Professionally nannying for ultra-wealthy families has turned Cassidy O’Hagan into a jet-setter with perks most people only dream about. At just 28 and based in Colorado, she’s been paid to spend winters in Aspen, summers in the Hamptons, and travel everywhere from Puerto Rico to Dubai and across Europe on luxury yachts—all while working. Last December, she was in the Maldives, staying in a private villa at an exclusive resort, with chef-made meals, a dedicated wardrobe, and globe-trotting via private jets—all simply part of the job.
Her role comes with a six-figure salary, complete benefits, paid time off, and extras like chauffeurs and a “nanny wardrobe”—far surpassing the orthopedic medical sales job she’d once envisioned. “My old corporate healthcare gig just couldn’t compete, not in money or lifestyle,” O’Hagan says. After spending time in medical offices and sales, she realized nannying for ultra-rich families was in another league.
The Private Staffing Boom
“Private staffing” supports the lavish lifestyles of today’s rich—think nannies, chefs, security guards, executive assistants, and house managers. For many young professionals, these jobs are more lucrative, glamorous, and flexible than the traditional corporate climb. According to Brian Daniel, founder of Celebrity Personal Assistant Network, private staffing agencies have exploded from a few specialists to about 1,000 worldwide, half of which are in the US. “Every billionaire employs small armies to cater to their every need. The demand is huge, and the wealth is staggering,” Daniel says.
The growth of both billionaires and millionaires means more mansions, jets, and yachts need staffing. Salaries and perks have soared as wealthy families compete to attract the best talent. A recent browse through Tiger Recruitment revealed salaries such as $120,000 for housekeepers, $150,000 for nannies, $250,000-$280,000 for chief assistants, and $200,000-$250,000 for directors of residence. Perks include guest houses, company cars, guaranteed hours, and 401Ks.
Gen Z's Corporate Exodus
O’Hagan first tried nannying while prepping for the MCAT at age 22. She quickly realized how different life was in a billionaire’s mansion, where “covered meals” meant an on-site chef feeding both family and staff, and she was part of a “childcare team” alongside personal assistants and a home chief of staff. Yet, she still felt pressure to pursue her healthcare ambitions—until a stint in New York’s medical sales left her burnt out and invisible on a $65,000 salary.
“In the end, I walked away from the work that actually fit who I am—nurturing, intuitive, service-based,” she says. She returned to nannying, this time targeting families at the top of the wealth pyramid. Immediately, her income jumped $40K, and benefits multiplied: chef-cooked meals, a full wardrobe, and employer-paid ride shares. It was “night and day” compared to the corporate grind.
Gen Z is increasingly disenchanted with climbing the corporate ladder. A 2025 Deloitte survey found just 6% want a leadership role, while many avoid management altogether in favor of work-life balance. Still, they expect high compensation—an Empower survey pegged Gen Z’s version of “financial success” at nearly $600,000 a year, six times more than Boomers. Yet, hiring has slowed, and AI is transforming office roles.
Now, private staffing attracts overqualified applicants—PhDs, lawyers, business owners, and even those from real estate. “The industry’s gotten much younger and more educated,” Daniel says.
High Compensation, High Pressure
For those willing to work long hours and put their clients—known as “principals”—first, private service roles pay extremely well. Julia Dudley, 26, left communications and culinary school to run her own meal prep business and cook as a private chef for Hamptons families. “I make my own hours, as much or more money, and I’m my own boss. Private service is much better than the restaurant grind,” she says.
Brian Daniel notes that skilled staff can triple their earnings compared to high-end restaurants. But the jobs are demanding—energy, round-the-clock availability, and absolute discretion are required. NDAs and clean social media profiles are standard. “The stress can be more than Wall Street,” Daniel admits, recounting panic attacks from the pressure.
Pros like O’Hagan work across multiple homes worldwide, living alongside families and their private routines—sometimes feeling isolated as personal and professional worlds blend. Major holidays are often spent with the families they serve rather than their own.
Breaking Into the Industry
Getting in isn’t easy. Agencies do most of the recruiting, and representation is often required to even meet a client. But excellence gets recognized: Daniel’s example of a Hollywood driver rising to become an assistant, then a co-producer earning “fabulous money,” illustrates the potential for advancement.
O’Hagan is now starting her own coaching and staffing business to help others break in. Her peers, many dissatisfied in corporate jobs, reach out for advice. She even inspired her brother to switch from media to assist a celebrity esthetician. Others have found meaning and stability—like Edwards’ son, who went from office work to working as a deckhand on a superyacht.
“This career has given me stability and a level of personal connection I hadn’t found anywhere else,” O’Hagan says. For Gen Z and others rethinking work, private service for the wealthy offers something the corporate world increasingly can’t: high pay, memorable experiences, and direct impact—if you’re up for the intensity and discretion required.