This is a remote position.

Role: President-in-Training – Operations Immersion

The company is a leading vacation rental management company in the United States, managing over 10,000 vacation rentals across premier resort locations, growing rapidly and gaining market share. We are committed to delivering exceptional service to property owners and unforgettable experiences to guests, as well as innovating the industry model to focus on local operations turbocharged by industry-leading operating practices and a relentless learning culture.

Job Summary

The President-in-Training – Operations Immersion Track is a hands-on, field-based apprenticeship designed to develop the next generation of Brand Presidents through deep operational experience and team leadership. Over 12–18 months, participants will act as the #2 leader in one of the company's most complex or high-growth businesses, learning the full scope of day-to-day operations, leadership, and local market dynamics.

This track builds operational muscle, people management skills, and market fluency—creating a strong foundation to lead one of our local brands upon graduation.

This program is ideal for experienced operators looking to accelerate their careers through immersive leadership training in a high-performance, mission-driven environment.

Location:
You will start out working remotely, then move to one of the company's locations in a beach town in the southeast or to a popular vacation town in the west i.e. Tampa, Destin, Scottsdale, Steamboat.

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  Own and improve critical KPIs in guest satisfaction, owner retention, team engagement, and EBITDA performance
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  Lead operational departments (guest services, housekeeping, maintenance, owner services) under guidance of the Brand President
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  Develop strong local leadership and team-building experience
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  Build and demonstrate readiness to assume full P&L leadership as a Brand President
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  Seamlessly transition into a Brand President role with the confidence and context to lead

Key Responsibilities

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  Operational Excellence
  • 
    We define operational excellence as Customer Obsession + P&L Management + Constant Improvement
  • 
    Drive execution across core operational functions including field teams, owner services, guest experience, and housekeeping
  • 
    Manage department heads and ensure performance metrics are met
  • 
    Maintain operational alignment with company's SOPs and technology solutions
  • 
    Lead weekly business reviews and collaborate with centralized functions
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  Team Leadership
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    Hire, manage, and develop frontline leaders and individual contributors
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    Drive team culture based on company’s values of ownership, excellence, and servant leadership
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    Serve as a visible, accessible leader who sets a high standard of performance and accountability

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  Support local market strategy and execution with the Brand President

• • 
    Help drive owner acquisition and retention initiatives
  • 
    Lead special projects to improve efficiency, margin, and service quality
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  Executive Preparation
  • 
    Attend training forums and workshops as part of the Brand President development track
  • 
    Build the judgment, operating discipline, and leadership confidence required to run a full P&L
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  Leadership Development
  • 
    Shadow senior executives and attend key strategic forums
  • 
    Learn to lead with company’s culture and values at the core
  • 
    Build the judgment, perspective, and operating knowledge to run a vacation rental business while driving growth and performance

Qualifications

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  Experience:
  
  • 
    2–5 years in management consulting, private equity operations, corporate strategy, or related high-performance environments
  • 
    3+ years in operations, hospitality, logistics, retail leadership, or general management roles
  • 
    Prior experience managing people and cross-functional teams strongly preferred
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  Education:
  
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    Bachelor's degree required; MBA or relevant graduate degree strongly preferred
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  Skills:
  
  • 
    Strong analytical, communication, and project management skills
  • 
    Comfort with ambiguity and fast-paced environments
  • 
    Ability to lead cross-functional initiatives and drive outcomes without formal authority
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  Personal Attributes:
  
  • 
    Highly driven, humble, curious, and execution-oriented
  • 
    Strong alignment with Awayday’s values and leadership philosophy
  • 
    Willingness to relocate for final Brand President placement (relocation expenses covered)
  • 
    Strong people leader with high emotional intelligence and a coaching mindset
  • 
    Bias for action, operational discipline, and resourcefulness
  • 
    Comfortable with ambiguity, rapid change, and hands-on execution

Compensation and Benefits

• 
  The position offers a base salary of
  125-150k
  annually, together with comprehensive health insurance benefits and a matching 401(k) retirement plan.
• 
  In addition to a competitive base salary, the President In-Training is eligible for a performance-based annual bonus of up to 10% of base salary tied to key business performance indicators.
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  Full relocation support for Brand President placement at end of program
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  Upon promotion to Brand President, participation in company's long-term incentive program, including eligibility to earn 12.5% of the EBITDA growth from start date through recapitalization.