Senior Director of Retail

GOODWILL IND OF THE CHESAPEAKE INC•Arbutus, MD

12d•$110,000 - $140,000

About The Position

The Senior Director of Retail has a strategic role responsible for leading the vision, performance, and alignment of the organization’s retail operations. Overseeing donation processing, merchandising, sales, customer experience, and talent development, this role drives innovation, financial stewardship, and cross-functional collaboration. With both strategic foresight and operational agility, the Senior Director influences organizational direction, positions retail as a catalyst for mission advancement and sustainable growth, and partners with leaders across eCommerce, Operations & Sustainability, and other departments to align retail with long-term strategy.

Requirements

High School diploma/GED is required; a bachelor’s degree in business, retail management, or related discipline is strongly preferred
Minimum of 8–10 years of progressive retail leadership experience, including multi-unit management, strategic planning, and executive-level decision-making.
Demonstrated experience leading large teams and managing complex, multi-site operations
Must possess a valid, unrestricted driver’s license and meet Maryland insurance requirements.
Visionary leadership with the ability to translate strategic goals into operational success.
Executive presence with the ability to influence, inspire, and align diverse stakeholders.
Strong financial acumen, including budgeting, forecasting, and performance analysis.
Demonstrated ability to build and sustain collaborative relationships across departments and organizational levels.
High level of initiative, with a proactive approach to innovation, problem-solving, and execution.
Skilled in coaching and developing high-performing, cross-functional teams.
Excellent communication, negotiation, and interpersonal skills.
Proficient in Microsoft Office Suite and retail management systems.
Deep understanding of merchandising principles, customer engagement, and market dynamics.
Commitment to diversity, equity, and inclusion, with the ability to lead diverse teams and serve diverse communities.

Responsibilities

Provide organizational-level leadership and oversight for all retail operations, ensuring alignment with mission, financial goals, and community impact.
Develop and execute strategies that drive 8–12% year-over-year sales growth, leveraging data and market insights.
Ensure production targets are consistently met across the organization, maintaining 100% achievement, while sustaining textile sell-through rates at or above 50% to guarantee high-quality merchandise and support a 5% increase in average transaction value. Drive company-wide round-up participation to a minimum of 40%, reinforcing our commitment to community support and engagement.
Develop and manage multi-million-dollar budgets, analyze financial performance, and drive profitability through data-informed decision-making, maintaining financial performance within ±5% of budget.
Contribute to organization-wide strategic planning and policy development, launching at least 2 major initiatives annually to enhance efficiency or customer experience.
Collaborate with real estate and executive leadership to evaluate and select new store locations using market intelligence, demographic analysis, and long-range forecasting.
Lead execution of organizational initiatives by identifying trends, proposing solutions, and driving results with urgency and ownership.
Oversee store performance, implementing strategies to improve productivity, customer satisfaction, and revenue; achieve 10%+ improvement in underperforming stores within 90 days.
Represent retail operations in board-level discussions and cross-functional leadership forums.
Build and lead a high-performing team culture focused on innovation, accountability, and continuous improvement.
Strengthen leadership pipeline through coaching, training, and succession planning; increase internal promotion rates year-over-year.
Partner with HR to maintain store-level vacancy rates below 15% and empower managers to lead with influence and cross-functional collaboration.
Ensure consistent, high-quality customer service across all locations; reduce complaints annually through proactive training and resolution.
Maintain brand integrity and ensure stores are consistently stocked with high-quality, mission-aligned products through effective merchandising strategies, ensuring 100% implementation of seasonal plans and promotional campaigns.
Ensure 100% compliance with safety, loss prevention, and company policies through audits, training, and proactive risk mitigation.
Lead annual reviews of retail audits and procedures, partnering with HR and Loss Prevention, and other departments as needed to collaboratively review and update documents.
Foster strong partnerships with internal stakeholders including Finance, eCommerce, Operations & Sustainability, and other departments to align retail strategies.
Lead cross-functional meetings and training sessions to promote transparency, alignment, and shared accountability.