Senior Director of Retail

Senior Director of Retail

$110,000-140,000 with bonus eligibility

Goodwill Industries of the Chesapeake is seeking a Senior Director of Retail to provide enterprise-level leadership for a multi-site retail operation that directly funds mission programs across our communities.

This role sets the strategic direction for store performance, merchandising, production, customer experience, and retail talent development-positioning retail as a key driver of organizational growth, financial sustainability, and mission impact.

Retail is a core engine of Goodwill's mission. The Senior Director of Retail leads strategy, execution, and cross-functional alignment across a complex retail footprint, ensuring stores operate efficiently, perform strongly, and deliver an exceptional customer experience-while advancing workforce development and community outcomes.

This role blends strategic vision with operational leadership, partnering closely with executive leadership and departments including eCommerce, Finance, Operations & Sustainability, and Real Estate.

• Lead the overall strategy, performance, and alignment of all retail operations across multiple locations
• Drive 8-12% year-over-year sales growth using data, market insights, and operational innovation
• Position retail as a catalyst for mission impact and long-term organizational growth

• Develop and manage multi-million-dollar operating budgets, maintaining results within 5% of budget
• Ensure 100% achievement of production targets while maintaining 50%+ textile sell-through rates
• Increase average transaction value by 5% through merchandising and pricing strategies
• Lead company-wide initiatives that increase customer engagement, including sustaining 40%+ round-up participation

• Oversee store performance and rapidly address underperformance, achieving 10%+ improvements within 90 days when needed
• Ensure consistent execution of merchandising standards, seasonal plans, and promotional campaigns
• Represent retail operations in executive, board-level, and cross-functional leadership forums

• Build and lead a high-performing retail leadership culture grounded in accountability and continuous improvement
• Strengthen leadership pipelines through coaching, training, and succession planning
• Partner with HR to maintain store-level vacancy rates below 15%

• Ensure a consistent, high-quality customer experience across all locations
• Reduce customer complaints through proactive training, leadership standards, and responsive resolution
• Protect and advance brand standards across merchandising, store environments, and customer engagement

• Ensure 100% compliance with safety, loss prevention, and organizational policies
• Lead annual reviews of audits, procedures, and risk controls in partnership with HR and Loss Prevention

• Partner closely with Finance, eCommerce, Operations & Sustainability, Real Estate, and other departments
• Lead cross-functional initiatives that drive alignment, transparency, and shared accountability

• High school diploma or GED (required)
• 8-10 years of progressive retail leadership experience, including multi-unit oversight
• Demonstrated success leading large, complex, multi-site retail operations
• Strong executive-level decision-making and people leadership experience

• Bachelor's degree in business, retail management, or a related field
• Experience scaling operations, improving underperforming locations, and leading enterprise initiatives

• Strategic, visionary leadership with strong execution capability
• Advanced financial and operational acumen
• Executive presence and ability to influence at all organizational levels
• Strong cross-functional collaborator and relationship builder
• Data-driven decision-maker with a bias toward action
• Commitment to diversity, equity, inclusion, and community impact

• Combination of office and retail environments
• Regular travel throughout Goodwill's service territory (Maryland and Eastern Shore)
• Access to a personal vehicle required

Goodwill Industries of the Chesapeake offers competitive compensation, executive-level impact, and the opportunity to lead a mission-driven retail enterprise that directly funds community programs and workforce opportunities.

?? Learn more about our mission, benefits, and impact:
https://goodwillches.org/about-us/goodwill-careers/