Senior Director of Retail

Senior Director of Retail Goodwill Industries of the Chesapeake, Inc. $110,000-140,000 - Bonus Eligibility United States, Maryland, Halethorpe May 20, 2026 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. Why This Role Matters 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. Key Responsibilities Enterprise Retail Leadership 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
Financial & Performance Management 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
Operational Oversight & Execution 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
Leadership Development & Workforce Strategy 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%
Customer Experience & Brand Integrity 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
Compliance & Risk Management 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
Cross-Functional Collaboration Partner closely with Finance, eCommerce, Operations & Sustainability, Real Estate, and other departments
Lead cross-functional initiatives that drive alignment, transparency, and shared accountability
What We're Looking For Required Qualifications 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
Preferred Qualifications Bachelor's degree in business, retail management, or a related field
Experience scaling operations, improving underperforming locations, and leading enterprise initiatives
Leadership Competencies 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
Work Environment & Travel Combination of office and retail environments
Regular travel throughout Goodwill's service territory (Maryland and Eastern Shore)
Access to a personal vehicle required
Why Goodwill? 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/