & More has 4 executives leading key functions including strategy, financial oversight, technology infrastructure, and human capital management.

Committed to providing an unparalleled selection of beverages, Total Wine & More delivers exceptional value and expertise to customers across the United States through a robust retail network.

Leadership Roles at Total Wine & More

  • Chief Executive Officer - Ryan Ross
  • Chief Financial Officer - Brandon Wilkerson
  • Interim Chief Technology Officer - Casey Craig
  • Chief People Officer - Matthew Lutcavage
  • Ryan Ross - Chief Executive Officer

    Ryan Ross, the Chief Executive Officer at Total Wine & More, directs the overarching corporate strategy and long-term growth initiatives for the national retail organization. By overseeing the expansion of the wine, spirits, and beer product portfolio, the Chief Executive Officer ensures market competitiveness across diverse regional landscapes. Ryan Ross maintains direct accountability for the alignment of operational goals with the broader mission of providing superior customer experiences. This leadership role involves constant collaboration with the Board to refine the retail model and optimize supply chain efficiency. Through the implementation of data-driven decision-making, the Chief Executive Officer drives sustainable revenue growth and strengthens the brand presence in the competitive beverage industry. Ross prioritizes the integration of innovative retail practices to maintain the company's position as a market leader while fostering a culture of excellence throughout the entire organization.

    Brandon Wilkerson - Chief Financial Officer

    Brandon Wilkerson, the Chief Financial Officer at Total Wine & More, manages the fiscal health and capital allocation strategies for the enterprise. Overseeing financial planning, reporting, and risk management, the Chief Financial Officer ensures the stability of the company's extensive retail operations. Brandon Wilkerson directs the budgeting processes that support the procurement of wine, spirits, and beer products, balancing inventory investment with profitability targets. This role requires close coordination with executive leadership to evaluate the financial viability of new market entries and infrastructure upgrades. By monitoring economic trends and operational costs, the Chief Financial Officer secures the resources necessary for long-term expansion. Wilkerson maintains rigorous oversight of financial controls, ensuring transparency and compliance across all business units. Through disciplined fiscal management, the Chief Financial Officer supports the company's ability to deliver consistent value to customers and stakeholders alike.

    Casey Craig - Interim Chief Technology Officer

    Casey Craig, the Interim Chief Technology Officer at Total Wine & More, architects the digital infrastructure and technological roadmap supporting the company's retail ecosystem. Overseeing the integration of e-commerce platforms and point-of-sale systems, the Interim Chief Technology Officer ensures seamless transaction processing for wine, spirits, and beer sales. Casey Craig directs the cybersecurity initiatives and data analytics teams to protect customer information while providing actionable insights into consumer purchasing behavior. This leadership role involves modernizing legacy systems to improve operational efficiency and enhance the omnichannel shopping experience. By aligning technical capabilities with business objectives, the Interim Chief Technology Officer drives digital transformation across the national footprint. Craig manages the deployment of scalable software solutions that support inventory management and supply chain visibility. Through strategic technology investments, the Interim Chief Technology Officer enables the company to adapt rapidly to evolving retail demands and digital market trends.

    Matthew Lutcavage - Chief People Officer

    Matthew Lutcavage, the Chief People Officer at Total Wine & More, designs the human capital strategy and organizational development programs for the entire workforce. Overseeing talent acquisition, employee engagement, and leadership training, the Chief People Officer ensures the company attracts and retains top-tier professionals across all retail locations. Matthew Lutcavage directs the implementation of performance management systems that align individual contributions with the corporate mission of providing expert service in the beverage industry. This role involves fostering an inclusive workplace culture that supports professional growth and operational excellence. By managing compensation structures and benefits programs, the Chief People Officer maintains high levels of employee satisfaction and productivity. Lutcavage collaborates with other executives to address workforce planning needs and organizational design challenges. Through proactive human resources management, the Chief People Officer strengthens the company's ability to deliver high-quality service to customers in every market.

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    Frequently Asked Questions Regarding Total Wine & More Top Executives and Leadership Team

    Who leads Total Wine & More?
    Total Wine & More is led by Ryan Ross (Chief Executive Officer), along with executives such as Brandon Wilkerson (Chief Financial Officer) and Casey Craig (Interim Chief Technology Officer).
    Who is part of Total Wine & More’s executive team?
    The executive team of Total Wine & More includes leaders such as Ryan Ross (Chief Executive Officer), Brandon Wilkerson (Chief Financial Officer), Casey Craig (Interim Chief Technology Officer) and other senior executives.
    How many executives does Total Wine & More have?
    Total Wine & More has 4 executives leading key business areas.
    What roles are included in Total Wine & More’s leadership team?
    The leadership team of Total Wine & More includes roles such as Chief Executive Officer, Chief Financial Officer, Interim Chief Technology Officer, Chief People Officer.