Rachel Charlupski
Babysitting guru Rachel Charlupski at Maurice Gibb Memorial Park on South Beach.

It’s 12:15 am and Rachel Charlupski is fielding a very important call from the Continuum. “[A client] wanted a babysitter at 12:30 am,” Charlupski explains. “I love my clients, and I don’t like to say no.” So 15 minutes later, a sitter arrived.

That 24/7 availability, anticipation, and ability to impeccably match sitters to clients have created a national empire of sorts for the 29-year-old Charlupski, the founder and CEO of Miami-based The Babysitting Company.

Five years ago this month, Charlupski moved her business to Miami after establishing a hold on the Phoenix market. Now, she operates a network of 1,200 sitters across 10 major markets, including Miami, Los Angeles, Chicago, New York, and London. But with 600 sitters and counting in South Florida, her hub remains the busiest. “I have clients that come for a week, and they end up staying the entire season,” she says. “They don’t want to leave.”

Miami’s transient and seasonal nature proves good for business, and for that reason, many sitters have been with Charlupski for years. “When one client uses a babysitter for Christmas, the next Christmas they come in and they want her, and they’re in town with two friends, and they want two more babysitters,” Charlupski explains.

To help manage the babysitting boom, Charlupski has hired her own help, but stays true to her business acumen, which she attributes to her entrepreneurial father. “The relationship is so much more important than the dollar,” she says. “My number-one priority is making sure my clients are happy, my babysitters are happy, and anything after that is really a bonus.”

Client loyalty also stems from Charlupski’s ironclad hiring process that yields foolproof professionalism, safety, and, of course, child-friendly sitters. Sitters undergo a rigorous screening process that includes full FBI background checks and 25 hours of training, CPR certification, and shadowing. When clients make a request, they are required to complete extensive questionnaires on each child to perfectly match sitters and families based on shared interests—sitters range from ballet dancers to retired teachers—and personality traits.

If this seems intense, there’s good reason. The Babysitting Company’s sitters are qualified to do much more than just read a bedtime story. “I’ve had a sitter go to a job at Canyon Ranch that was supposed to be during the day,” Charlupski recalls. “She was just going on a boat trip to Fisher Island and back. She called and said, ‘I was sent home to pack my bags. We’re going to Montreal and then we’re going to Aspen and then the south of France for two weeks.’” She shipped out the next morning. “That happens often.”

Considering the lifestyles of the company’s jet-setting, high-profile clients, this type of availability is a must, as are multilingual capabilities, discretion, and confidentiality. Charlupski’s client list of up to 2,000 reads like a roster of the world’s who’s who, including supermodels, royalty, high-level executives, celebrities, and professional athletes. The company also works with hotel partners like the Biltmore, the W South Beach, The Setai, and The Four Seasons.

As Charlupski handles her high season—during the holidays, babysitters can work three jobs a day and have been booked months in advance—she has her eye on expanding to Las Vegas and Dallas. But her heart—and hub—will remain here. “Everybody comes to Miami,” she says. “I love Miami.”

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