Retail Business Director (Chief of Staff to President, Retail)

Pilot Company•Knoxville, TN

6d•Onsite

About The Position

The Chief of Staff to the President, Retail serves as a strategic advisor, integrator, and execution partner to ensure alignment, momentum, and impact across the Retail organization. This role drives clarity, prioritization, and cross-functional collaboration, enabling the President, Retail to focus on the most critical decisions and initiatives. Operating with high influence, the Chief of Staff leads through relationships, structured thinking, and disciplined program management.

Requirements

Systematic Thinker: Able to break down complexity, build structure, and drive clarity across ambiguous or evolving priorities.
Data-Driven: Leverages analytics and insights to inform recommendations, measure impact, and guide decision-making.
Strong Project Management: Highly organized, disciplined, and adept at moving multiple initiatives forward simultaneously.
Organizational Influence: Leads through credibility, communication, and relationship-building—without authority or direct reports.
Trust & Confidence Builder: Earns the confidence of senior leaders and partners through integrity, judgment, discretion, and dependable follow-through.
Minimum of five years of business experience
Experience in both strategic and tactical operational roles
Prior leadership experience and a demonstrated ability to lead via influence
MBA or equivalent

Nice To Haves

Prior experience in the retail industry strongly preferred
Prior chief of staff experience preferred

Responsibilities

Strategic Planning & Initiative Leadership Act as a strategic partner for the president of retail related to targeted initiatives and help set direction for the retail leadership team.
Facilitate the development of strategic priorities, long-range planning, and the Retail organization’s agenda for key initiatives.
Track and report on Retail KPIs, partnering with business owners to ensure execution on special projects that drive performance.
Review, assess, and evaluate key areas of the retail business by conducting root cause analysis of issues, finding solutions, and implementing efficient changes needed to drive results across teams.
Execution & Project Facilitation Establish governance, common processes, tools, metrics and resources needed to successfully execute against retail KPIs.
Advise, organize, and facilitate execution of critical projects, ensuring they deliver measurable impact.
Stay closely connected to Retail initiatives, proactively identifying roadblocks, driving solutions, and flagging risks or slippage to the President, Retail.
Coordinate with adjacent functional leaders to strengthen cross-functional alignment and drive shared outcomes.
Leadership Support & Organizational Alignment Represent the president, retail in key meetings as needed, ensuring continuity of leadership presence and decision-making.
Support overall administration of the president’s calendar, ensuring prioritization, preparedness, and anticipation of needs.
Serve as a connector and influencer across the retail organization, convening stakeholders and shaping perspectives to align with retail goals