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Gayle Troberman

President & CMO of iHeartMedia; Former Chief Creative Officer at Microsoft; LGBTQ+ Leader

Gayle Troberman is a creative force like few others, having built brands that include Windows and Office–-pioneering everything that we now understand to be digital marketing before that was a “thing.” 

She knows how to see around corners, build entirely new businesses, sell the vision, create new realities, and “stumble intentionally” toward success in all aspects of life.

Gayle built many of the first successful online brands, the first email marketing capabilities, the first in-game advertising, and the first branded content practice on the internet in her 16 years at Microsoft, where she eventually served as Microsoft’s first-ever Chief Creative Officer.   

She understands how to develop bold, transformative marketing platforms. And she is equally adept at creating evangelists and nurturing ideas so they can find their way through organizations and make it into the world–-uncompromised–-to deliver maximum and measurable impact. 

As CMO of iHeartMedia, Gayle has been the single biggest evangelist in fueling the audio revolution in marketing, as consumers spend 30% of their time listening and marketers spend less than 10% of their media dollars on audio advertising.


Gayle has exposed this gap, and developed an incredibly robust and enduring Power of Sound presentation platform that has served as a wake-up call for the advertising world.  

She has delivered this rallying cry to audiences at hundreds of major conferences, agencies of all sizes, and brand events, including CES, AdvertisingWeek, Silicon Slopes, Ad Age, SxSW, Cannes Lions, Summit Series, Brand Innovators, 4A’s, Female Quotient, and more.


She has been joined on-stage by an array of talented audio gurus, including Ryan Seacrest, Charlamagne tha God of “The Breakfast Club,” Questlove, Halsey, Sam Smith, Melissa Etheridge, and many others. 

Gayle is a lesbian and proud member of the LGBTQ+ community, and has been out–open and proudly paving the way for talented, diverse professionals to get heard, get hired, and get to the top–since the early 90’s.   

She is an outspoken and unapologetic voice in media, marketing, and business who has the unique ability to inspire, educate and challenge teams, organizations, and individuals in ways that surprise, provoke, and provide actionable roadmaps for transformative thinking.

Her array of real world access, experience, and opportunities have yielded an unmatched stockpile of lessons-learned and shortcuts to help anyone and everyone find their inner marketer.  

Simply put, Gayle Troberman is one of the most inspiring, authentic and original speakers of our time.

Awards Include: Clios, Cannes Lions, Webbys, Effies, Silver Anvils and more.

Gayle Troberman Headshot.jpg

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Let's Get Ready to Stumble

Tap into your instincts, not just your intellect.


Join Gayle for a presentation that is all about you, and how to unlock your ability to "unplan," see and seize the moments, the people, and the possibilities that will present themselves if you can learn how to tap into your instincts and not just your intellect.  


The best plans are still just a guess as to what might work. The best results and the game-changing and career-defining moments usually happen in the most unexpected situations.  


Learn how to seize those moments and stumble away from the expected toward the exceptional as Gayle shares years of experience, anecdotes, and practical insight based on her work with some of the biggest brands in the world



The best business schools don’t prepare us for the modern workplace, where understanding the art of we, as opposed to me, can make all the difference.  


But it’s not about making friends or creating "Kumbaya moments." 


Rather, it’s about how to teach and inspire others, because our collective success is the only success. 


Yet, most organizations ignore this critical premise.  


In this customizable presentation, Gayle shares how she learned early-on (from her spouse, who is a teacher) that even the toughest marketing presentation to the least-interested team or client is still a lot easier than getting a room full of students to care about history. 

Muppelucky: Where Hard Work Meets Opportunity

It’s a rare and special power to admit the role that "luck" plays in our success. 


But can we control how lucky we are?

Gayle believes that we can, and she calls it "Muppelucky."


In this popular presentation, Gayle teaches audiences how to channel all the goodness in our lives, all those lucky breaks and happy accidents, to tap-into the special powers we all possess to forge our own paths and define our own success, on whatever terms we desire. 

Because, It's Everybody's Business


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