Stephani Estes began her career as a special education teacher and then pivoted to working in the media industry. Since making the switch more than fifteen years ago, she has worked in different facets of media planning, wearing many hats. The key to her success? Embracing challenges head-on, staying hungry for knowledge, and using the foundation she built as a teacher to guide her principles.
There are many paths toward a career in ad tech, and not all of these are linear. Proof of this is in Stephani Estes’ career journey from special education teacher to Chief Media Officer for Goodway Group. In between, Estes has gained valuable experience working in several media executive and management roles for companies like Cramer-Krasselt, McCann, and Starcom MediaVest Group. This year, we at AdMonsters are honored to announce Estes as a Keynote Speaker for the Sell Side Summit, held in Fort Lauderdale, Florida, March 9-11, 2025.
In line with the event’s theme – Cracking the Buyer’s Code – Estes’ keynote is titled “Think Like a Buyer: The ROI Roadmap for 2025.” This talk couldn’t come at a better time amidst recent changes in the industry, from privacy regulations to AI and buyer expectations.
We caught up with Estes to talk about her career journey and what keeps her invested and motivated to succeed.
These Media Roots Run Deep
Estes says she knew she was interested in media strategy as far back as fifth grade, when she took on the roles of newspaper editor and ad sales lead for a school project. She explains, “I loved the idea of sharing information and creating a message that stuck with people.” As a student at the University of Missouri, Estes studied journalism and enjoyed her classes on media in particular.
The strategies she learned during her college tenure focused on print, TV, OOH, and radio, formats that Estes says made it simpler to aggregate reach. The current landscape is fragmented, making it more difficult to grab consumers’ attention. However, on the plus side, more tools and data are at our disposal to achieve success. Ultimately, though, the overarching objectives in the industry haven’t strayed too far from the goals of Estes’ fifth-grade project.
“It’s a fun puzzle to tackle every day – and at the heart of it, media is still about sharing information and creating a connection that sticks,” she shares.
The Path Less Traveled Can Steer You Where You Belong
Estes’ career path did not follow a linear trajectory, even with the self-awareness that she was interested in media at such a young age. She began her career journey straight out of college with Teach for America, working for two years as a high school special education teacher in St. Louis. While she acknowledges that the two careers may not seem aligned on paper, Estes asserts that special education teachers use many skills that are applicable in media.
For example, she explains, “I needed to learn to think on my feet, problem-solve with limited resources, and communicate information in various ways to meet student needs.”
Though she greatly enjoyed teaching, the media industry called to Estes, and after two years, she left to pursue a position as a print planner/buyer for Starcom. This position led to a move to strategic planning, and it’s in planning that Estes has made a home for herself in the industry.
She credits her penchant for raising her hand to take on challenges as a reason for the way her career has progressed. “Challenges are how I’ve grown my career! I enjoy a challenge, whether it’s figuring out how to set up an effective team or navigating a business challenge with a client,” she notes. A few notable challenges Estes has faced head-on include working with print publishers to package Crayola’s print and digital assets together (unheard of at the time), building Disney Parks’ first mobile video plan the year after the iPhone’s launch, and partnering with the creative team at Bernstein-Rein to launch an early-days hashtag campaign to relaunch Hostess Brands.
Estes spent almost eight years at Cramer-Krasselt wearing many hats, including VP of Digital Strategy, SVP Director of Media, and General Manager of the Chicago office.
“With each role, there was a lot I didn’t know, which gave me a huge opportunity to learn. I love to learn and build, which is what ended up bringing me to Goodway Group. We’re building something really exciting here, and that’s a new challenge for me to figure out,” she shares.
Checking Privilege: DEI Is Not a Dirty Word
Estes has cemented herself as a valuable asset in the media world, but the lessons she learned as a teacher are still present. Teaching built a sturdy foundation of principles and illuminated techniques to apply to the ad tech industry. It also showed Estes the power of bringing diverse voices to the table.
“When you’re teaching special education, you have to tailor your lesson to meet the needs of different types of learners.” Teachers need to consider the variations in learning styles when they are relaying new material; similarly, marketers are most effective when they factor the audience into their approach.
Estes shares about her time at Teach for America: “Being a part of Teach for America was a gift for me. It opened my eyes to our country’s social and economic realities that continue to persist (and, in some instances, are being exacerbated). It highlighted for me the privilege that I hold and reminds me that I need to use that privilege to support those who don’t have as much.”
She strives to include diverse voices at the table because she believes keeping underrepresented groups in mind strengthens the end product. “As Cindy Gallop wisely says, ‘DEI stands for Drive Excessive Income,’ and I believe that wholeheartedly,” Estes asserts.
Learning Is a Lifelong Journey, but Some Skills Are Ingrained
For those looking to get started in ad tech, Estes advises that almost any part of the industry itself can be taught. However, to truly succeed, you will need inherent skills that can’t be learned, such as critical thinking and curiosity, which are key. A keen desire for knowledge and a willingness to ask questions are also essential.
“Explore other viewpoints. Be open and non-judgmental with yourself and with others. I think this becomes increasingly important as we start to lean on things like GenAI to work. You need to be curious about how AI can help you with your work and have strong critical thinking skills to evaluate what you get from AI,” she advises.
The audience will get an opportunity to learn from Estes firsthand during her keynote speech at the Sell Side Summit. We asked for a teaser of what attendees can look forward to, and Estes shared, “As someone who is an avid content consumer, a journalism enthusiast, and a media fan in general, I want publishers and the open web to be successful. I want to share a few ways we’re evolving how we approach buying at Goodway Group and how publishers can successfully partner with buyers for more revenue.”
Want to hear more from Estes? Join us next month at Sell Side Summit in beautiful Fort Lauderdale to hear more!