Director Of Strategy
The Director of Strategy leads the design and execution of high-impact corporate initiatives across the timeshare, recreation / leisure, and real estate development businesses. The role is accountable for identifying viable alternatives, creating and shaping actionable strategies, and driving implementation while managing external consultants and vendors. Alternatives recommended will be driven by researching challenges, drivers, and solutions, along with competitive landscape and possible partners.
Serving as a critical bridge between executive leadership and functional teams, the Director ensures cross-division alignment and seamless execution of strategic priorities. Core responsibilities include conducting feasibility studies and financial modeling to support new club development and evaluating and implementing strategic partnerships to identify clear opportunities for growth and design appropriate risk mitigation strategies and successful transition pathways. Partners will include necessary vendors to enable back-of-house operational needs and to provide customer-facing technology as well as regional or national business partners whose participation could accelerate adoption and utilization of new products / initiatives.
The position also advances timeshare product strategy by overseeing overall pricing strategy, regular repricing, product-line mix decisions, and coordination with Finance on cost of goods sold and profitability targets. Additional focus areas include asset management strategies and hospitality / commercial property rollout, ensuring the company's development and product portfolios are positioned for long-term value creation.
Success in this role is measured by the delivery of timely and accurate financial models, feasibility studies, transition plans, and launch-ready strategies that equip the Board with clear options and support sustainable revenue growth. Success will require designing and implementing successful pilots and A : B testing programs.
Preferred experience includes a proven background in hospitality, timeshare, recreation / leisure, or real estate development. Deep understanding of timeshare exchange platforms and their trends, membership / club models, inventory utilization and balanced trading, and associated revenue and profitability streams (including margins and ROI). Demonstrated expertise in managing partner relationships, deal negotiation, and contract management, with experience creating Board level reports on those topics.
Strong foundation in Financial Planning & Analysis (including advanced margin and fixed / variable cost analysis) and the creation of Board-ready financial reports, recommendations, and presentations. Bachelor's degree in a relevant discipline required; MBA or equivalent professional certification preferred. Proven executive leadership experience with a steady record of advancement and successful team or project oversight.
Director Of Strategy • Charlottesville, VA, US