IT’S 9:00 am sharp when Natalee Prout appears on Zoom, already at her site office and squeezing in this interview before heading back out into the thick of her day. She’s calm but alert, the kind of calm that comes from someone well-acquainted with the fast pace and high stakes of her job.

That day? Packed. After the interview, she’s heading straight back into a patchwork of meetings, site walk-throughs, permit inspections, procurement planning, and conversations with everyone from architects to environmental consultants. It’s all in a day’s work when you’re managing the development of The Pinnacle — and not just any development, but a project that’s rewriting the rules of luxury real estate in the Caribbean.

At 29, Prout is helping to steer one of the largest real estate builds in Jamaica’s history: a US$450-million landmark development that will house the first Accor/Ennismore branded hotel and residences in Jamaica. Spanning 17 acres on Reading Peninsula in Montego Bay, The Pinnacle isn’t just ambitious, it’s historic. When complete, it will stand as the tallest building in Jamaica and the entire Caribbean.

“One minute I’m climbing a 16-storey tower, the next I’m checking our mangrove nursery to make sure we’re abiding by permit conditions,” she says. “I like it that way. I’m not a fan of doing the same thing every day.”

An unconventional path to project leadership

Prout is not what you’d call a conventional project manager, and that’s part of her edge. She never planned for this career path. In fact, she studied marketing management and was set on a very different trajectory.

“I was literally just talking to friends about marketing when someone invited me to a site visit,” she recalls. “But I went, and it piqued my interest. It was unfamiliar, but exciting.”

What she saw was potential and creativity. “Marketing and project management are closer than people think,” she explains. “Both are about taking an idea and bringing it to life.”

The transition proved more relevant than she initially realised. Managing a branded residence project like The Pinnacle requires understanding not just construction logistics, but the hospitality brand experience that residents will expect. When units participate in Accor’s hotel rental programme, every residential detail must meet the standards guests would expect from a five-star hotel.

She credits several marketing skills as invaluable in her transition: “The ability to communicate clearly and persuasively — whether it’s presenting to stakeholders, managing teams, or negotiating timelines — has made a huge difference. Marketing taught me to think strategically, focus on the end user and manage multiple moving parts under pressure.”

After gaining experience on smaller projects, she knew she had to be part of The Pinnacle. The opportunity to work on Jamaica’s first branded residence project, introducing a concept where luxury residential living meets world-class hospitality management, was too compelling to pass up.

Building credibility in a new field

Making the leap wasn’t easy, and building credibility in a field she didn’t formally study came with challenges. “I did the work and let the results speak for themselves,” she says. “I asked smart questions, stayed curious, leaned heavily on research and over-prepared for every meeting.”

To those intimidated by not having the “right” educational credentials, Prout offers this: “Your degree is only one part of your story. What you do with what you have often matters more. Passion, discipline, and initiative can fill many gaps. The industry respects results, and those come from competence, not just credentials.”

One of her most humbling learning curve moments? “My first large-scale technical meeting,” she says. “It was packed with engineering jargon. I felt out of my depth. But instead of retreating, I took notes, followed up with questions, and spent the next few weeks immersing myself in the technical side.“

This adaptability proved crucial when working on a branded residence project. She also learnt a crucial leadership lesson: don’t try to do it all alone. “Early on, my biggest mistake was trying to do everything myself. I thought asking for help showed weakness,” she says. “But I learnt that delegation and collaboration are strengths, not flaws.”

Managing history in the making

Now, she finds herself at the helm of a project that’s breaking new ground in multiple ways. Beyond being the Caribbean’s tallest building, The Pinnacle represents Jamaica’s entry into the luxury branded residence market — a concept where residents enjoy hotel-level service standards, professional hospitality management, and the prestige of association with established international brands.

“It’s history in the making,” she says. “When my family visits the site, especially my son, and sees what I’m doing, he’s like, ‘Wow…you’re actually a part of building this?’ That moment of pride, it’s everything.”

But with ambition comes pressure. The project’s timeline is aggressive, and every day involves coordinating with multiple stakeholders: from ensuring the luxury units meet Accor/Ennismore’s exacting standards, to managing the environmental requirements of building in a marine reserve, to overseeing amenities that rival the world’s best resorts.

“Natalee has this rare ability to see both the big picture and the smallest details,” notes a senior colleague who has worked closely with her on The Pinnacle. “She can be discussing environmental compliance in the morning and luxury finishes in the afternoon, and she brings the same level of focus to both. It’s exactly what you need for a project of this complexity.”

Her leadership philosophy is rooted in clarity and trust. “Value the details, trust your team, and stay professional,” she says. “What I value most in my team is efficiency and professionalism. Just knowing I can rely on them.”

Defining success and legacy

And what does success look like to someone balancing massive expectations and personal values? “Success, for me, is about sustainability and alignment. It’s about achieving big wins without losing myself in the process,” she says.

As for The Pinnacle’s legacy, Prout doesn’t hesitate. “I want it to be more than a luxury address; I want it to symbolise progress and opportunity, something that enhances the global perception of Jamaica as a premium destination.”

Advice for aspiring project managers

Her advice for getting started? “First, get project exposure. Volunteer or assist on any project-related tasks in your current role. Second, upskill strategically — take a project management course or certification. And third, find a mentor, someone already in the field who can give insight and guidance.”

For Natalee Prout, saying yes to new opportunities, even intimidating ones, has been a game-changer. “Almost every pivotal moment in my career started with a ‘yes’ I wasn’t fully ready for,” she says. “Growth happens when you’re stretched. It’s uncomfortable, but it’s necessary.”

Then she’s off again, another walk-through, another decision, another detail that will someday rise into the skyline — and help establish Jamaica as a new player in the luxury branded residence market that’s reshaping Caribbean real estate.

Natalee Prout, assistant project manager at The Pinnacle.