TOP 100 MAGAZINE

Skip Wilson

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Skip Wilson has built his career at the leading edge of change. A bestselling author, podcast host, and the founder and CEO of DRAFT Media Partners, he has spent more than two decades shaping how audiences consume content and how advertisers reach them. From the earliest experiments in streaming audio to today’s complex attribution models, he has been in the room when digital media reinvented itself, repeatedly. The throughline has always been the same: build systems that work in the real world and make growth predictable.

 

Skip’s unique vantage point was forged inside some of America’s most influential media organizations. At CNN, he served on the Special Projects team during the launch of iReport, one of the first large-scale user-generated content platforms. Later, as vice president of digital media at iHeartMedia, he helped bridge the gap between traditional radio and a new digital universe that didn’t yet have a name. The company was preparing to launch the iHeartRadio app and needed someone who could translate technology to sales and sell possibilities to advertisers. Skip became that bridge. Revenue for the division went from under $100,000 in its first year to more than $22 million when he left—proof of how dramatically consumer behavior was shifting and how quickly smart strategies could reshape an industry.

 

In 2020, after years of driving digital innovation inside large organizations, Skip launched DRAFT Media Partners in Greenville, South Carolina. Today the company plans, launches, and manages advertising campaigns across digital, traditional, and emerging channels, combining creative, media buying, and real-time reporting into a single execution engine. DRAFT manages several million in monthly ad spend, serves over 170 clients, and specializes in building high-efficiency infrastructures for small to mid-sized agencies and businesses that need scalable growth. The firm’s planning tools can forecast exactly how many leads or sales a campaign should generate, and their attribution systems track the only number that ultimately matters: customer acquisition cost.

 

The company’s growth is a direct reflection of Skip’s philosophy. First, solve a problem well. Second, be transparent. Clients and agency partners began referring him almost immediately, and the business expanded rapidly. DRAFT’s first year after shifting away from a software-only model was driven almost entirely by referrals. In the second year, momentum accelerated as past advertisers returned—many of them now representing 10 to 15% of the client base. The company has since earned multiple industry honors, including the 2024 Global Recognition Award for Advertising Solutions, and MarTech Awards for Best Marketing Software Company and Most Intuitive Software Design.

 

Decades of experience have shaped not only what Skip builds, but how he leads. He is still the primary communicator of the company’s mission, still speaking and writing, still advocating for clarity in a noisy industry. His work sits at the intersection of data, creativity, and execution—a place where results matter more than buzzwords.

 

Skip, what inspired you to start DRAFT Media Partners?

 

I had been inside large media organizations for a long time, and every time a new platform or format came along, we had to build the playbook for it. That experience taught me two things: emerging technology creates opportunity faster than companies can adapt, and most organizations struggle to execute consistently once the plan is in place. After years of watching the same patterns repeat, I wanted to build something that could operate with more agility and serve more people.

 

The spark for DRAFT was seeing how many businesses and agencies were trying to keep up with modern advertising, but they lacked the tools, the people, or the expertise to do it well. They didn’t need another dashboard or another software product—they needed execution. I knew the systems could be built, and I knew how to build them, so it became the natural next step. The goal was simple: make advertising more predictable and more accessible. DRAFT grew from that idea.

 

How valuable was your broad experience in shaping DRAFT’s model and services?

 

Incredibly valuable. Even though DRAFT is my first business, it didn’t feel like my first business. Inside those big companies, I had been basically starting from scratch multiple times. That experience helped us avoid mistakes and lean into the things that actually matter: what clients care about, what advertisers care about, what partners care about—and what they don’t. We originally launched as a software company. We had built a media planning and placement tool and planned to charge agencies to use it. But they didn’t have the people to place the ads. They needed an execution partner. Many of them already knew me as “the advertising guy” from my iHeart days, so after we built the plan, they’d ask, “Can you run this for us too?” That was the pivot that ended up becoming our business model.

 

Is that experience part of what makes DRAFT unique?

 

Yes. We look at every campaign through three stages: planning, execution, and attribution. Our planning tool gives clients a clear forecast of what success should look like—budget, platforms, expected results, and conversion targets—so everyone knows what we’re aiming for before anything launches. Then we have access to platforms most small agencies simply can’t afford, which lets us target more precisely and manage campaigns at scale. And finally, we measure what people actually care about: customer acquisition cost. Most agencies stop at clicks or cost per lead. We track how much it costs to generate real revenue, and that’s the metric that ultimately matters.

 

After building and scaling divisions for major organizations, what feels most rewarding today?

 

It’s seeing a local business or a small agency grow. They’re not glamorous. They don’t have big budgets. But when they scale, it matters. It changes lives. It creates jobs. It’s incredibly meaningful to play a role in that. Growth is fun, but impact is better.

 

 

Skip Wilson
CEO: DRAFT Media Partners
Website: https://draftmediapartners.com
LinkedIn: www.linkedin.com/in/skipwilson
Facebook: www.facebook.com/DRAFTAdTech
Instagram: www.instagram.com/draftadvertising