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iHeartMedia’s Bob Pittman looked inside his own home for the 10th weekly episode of his podcast “Math & Magic: Stories from the Frontiers of Marketing,” talking shop with iHeart CMO Gayle Troberman. She explains to the CEO, “No matter what job I’ve had—and I’ve been on pretty much every side of the marketing table… client, agency, media company, creative—I’ve realized that you follow great people and you’ll find your way to adding some value. Somehow that kept pulling me back into content and marketing.”

Asked how she first decided to be in the marketing profession, Troberman tells Pittman, “I’m not sure I ever decided to be a marketer; I always refer to it as effective stumbling. I’ve followed passions and ideas and things that make sense without overthinking them. I’m not a big planner.”

“Bewitched” was her favorite show as a kid, and she eyed Darrin Stevens’ career in advertising. “Wow, these guys get paid to sit around and make up crazy ideas and then go pitch them to people,” she says. So, sure enough, her first significant career stop was working for a major ad agency. “I wanted to be a copyrighter, my ‘Bewitched’ vision of these great offices, sitting around with a cocktail and making up sentences.” Ultimately, she worked in the PR department, teaching her the importance of sound ideas.

Next came Microsoft, where she truly segued to marketing. “I was working with early internet properties. It was a fun giant playground of new and learning,” she says.

Troberman came to iHeartMedia when Pittman called upon her in the midst of the name change from Clear Channel to iHeart. “You said, I think I’m going to change the name of the company. I said, ‘That’s a little odd… iHeartMedia… and we wrestled through the pros and cons,” she recounts to Pittman. “Then you said something like, we’re going to do it and we’re going to do it in six weeks. Do you want to help?”

She adds that such a significant rebranding “felt impossible and yet when you broke it down, it was a series of what could have been a 100-page spreadsheet,” instead with a series of places where the brand appears… “So we did it, painted over it, changed it. The key learning for me was continuing to see the possibilities and continuing to fight even when you lose. It was the right idea.”

Today, coming from Microsoft, she is able to offer a balanced perspective of digital vs. traditional platforms. “In the digital era, we’ve all become so enamored of the new, next, shiny. I love being on the leading edge, trying things first. Part of why I got into marketing is to not do the same thing over and over, so testing in these new spaces and whatever the next flavor is, is important—but one of the lessons learned is the power of broadcast media.”

That has to do with recognizing the power of scale, Troberman says in the “Math & Magic” podcast. “That’s something I see with clients at iHeart over and over again, the power of radio to reach nine out of 10 Americans; it is not something to be overlooked. I think sometimes our human biases are really getting in the way to honestly balance math and magic. I say it to clients pretty much every day: You need to look at the math and decide which magic fits into that math.”

She adds that in this day and age, with so much media and so many brands competing for face time, “We need to have a voice with the consumer all the time, in real time, every day with a touch point with consumers. Finding the places where you can afford to do that and finding things worth saying every day… that is part of the magic of the marketing landscape.”