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.
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Lead the overall strategy, performance, and alignment of all retail operations across multiple locations
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Drive 8–12% year‑over‑year sales growth using data, market insights, and operational innovation
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Position retail as a catalyst for mission impact and long‑term organizational growth
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Develop and manage multi‑million‑dollar operating budgets, maintaining results within ±5% of budget
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Ensure 100% achievement of production targets while maintaining 50%+ textile sell‑through rates
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Increase average transaction value by 5% through merchandising and pricing strategies
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Lead company‑wide initiatives that increase customer engagement, including sustaining 40%+ round‑up participation
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Oversee store performance and rapidly address underperformance, achieving 10%+ improvements within 90 days when needed
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Ensure consistent execution of merchandising standards, seasonal plans, and promotional campaigns
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Represent retail operations in executive, board‑level, and cross‑functional leadership forums
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Build and lead a high‑performing retail leadership culture grounded in accountability and continuous improvement
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Strengthen leadership pipelines through coaching, training, and succession planning
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Partner with HR to maintain store‑level vacancy rates below 15%
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Ensure a consistent, high‑quality customer experience across all locations
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Reduce customer complaints through proactive training, leadership standards, and responsive resolution
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Protect and advance brand standards across merchandising, store environments, and customer engagement
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Ensure 100% compliance with safety, loss prevention, and organizational policies
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Lead annual reviews of audits, procedures, and risk controls in partnership with HR and Loss Prevention
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Partner closely with Finance, eCommerce, Operations & Sustainability, Real Estate, and other departments
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Lead cross‑functional initiatives that drive alignment, transparency, and shared accountability
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High school diploma or GED (required)
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8–10 years of progressive retail leadership experience, including multi‑unit oversight
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Demonstrated success leading large, complex, multi‑site retail operations
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Strong executive‑level decision‑making and people leadership experience
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Bachelor’s degree in business, retail management, or a related field
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Experience scaling operations, improving underperforming locations, and leading enterprise initiatives
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Strategic, visionary leadership with strong execution capability
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Advanced financial and operational acumen
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Executive presence and ability to influence at all organizational levels
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Strong cross‑functional collaborator and relationship builder
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Data‑driven decision‑maker with a bias toward action
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Commitment to diversity, equity, inclusion, and community impact
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Combination of office and retail environments
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Regular travel throughout Goodwill’s service territory (Maryland and Eastern Shore)
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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/
EOE – Including Disability/Veterans
