Senior Director of Retail

Senior Director of Retail

$120,000-150,000 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/

EOE – Including Disability/Veterans