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Join a leading vacation rental management company that oversees more than 10,000 properties across premier resort locations nationwide. This is a rare opportunity to step into a hands-on, accelerated leadership track designed to groom the next generation of senior executives. Experience rapid career growth, meaningful impact, and a mission-driven culture built on servant leadership, ownership mentality, and operational excellence.
President-in-Training Benefits & Compensation
- Competitive base salary with annual performance bonus
- Comprehensive health insurance coverage
- 401(k) retirement plan with company match
- Full relocation support for final Brand President placement
- Immersive executive development, mentorship, and measurable pathway to senior leadership
President-in-Training Requirements & Qualifications
- 2–5 years in management, private equity operations, corporate strategy, or similar high-performance environments
- 3+ years in operations, hospitality, logistics, retail leadership, or general management roles
- Prior experience managing people or cross-functional teams strongly preferred
- Bachelor’s degree required; MBA or relevant graduate degree strongly preferred
- Strong analytical, communication, and project management skills
- Willingness to relocate for future Brand President assignment
President-in-Training Preferred Background & Skills
- Experience leading cross-functional initiatives and driving results without formal authority
- High emotional intelligence and a coaching leadership style
- Comfort with ambiguity, rapid change, and hands-on execution
- Alignment with a mission-driven, high-growth culture
President-in-Training Day-to-Day Responsibilities
- Serve as the #2 leader in a complex or high-growth vacation rental business
- Drive execution and ongoing improvement across guest services, housekeeping, maintenance, and owner services
- Motivate, manage, and develop frontline leaders and their teams
- Lead weekly business reviews; collaborate with centralized support functions
- Shadow senior executives and participate in focused leadership workshops
- Own key performance outcomes in guest satisfaction, owner retention, team engagement, and profitability
- Prepare to assume full P&L responsibility and transition into a Brand President role
This unique, field-based apprenticeship offers the hands-on learning, mentorship, and operational immersion needed to lead the future of hospitality.
JOB ID: 180017
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Melissa Montero