HEAD COACH


April 26, 2023

One of America’s top executive coaches emerges from behind the curtain.

story by Robert Cocuzzo

photography by Kit Noble

Jeannie Esti is an executive coach of the highest order. Some of the most powerful CEOs in America have her on speed dial. In times of crisis, her clients have been known to charter private jets just to speak with her in person. Armed with cunning business instincts and a megawatt personality, this longtime Nantucket summer resident has spent decades helping leaders lead through her trademark no-nonsense approach. Today, her waitlist rivals that of the Steamship Authority. Locked up in NDAs, Jeannie’s role in facilitating corporate conquests has been entirely hidden from the public eye. But more recently, rumor has it that Jeannie’s story has grabbed the attention of top producers in Hollywood who are interested in bringing her out from behind the curtain and into a leading creative role.


Jeannie’s energy fills every room she enters. It radiates off her like a forcefield that you can feel even over the phone. She’s funny, quick-witted and refreshingly irreverent. Her inexhaustible sense of humor is matched with a steely-eyed clarity for business that helps her dice highly complex situations down to size. It’s what has made her an indispensable ally to Fortune 500 CEOs, unicorn entrepreneurs, professional sports power brokers, lifestyle influencers and A-list celebrities.


“There’s a moment in The Wizard of Oz when the good witch says to Dorothy, ‘You had the power all along,’ and that is what I remind my clients of,” says Jeannie. “I am not here to shift and change your life. I’m here to show you where you can shift and change your life. You want a business that hums? You want to grow your business? You want to create revenue? I’m here to work with you shoulder to shoulder—I am the navigator—but I’m not driving. You’re doing the work.”


Jeannie was born with business in her blood. The daughter of a direct-marketing CEO, she spent her formative years stuffing envelopes after school for a penny a piece. When her friends went off to get summer jobs scooping ice cream or life guarding, Jeannie was working on the divestiture of AT&T in New Jersey. “I was wearing stockings on my legs while everyone else was running around in flip-flops,” she says with a laugh.

Her business background served her well. After graduating from St. Bonaventure University and while earning a master’s from Fordham, Jeannie hit the fast track and quickly climbed the ranks of American Express Publishing and then Bank of America. “I was really fortunate to have had that early career experience as I was told it gave me a slight edge over other candidates who were also new college graduates,” she says. “I had done essentially three internships by the time I graduated so I walked into a position with more business experience than many new grads. So the trajectory of my career was faster...and I had a lot of responsibility at a young age.”


But over time, Jeannie “got tired of leading the deals, making big profits for other people and not sharing enough in the return,” as she put it. One night while her father and uncle, who was the CEO of Bank of New York, were puffing cigars and sipping over-priced port, they challenged her to start her own strategic marketing firm. After Jeannie hung her shingle, her business took off. In short order she came to represent big-name clients in the NFL, The Nature Conservancy and National Geographic. Life was good. She earned a princely living, traveled the world and established herself in Washington, D.C.

Then in 2002, a CEO invited her to attend a leadership conference being held at Harvard. After the first day of listening and interacting with keynote speakers Jack Welch and Rudy Giuliani, Jeannie returned to the conference on the second day where a professional coach was presenting. Something about this kind of leadership facilitation clicked with Jeannie—and the coach herself recognized that. Before the day was out, she cornered Jeannie and said, “You not becoming a coach would be like Picasso having decided not to paint.”


Jeannie was intrigued by this compliment. It stuck in the back of her mind for six years until she decided to enroll in a coaching certification program, more out of curiosity than any serious intention of pursuing it as a career. While most of the attendees were wearing casual clothes on a Friday afternoon, Jeannie, who had to return to her office afterwards, strut into that coaching certification program carrying two phones and wearing a Hillary Clinton-style pantsuit. Within two hours of sitting down for the program, she knew in her bones that she had just found her calling.


“It wasn’t a good feeling,” she recalls. At the age of forty-two and at the top of her career, was she really going to give up her lucrative business to become a coach, a profession she knew virtually nothing about? “One thing was for certain, my value and differentiator would be to stay on the business advisory side of the narrative and blend in coaching when necessary,” she says. “I didn’t want to abort all of the business acumen about running a P&L to all of a sudden start talking to clients about the weather in their souls. It was then, and still is important to me, that a client sees a return—however they define it.”

Indeed, the idea of becoming an executive coach had a magnetic pull on Jeannie. It felt like something she had been unknowingly training for since those days of stuffing envelopes for her father after school. Coaching would not only call upon her business background but also her personality. Jeannie decided to take the leap. She sold her house in D.C., put most of her belongings in storage, and moved to Nantucket where she intended on giving coaching a shot. She spent the next two years building her business and hasn’t looked back since. Today her roster of clients numbers in the dozens and she has at least five other coaches working for her.


“I was initially skeptical of coaching, then a good friend mentioned how impactful Jeannie was to his career,” says Craig Descalzi, the CEO and founder of Morrison Avenue Capital Partners. After conferring with other CEOs who had utilized a coach, Craig enlisted Jeannie’s services. “Despite her youthful appearance and demeanor, Jeannie has tremendous experience, both from coaching and her own career,” he says. “If she takes you on, you can count on her first advocating for you, and then solving problems.” Craig describes Jeannie’s coaching approach as aggressively supportive. “Coaching, or should I say receiving coaching, can be a difficult and dare I say humbling process,” he says. “Jeannie differentiates herself through her passion and personality... she finds a way to make her immense impact fun.”


Through some twists of fate, Jeannie’s story has garnered the attention of Hollywood elite who are taken by her character as a high-powered female CEO soothsayer. “I have been very fortunate to be working with some incredible producers and writers who have been interested in creating a storyline potentially based on what I do and how I do it,” she says. “But theirs is a world that requires creativity, patience, timing with a twist of the miraculous so I’m not quitting my day job.” Time will tell whether Jeannie Esti will make her big-screen debut, but for now she’s content to continue to play a supporting role alongside some of the biggest performers in the business world.

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