President in Training

Location: Remote to start; relocation required to one of the company's operating markets (beach towns in the Southeast or premier vacation destinations in the West, such as Tampa, Destin, Scottsdale, or Steamboat)
Program Duration: 12–18 months
Compensation: $125,000–$150,000 base salary + bonus + long-term incentive eligibility

The company is a leading vacation rental management platform in the United States, managing 10,000+ vacation rentals across top resort destinations. The business is growing rapidly, gaining market share, and redefining the industry through locally led operations, industry-leading operating practices, and a strong learning and performance culture.

The organization is deeply committed to delivering exceptional service to property owners and memorable guest experiences, while building scalable, high-performance local businesses.

The President-in-Training – Operations Immersion Track is a hands-on, field-based leadership apprenticeship designed to develop future Brand Presidents through deep operational ownership and team leadership.

Over 12–18 months, participants will operate as the #2 leader within one of the company's most complex or high-growth markets. You'll gain end-to-end exposure to daily operations, people leadership, financial performance, and local market strategy—building the skills and judgment required to run a full P&L.

This program is ideal for high-potential operators looking to accelerate their path to general management in a mission-driven, high-performance environment.

• Drive execution across core operational functions, including guest services, housekeeping, maintenance, and owner services

• Lead department heads and ensure performance against key metrics

• Maintain alignment with company SOPs, systems, and technology platforms

• Lead weekly business reviews and collaborate closely with centralized support teams

• Hire, manage, and develop frontline leaders and individual contributors

• Build and reinforce a culture of ownership, excellence, and servant leadership

• Act as a visible, hands-on leader who sets high standards for accountability and performance

• Support local market strategy and execution alongside the Brand President

• Support owner acquisition and retention initiatives

• Lead special projects focused on improving efficiency, margins, and service quality

• Identify and execute opportunities to strengthen local operations and customer experience

• Participate in formal training forums and leadership workshops

• Shadow senior executives and attend strategic planning sessions

• Build the judgment, discipline, and confidence required to run a scaled local business

• Learn to lead with company culture and values at the core

By the end of the program, you will be expected to:

• Own and improve key KPIs across guest satisfaction, owner retention, team engagement, and EBITDA

• Demonstrate readiness to assume full P&L responsibility

• Seamlessly transition into a Brand President role with confidence and operational fluency

• Lead a local business with strong people leadership, operational rigor, and market expertise

• 2–5 years in management consulting, private equity operations, corporate strategy, or similar high-performance environments

• 3+ years in operations, hospitality, logistics, retail leadership, or general management roles

• Bachelor's degree required

• Strong analytical, communication, and project management skills

• Comfort operating in ambiguous, fast-paced environments

• Ability to drive outcomes across teams without formal authority

• Highly driven, curious, and execution-oriented

• Strong people leader with high emotional intelligence and a coaching mindset

• Bias for action, operational discipline, and resourcefulness

• Comfortable with hands-on execution, rapid change, and relocation

• Willingness to relocate for final Brand President placement (relocation support provided)

• Prior people management and cross-functional leadership experience strongly preferred

• MBA or relevant graduate degree strongly preferred

• Base salary: $125,000–$150,000 annually

• Annual performance bonus: Up to 10% of base salary, tied to key business KPIs

• Comprehensive health insurance benefits

• 401(k) retirement plan with company match

• Full relocation support for Brand President placement

• Upon promotion to Brand President:

  • Participation in the company's long-term incentive program

  • Eligibility to earn 12.5% of EBITDA growth from start date through recapitalization