Life as a Chief of Staff Managing Multiple Estates
When most people think about household staff, they might picture a single housekeeper or nanny working in one home. But at the very top of the domestic staffing hierarchy sits a role that’s equal parts CEO, diplomatic ambassador, and master conductor: the Chief of Staff. These exceptional professionals manage not just one household, but entire portfolios of properties spanning cities, states, and sometimes even countries.
At Seaside Staffing Company, we’ve had the privilege of placing Chief of Staff professionals with some of the world’s most discerning families. What makes this role so unique isn’t just the scale of responsibility, but the incredible journey these professionals take to reach this pinnacle position in our industry.
The Career Path to Becoming a Chief of Staff
The path to becoming a Chief of Staff doesn’t happen overnight. Our industry has a beautiful progression that allows talented individuals to grow and develop their skills over time. Many of our most successful Chief of Staff placements started their careers as house managers, overseeing the daily operations of a single family home. From there, they might advance to property manager roles, gaining experience in maintaining and coordinating multiple aspects of real estate management.
The next step often involves becoming an estate manager, where professionals learn to oversee larger properties with multiple buildings, extensive grounds, and larger staff teams. These estate managers develop the leadership skills, vendor management expertise, and strategic thinking that makes them ideal candidates for Chief of Staff positions when families expand their property portfolios.
What Ultra High Net Worth Families Need from a Chief of Staff
The families who employ Chief of Staff professionals typically have net worth exceeding $100 million. These might be Fortune 500 CEOs, professional athletes, entertainment celebrities, or generational wealth families who’ve built business empires. When your family owns a penthouse in Manhattan, a compound in the Hamptons, a ski lodge in Aspen, and a vineyard in Napa Valley, you need someone who can seamlessly coordinate operations across all these properties.
A Chief of Staff becomes the central nervous system for these complex household operations. They’re traveling ahead of the family to ensure the London flat is perfectly prepared for a two-week stay, coordinating with local staff to stock the kitchen with the children’s favorite snacks, and ensuring the family’s preferred linens are waiting in the master suite. Meanwhile, they’re also overseeing routine maintenance at the other properties, managing staff schedules, and perhaps coordinating with the family office on upcoming events or renovations.
The Daily Reality of Managing Multiple Estates
No two days are alike when you’re a Chief of Staff managing multiple properties. One morning might start with a video call to the house manager at the Malibu beach house about preparing for a last-minute family gathering. By afternoon, you might be reviewing security protocols with the team at the family’s European estate before a high-profile visit. The evening could involve coordinating with contractors about a kitchen renovation at the family’s primary residence.
Technology plays a crucial role in managing this complexity. Chief of Staff professionals become experts in project management software, communication platforms, and digital systems that help them stay connected with staff teams across different time zones. They maintain detailed household manuals for each property, ensuring consistency in service standards whether the family is waking up in their Manhattan penthouse or their Jackson Hole retreat.
The role requires incredible adaptability and cultural sensitivity, especially when managing international properties. A Chief of Staff might need to understand local employment laws in multiple countries, work with vendors who speak different languages, and ensure that each property reflects both the family’s preferences and local customs.
At Seaside Staffing Company, we understand that finding the right Chief of Staff is about more than just checking boxes on a resume. It’s about finding someone who can become a trusted extension of the family itself, someone who understands that managing multiple estates isn’t just about logistics, it’s about creating homes where families can focus on what matters most, no matter where in the world they are.
The Chief of Staff role represents the pinnacle of domestic staffing excellence, and for the right professional, it offers an incredibly rewarding career path that combines strategic thinking, people management, and the satisfaction of creating extraordinary experiences for families across their entire portfolio of properties.
