Senior Director of Retail

GOODWILL IND OF THE CHESAPEAKE INC•Arbutus, MD

3d•$120,000 - $150,000

About The Position

Goodwill Industries of the Chesapeake is seeking a Senior Director of Retail to provide enterprise-level leadership for a multi-site retail operation that funds mission programs across the community. The role sets strategic direction for store performance, merchandising, production, customer experience, and retail talent development, positioning retail as a driver of organizational growth, financial sustainability, and mission impact. The Senior Director leads strategy, execution, and cross-functional alignment across the retail footprint to ensure stores operate efficiently, perform strongly, and deliver an exceptional customer experience while advancing workforce development and community outcomes. The role combines strategic vision with operational leadership and partners closely with executive leadership and departments including eCommerce, Finance, Operations & Sustainability, and Real Estate.

Requirements

High school diploma or GED.
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.
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 collaboration and relationship-building skills.
Data-driven decision-making and a bias toward action.
Commitment to diversity, equity, inclusion, and community impact.
Access to a personal vehicle is required.

Nice To Haves

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

Responsibilities

Lead the overall strategy, performance, and alignment of 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 achievement of production targets while maintaining textile sell-through rates above 50%.
Increase average transaction value by 5% through merchandising and pricing strategies.
Lead company-wide initiatives to increase customer engagement, including sustaining round-up participation above 40%.
Oversee store performance and address underperformance, achieving improvements of 10% or more 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 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 with Finance, eCommerce, Operations & Sustainability, Real Estate, and other departments.
Lead cross-functional initiatives that drive alignment, transparency, and shared accountability.