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When Cassidy O'Hagan looked out over the crystal blue water in the Maldives last December, she felt like she'd made it. The 28-year-old was staying in an ultra-exclusive resort, in her own private villa. And for her, this was work. Nannying for ultra-wealthy families has brought the Colorado native to places she never dreamed she'd go: winters in Aspen, summers in the Hamptons, trips to Puerto Rico, India, and Dubai, and traversing European waters on what she calls a "mega, mega yacht." O'Hagan has a 401K, healthcare benefits, PTO, and a six-figure salary (she declined to specify per her NDA but said it was between $150,000 and $250,000). That's not to mention other perks like meals cooked by a private chef, her own "nanny wardrobe," access to personal chauffeurs, and trotting the globe via private jet. "My orthopedic medical sales job could never compete," she says. She imagined by this point in her life she'd be wrapping up medical school. But in 2021, after post-grad stints in doctor's offices and corporate healthcare, she ditched those plans and joined a growing wave of Gen Zers who are fleeing white-collar life in favor of working for the homes and estates of the ultrarich. "Private staffing" is the intricate personnel infrastructure that quietly makes the lavish lives of the wealthy so lavish. Think nannies, executive assistants, personal assistants, house managers, butlers, security staff, chauffeurs, and personal chefs. For many young people, it's a more in-demand, lucrative, sexy, and dynamic alternative to climbing an increasingly wobbly corporate ladder. When Brian Daniel started his staffing agency, the Celebrity Personal Assistant Network, in 2007, he was one of the few specialists for the super rich around, he says. Today, he estimates there are about 1,000 private staffing agencies globally, about 500 of which are in the US. "The appetite is insatiable," he says. "The depth and the breadth of the wealth is just so staggering." In this winner-take-all era of capitalism — a time when tech companies are dangling nine-figure offerings to top AI researchers and Elon Musk is on pace to become the world's first trillionaire, while career paths crumble and mass layoffs rip through the white-collar world — many Gen Zers are looking to today's ultra elite and deciding that if you can't beat them, pamper them. In 2000, there were 322 people on Forbes' list of billionaires in the world; today there are more than 3,000. There's also what a recent UBS report called "the rise of the everyday millionaire" — the number of people globally with $1 to $5 million in investable assets has quadrupled to 52 million in the last 25 years. As the megarich have multiplied, so too have their mansions, planes, and yachts that need to be staffed. "There are so many wealthy people, and they're not just buying one estate," Daniel tells me. "There's never been a better opportunity in history to get into private service, because each one of these billionaires employs small armies of people to cater to their every whim." A post-pandemic hiring spree has also created bidding wars within the industry, driving up salaries and perks. "There's a very severe shortage across the board of elite staff," Daniel says. "Oh, you need a place to stay? Here's the guest house. Oh, you need a company car? Here you go. A 401k, guaranteed hours — I mean, they're throwing in the kitchen sink." A recent look at open roles on the staffing agency Tiger Recruitment's website was illustrative. There was a listing for a housekeeper that pays up to $120,000, and a nanny that pays up to $150,000. There was a "head of personal assistants" with a salary range of $250,000 to $280,000 and a "director of residences" that jets between properties in New York, East Hampton, Aspen, and Bel Air for $200,000 to $250,000. Related stories Business Insider tells the innovative stories you want to know Business Insider tells the innovative stories you want to know When O'Hagan started looking to work for a high-net-worth family in 2019, she was 22 and looking to earn extra money while preparing for the MCAT. Soon after landing her first job, she says, "I realized very quickly after moving in that I had stepped into this completely different world." Oh, you need a place to stay? Here's the guest house. Oh, you need a company car? Here you go. A 401k, guaranteed hours.Brian Daniel, founder of the Celebrity Personal Assistant Network Details in the interview were scant, but when she arrived at the family's California mansion she learned that "covered meals" in the job description turned out to mean an in-house chef who not only cooked on-site for the family, but for an entire domestic staff. O'Hagan was one of four nannies on a "childcare team" working for a couple in their mid-30s from a big-name business family. There were personal assistants, a roster of housekeepers, a chief of staff of the home, and even a dedicated home organizer. Satisfying as the work was, she still planned to build a career in healthcare. "I definitely had internalized this message that no matter how professional or demanding or meaningful my job was, being a nanny was just not enough. So I kind of forced myself into corporate life," she says. In 2021, she moved to New York City for a job in medical sales at a large company. She spent long hours in surgeries and at hospitals in a "very male-dominated" environment, O'Hagan says. Her entry-level $65,000 salary also didn't go very far in the city. Soon, she felt burnt out and invisible. "I realized that I had walked away from work that actually aligned with who I was," she says, "someone who's very nurturing and personable and intuitive and service based." After less than a year, she quit and got back into nannying — this time with the intention to build a career and work for families who were next-level wealthy. "Being in New York, I knew there are billionaires here, there are ultra high net worth families here," she says. "I was really wanting to go to the top." She started working with private staffing agencies, and landed a rotational nanny position with what she describes as a well-known New York family. Her income went up by $40K instantly. She also had chef-made meals again, an entire wardrobe