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Features | Jun. 2025

ON BRAND

By Joe Rosenthal

PHOTOGRAPHY BY MAGGIE RIFE
STYLING BY THERESA DEMARIA
HAIR & MAKEUP LEANNA ERNEST

Advertising icon Cheryl Berman wearing Lela Rose, Neiman Marcus Northbrook

108 Main Cheryl Berman Wearing Lela Rose, Neiman Marcus Northbrook 2

After making advertising history as the Chairman and Chief Creative Officer of Leo Burnett, Cheryl Berman founded her own branding agency dedicated to big ideas and new beginnings.

108 H6a8334
Berman’s Wake Up Call at Cannes: Women make 88 percent of all purchases.
108 H6a8327
The Wall Street Journal’s “The Determined Ms. Berman”
108 The Journal Introduces Artist In Residence. Berman's Way To Connect Bands With Burnett Clients
The Journal introduces “Artist in Residence.” Berman’s way to
connect bands with Burnett clients

Back in the early aughts, The Wall Street Journal dubbed Chicago native Cheryl Berman “The Determined Ms. Berman,” running a full-page ad to recognize her stratospheric success in the advertising world—she had become the first woman to ascend to the roles of chairman and chief creative officer of Leo Burnett USA and the first woman to serve on the agency’s board of directors. It was a flattering and catchy nickname, but it paid a subtle disservice to Berman, whose determination is matched by her creative firepower, leadership ability, social insight, and knack for creating communications that resonate across generations. Her story doesn’t fit neatly into the magazine format; in fact, there’s a book forthcoming. But merely touching on the highlights should inspire anyone seeking to make their mark in branding, advertising, music, or business. Or, frankly, for anyone looking to make a mark in life.

After graduating from the University of Illinois at Urbana-Champaign, Berman spent three weeks working in journalism for her uncle before he fired her and told her to find another line of work. “If you wanna make things up,” he said, “don’t do it in my paper. You should be in advertising.”

With those fateful words, she followed the guidance of another relative who introduced her to an opportunity at Leo Burnett. She showed up for her interview and was asked for her “book.” Without skipping a beat, she replied, “Yeah, I’m reading The Other Side of Midnight.” The interviewer politely explained that a “book” was a portfolio, and she needed to have one to work at an agency. Armed with a weekend and a hazy concept of what a portfolio was, Berman returned the following week with her book, talked her way into a second interview, and the rest is advertising history.

She soon found herself part of the team that landed the agency-defining McDonald’s account, which put her on a fast track to advertising immortality, and found herself a mentor in Paul Schrage, the fast-food giant’s chief marketing officer. “People don’t raise the bar unless somebody makes you do that,” she says. “So that’s what I learned from him. He would say, ‘Hey, this is good, but maybe it could be better.’ He was there when Ray Kroc was around, and he’s still a friend. He was probably the best mentor I ever had.”

All the mentoring and on-the-job lessons clearly took hold, as Berman moved up the ranks and became the youngest copy supervisor and vice president in Leo Burnett’s history.

108 Berman Was Named A Partner In The Opening Of The Disney Institute In 1996
Berman was named a partner in the opening of the Disney Institute in 1996.
108 Cheryl Berman In Her Third Floor Office With Multiple Awards
Berman in her office
108 Berman's Mobius Awards For Excellence In Television Advertising
Berman’s Mobius Awards for excellence in television advertising.

As a copywriter, she wrote award-wining ads for United, McDonald’s, Disney, Hallmark, and 7UP. She won the first advertising award the Leo Burnett agency ever received (for a Nestlé Crunch commercial), Chicago Ad Woman of the Year, the Missouri Honor Medal for Distinguished Service in journalism, Ad Age’s 100 Most Influential Women, and Adweek’s 11 Most Inspiring Women.

In her spare time, she wrote songs that were performed at the Super Bowl halftime show and are still heard at Disney theme parks around the world, founded Miss Understood at Cannes, and launched Women on the Rise at Rise Interactive Ad Agency.

Berman’s pride in her career achievements is clear (her home office in Wilmette features furniture, framed art, and trophies from her last office at Leo Burnett), but she’s always mindful of what made her successes possible—the ability to forge a human connection. “I am all about making emotional connections that touch people’s hearts and minds,” she says. “You can’t feel or touch a brand, but it must touch you and make you feel something. A brand is first and foremost a promise. And if you keep true to your promise, loyalty grows. And if you don’t, it erodes, then people look for something else.”

It’s that belief in the power of brand that Berman channeled into the company she founded after leaving Burnett in 2008. A low-overhead creative company, unbundled specializes in high-quality strategic and creative expertise. The company has successfully shaped brands including American Greetings, Sky

Zone, SKATIE, the Joffrey Ballet, Start Early, and Pharmacyclics. At the core of the agency’s process is a unique branding workshop that Berman leads at her beachside home, allowing the environment to soak into the creative process.

As much as Berman is a traditionalist when it comes to branding, she’s energized to find herself in the midst of an industry being turned upside down by AI. She’s part of the world’s first AI advertising agency, Ad Legends, which has a mission to pair brilliant technology with legendary human talent to create world-class work. Clients can interact with AI trained by ad business icons, and if clients wish to collaborate live with a real legend, that will be possible, too.

“I’m hoping to help humanize AI,” she says. Coming from someone who broke through the boys’ club of advertising to rise to the very top, penned songs sung by Christina Aguilera and Gloria Estefan, and challenged the status quo for decades, it’s not difficult to believe she’ll do just that.

On the topic of future plans, in the early 2000s, the Wall Street Journal hired her to review a few seasons of Mad Men and encouraged her to write her life story. After doing several rewrites over the years, she’s planning to get the book published this year.

The book will be a testament to Berman’s energy, passion, and wisdom—all of which are contagious. It’s no accident that Berman followed so effectively in Burnett’s footsteps, only to step off the beaten path, making a beeline to her own brand of success.

108 Berman Received The Cannes Advertising Festival Gold Lion For A Mcdonald's Commercial
Berman received the Cannes Advertising Festival Gold Lion for a McDonald’s commercial.
108 Leo Burnett As Adweek's Cover Story

For more information about unbundled, visit unbundledcreative.com. For more information about Ad Legends, visit adlegends.ai.

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