Holidays in High Season: Insights from a CEO

The Path from Entrepreneur to CEO in Property Management

When I began my journey as a property manager, I found myself in uncharted territory. There was scarce information relevant to my field, and few shared my path. Yet, my approach was simple: face challenges head-on and show up every day. This persistence was key to moving forward, as I thrived on identifying issues and crafting solutions.

A significant turning point came when I met two mentors who had carved their own paths to success. Their advice was clear and game-changing: step back from day-to-day operations. Initially, this seemed impossible since our clients were deeply connected with me personally, not just with Costarentals. It quickly became apparent that being synonymous with the brand was unsustainable if we wanted to
expand—clients’ dependence on me was a bottleneck.

Structural Transformation and Growth

Years passed, and we grew from managing 20 properties to 200, even navigating through the challenges of COVID-19. This expansion was fueled by a strategic overhaul of our company structure. When my business partner, who had been with the company from the start, departed, it was an opportunity to establish specialized departments.

I set up a front desk department, led by a manager who reported directly to me. This new structure streamlined our Airbnb and OTA communications significantly. Concurrently, we recruited an experienced operations manager responsible for all field activities, including property checks before and after guest stays.

Despite these improvements, client engagement and owner onboarding remained predominantly my responsibility, given the success I had in securing new contracts. To address this, I delegated these tasks to my most trusted colleague, who assumed the role of sales manager effectively. This move proved pivotal, allowing the sales manager to handle all new inquiries while I continued managing relationships with
our existing 200+ property owners.

To further streamline operations, we introduced the “Owner Experience” department—akin to what others might call key account management. This department centralized communication, reducing confusion and enhancing satisfaction by providing owners with a single point of contact for their needs.

Ensuring Sustainability and Continuity

Each department head was empowered to manage their team autonomously, from hiring to vacation planning and maintaining high standards of performance. This autonomy ensures that each department can innovate and optimize without
constant oversight.

A contingency plan is essential for sustainability. Should a manager depart, we have groomed senior staff within each department who can step into leadership roles. This strategy not only minimizes disruption but also promotes longevity and loyalty
among staff, keeping turnover low.

A CEO’s Focus

Today, my role is predominantly supervisory. I support our managers and provide insight into their decisions, allowing me to concentrate on broader strategic goals like system implementation, identifying weaknesses, and preemptive
problem-solving. My principal aim is to enhance efficiency across departments without compromising quality.

By stepping back, I have gained a clearer perspective—sometimes, quite literally from
a holiday vantage point. This shift not only allows me to lead more effectively but
also underscores the importance of structuring a company that thrives on delegation
and specialized expertise.