Meet a 27-year-old concierge at the Four Seasons hotel catering to VIP guests paying up to $25,000 a night

• I shadowed a concierge in charge of high-paying guests at the Four Seasons in downtown New York.
• I saw the different ways hotel employees cater to VIPs paying up to $25,000 a night.

Underneath the Four Seasons in downtown New York is a maze of hallways, hidden entrances, and secret elevators.

The underground network feels like an ant colony as security guards, doormen, and housekeepers labor away out of public view. The queen ant in this metaphor is 27-year-old guest relations manager Jessica Waddy, whose job revolves around the hotel's high-profile guests and their countless needs.

"It's like an unscripted reality show," Waddy said. "Behind the scenes, there's a whole village of people running around doing things you don't see."

Wearing a polka-dot dress and three-inch black heels, Waddy somehow manages to walk incredibly fast without looking rushed or frazzled. Her three cell phones constantly buzzed throughout the day — it's Fashion Week in New York and the hotel is booked to nearly 100% capacity.

She led me down to the cellar level and into a room where the hotel stores the belongings of regular guests, some of whom spend several months at the hotel each year. There's a tempur-pedic mattress topper, video game console, children's toys, and a consulting executive's entire wardrobe.

"He's very specific about how his closet is organized," Waddy explained.

Down the hall, there's a loading dock for celebrities and their drivers to dodge paparazzi and make a discreet entrance into the hotel. On Sunday, when the street was closed for a 9/11 memorial service, hotel security "finessed" police to let a celebrity guest drive through, Waddy said.

From there, VIPs enter one of four private elevators in the basement that lock once in motion, barring any common folk from hopping in on the journey up to their suite. Most celebrities are practically nocturnal during their stays, Waddy said, adding that nearby restaurants will stay open so they can eat dinner unbothered and alone at 1 a.m.

As we emerged from the basement, Waddy was called over to greet a high-profile guest checking in under an alias. The receptionist had never met him before, so Waddy is tasked with matching his face to the code name.

"We can't just be handing out room keys willy nilly," she said.

From procuring special toilet seats to washing bed sheets with a specific brand of detergent, the devil is in the details in this industry. Within two hours, I only hear one guest complaint: She was given a double room instead of a full. Her disappointment was quite clear.

"They pay more for one night than my rent," Waddy said. "So they deserve all the attention we can give them."

The needs of high-profile guests are listed on a "rider," a document that's typically multiple pages long and attached to their hospitality contract. But it's not the length of the list that creates a problem, Waddy said, it's the little notice with which staff receives them.

A VIP guest once requested all the furniture be removed from an extra room at 10 p.m. the night before check-in so they could convert the space into a giant wardrobe, Waddy said.

Another guest staying at the hotel's Empire Suite, which costs $25,000 a night, said he would only play Xbox on an 85-inch television — 10 inches smaller than the hotel's flat screens. The result was a wild goose chase through Staten Island and Queens to purchase two brand-new screens before his arrival.

"Our director had to get his car and go to two different stores so this guest could play his Xbox on the TV that he wanted," Waddy recalled. "We had to squish them into his car with one of our sales interns in the back."

With Monday officially kicking off Fashion Week, the hotel was swarmed with influencers and models. Upstairs, I watched a tall brunette dressed in head-to-toe neon pink feathers exit a celebratory brunch hosted by Vogue.

The hotel flew in three different bakers from across the country to assist with the brunch, one employee told me. Dozens of pastel cakes, gold-dusted cookies, and metallic blue cream puffs sat untouched after the brunch concluded. Waddy reassured me the leftovers would be transferred to the staff cafeteria.

"I told them we shouldn't give fashion people sweets," another staff member joked.

One of Waddy's three phones starts buzzing again, sending us back to the lobby downstairs. It's now around noon, so guests are starting to check out.

The hotel was short-staffed — a combination of jury duty, sickness, and labor market woes — so interns and security guards are handed lists of room numbers to knock on doors and politely persuade any lingerers to leave. With the hotel occupancy this high, there's very limited wiggle room for late check-out, Jessica explained, comparing check-in and check-out to a game of Tetris.

Everything goes smoothly until a wild card request threatens to set it all off-balance. A high-profile guest has called to request an observance of the room her recently-deceased mother last stayed in, but another VIP guest is scheduled to check-in soon. These are the types of conundrums that eventually make their way over to Waddy, who somehow is able to resolve them all.

"A concierge isn't just your basic making a reservation at Carbone, getting into Polo Bar, or scheduling hair and makeup appointments," she said. "We handle everything and anything. It's so unpredictable — I love it."

Do you work at a luxury hotel? Share your story by emailing this reporter at htowey@insider.com