provided to her by the family, and got to ditch the subway thanks to covered Uber rides to and from work. It was "a night and day" switch from the corporate grind — and she hasn't looked back. As Gen Z has grown more disillusioned with corporate life, O'Hagan is far from alone in her pivot. A 2025 Deloitte survey found that only 6% of Gen Zers say their primary career goal is to reach a leadership position at work. Some are even avoiding taking on managerial roles at all (it's called "conscious unbossing") to prioritize work-life balance. At the same time, they also expect to earn more, a lot more, than older generations. Per a recent Empower survey, Gen Zers define financial success as a salary of nearly $600,000, about six times higher than what Boomers said. And yet, post-grads have been particularly vocal about their inability to get jobs as hiring across US has reached a lull in recent months and AI continues to creep into corporate strategy. Private staffing has always been a career that people sort of fall into, says Daniel. What's different today, is "not only are the newer players these days in the industry younger, they're college educated," he says. "I get emails from people who have PhDs, people who were lawyers, people who were business owners, people who were in real estate." The stress can be more than even on Wall Street.Brian Daniel Among the newcomers is Julia Dudley. The 26-year-old got her undergrad and master's degree in communications — and then went to culinary school. But she eventually ditched both agency and restaurant work in favor of building a meal prep business and working as a private chef. "I was like, okay, I can make my own hours, I can make more money, I'm my own boss," she says. "This is way more interesting to me than being on the line" in a restaurant. She has spent the last few summers cooking for families in the Hamptons, where she says cooking two or three meals a day for a few months can pay a six-figure salary. Related stories Business Insider tells the innovative stories you want to know Business Insider tells the innovative stories you want to know "A lot of chefs will leave the five star restaurant and go into private service," says Daniel. "We know how long and grueling it can be, but you can triple your salary by leaving the restaurant and going into private service and working for a billionaire." Working for a billionaire can also be nerve-racking. "The reason you're paid well is because you're expected to be on call outside the usual 9-to-5 in a lot of these roles, and sometimes you'll be expected to work long hours," says Ruth Edwards, a private staffing recruiter at Tiger who specializes in family offices and private residences of ultra-high-net-worth clients. "In this industry with the celebrities and billionaires, you have to have a lot of energy because it's always breakneck speeds," says Daniel. You must be willing to do whatever is necessary to help the "principle," the industry term for the client. "If the housekeeper went home and the dog did some doo-doo in the living room and you're there with the VIP, somebody has to do it," he says. "Then what happens is, you do something like that, and 30 minutes later or an hour later, maybe you're sitting in a movie studio with your boss helping him close a $50 million movie." Most ultra-high-net-worth families have their staff sign extensive NDAs, and they have to have squeaky clean social media presences. "The stress can be more than even on Wall Street," Daniel says, recalling a time he took himself to the hospital while having a panic attack after a particularly stressful day as an assistant. For O'Hagan, one challenge of working in the homes of the elite is that professional and personal life often blur together. "You're not just working for a family, you're living alongside them, immersed in their rhythms, dynamics, and private moments," she says. She works across multiple international residences as one of eight nannies, but it can still be lonely. She's spent many holidays in the last few years — Christmases, Thanksgivings, her birthday, family celebrations — with whatever family she's working for. It's also not simple to break in and land roles in top households. Discretion and privacy are tantamount — most ultra-high-net-worth families have their staff sign extensive NDAs, and require their staff to have very clean presences on social media. That also means staffing agencies are often doing the headhunting on behalf of their wealthy clients. "It's a very cutthroat world," O'Hagan says, and the often the only way to even meet a family is to get represented by an agency. Once you get past that, private service quickly rewards excellence, says Daniel. He represented a Hollywood actor's personal driver who over 15 years became a personal assistant to the principle, then a executive assistant, and eventually was co-producing films with him and making "fabulous money." O'Hagan adds, "I dreamed of working for the world's most elite families at one point, and in just five years I reached that goal." She eventually wants to move on from nannying. She's in the early stages of starting her own agency and coaching business to help other young people break in, which she hopes will her the flexibility to start start her own family one day. "Peers of mine who are in corporate in New York City and young girls that I'm connected with have reached out to me so many times asking how I've gotten to where I am," she says. She recently encouraged her own younger brother to make the leap after a couple years working in media and public relations; he's now an assistant to a "celebrity esthetician" in Beverly Hills, she says. Edwards tells me she convinced her 25-year-old son to enter the field after he was laid off from a 9-5 administrative job. "I have worked in private staffing for a long time and I just said, look, if you are struggling in that office environment, go and see the world," she told me. Now he's a deckhand on a superyacht. This career, O'Hagan says, has "offered stability and meaning and a level of personal connection that I hadn't really found anywhere else yet." Emmalyse Brownstein was a reporter at Business Insider covering Wall Street culture and careers. She's now a full-time freelance writer and journalist.
