In partnership with
Meet Kyle Whittingham.
Kyle is the Founder and CEO of Whittingham Sports, a rapidly growing sports marketing agency that has quickly established itself as a leader in emerging leagues within sports. He’s a rising voice in sports marketing, known for building audiences, scaling brands, and dominating on social media, but what makes Kyle’s story so compelling isn’t just where he has ended up - it’s that none of this was the plan.
Kyle didn’t arrive at Penn State dreaming of a career in sports. Like many students, he chose a major that felt safe. Supply chain management was booming. It promised stability, opportunity, and a clear path forward. He followed it all the way into a supply chain internship, where he quickly learned something important.
This wasn’t for him.
The work wasn’t bad, but the fit wasn’t there. Some might have viewed this as a waste of a summer, but for Kyle, taking that internship and learning what he didn’t want was exactly what was needed to set up his next move.
Shortly after finishing the internship, he switched his major to marketing and met a group of students building a drone startup. They didn’t have a marketing function – not even yet thinking about content, audience, or growth. Kyle stepped in, unpaid, but acting as the student-led startup’s “CMO,” and got to work.
There wasn’t a team to manage, so Kyle was doing everything. Posting content. Learning platforms in real time. Experimenting. Breaking things. Fixing them. The role didn’t come with a salary, but it came with something far more valuable: reps and real experience.
Kyle’s Career Path
That experience led him to the Drone Racing League Kyle first joined DRL as a Marketing Intern, working remotely while finishing school. What started as an internship quickly turned into something much bigger.
Over the next two years, Kyle progressed from Marketing Intern to Marketing Associate (his first full time role after college), and then to Senior Associate, Social Media & Fan Growth. Each step came with more ownership. He wasn’t just executing tasks. He was shaping strategy, running social channels, managing millions of dollars in paid media, supporting partner activations, and owning how the league showed up digitally.
DRL’s lean structure created space to move fast. Kyle took on responsibility early, learned in real time, and was trusted to operate at a level well beyond his title. Along the way, he worked closely with experienced leaders, including former NBA executives, who challenged him, mentored him, and gave him exposure to how high-performing sports executives operate.
The results followed. DRL became one of the fastest-growing sports properties on social, growing their TikTok account by over five million followers - more than Formula 1, NHL, MLS, PGA and NASCAR at the time. The audience Kyle and his team built generated $100M+ in sponsorship revenue and helped the company sell for $250M. During his time with the league, they were recognized with an SBJ award for Best in Sports Social Media and shortlisted for Hashtag Sports “Best in TikTok. When it was all said and done, Kyle had generated over 500 million video views across the leagues social channels.
His time there was a massive success, but after years focused on emerging sports, Kyle wanted to see the other side of the spectrum.
That curiosity led him to the NBA, where he joined Team Marketing & Business Operations, an internal consulting group that works directly with teams across the NBA, WNBA, G League, and beyond. His role sat at the intersection of data, strategy, and execution. The team analyzed what was working across the league, identified best practices, and helped franchises improve their business operations.
For Kyle, it was a crash course in scale.
Where emerging leagues required scrappiness, the NBA showed him polish. Structure. Process. What the finished product looks like after decades of iteration. The experience rounded out his background and gave him a reference point he didn’t have before.
Then the phone rang.
What Is an Emerging Sports Property?
An emerging sports property is a league, team, or organization that is still in the early stages of building its audience, commercial engine, and cultural relevance. These properties typically operate outside the traditional major leagues and are defined by smaller teams, leaner budgets, and less established infrastructure. Rather than maintaining legacy systems, they are focused on growth, experimentation, and proving their place in the sports landscape.
Because of that, roles inside emerging properties tend to be fluid. Employees are often asked to wear multiple hats, take on responsibility quickly, and operate with fewer guardrails. The pace is fast and the learning curve is steep, but the tradeoff is exposure and ownership. For professionals willing to embrace uncertainty, these environments can accelerate development by offering hands-on experience, visibility into decision-making, and opportunities to shape a business in real time.
Kyle was recruited to SailGP, leaving the NBA to join a global sports property at a moment of rapid growth. What followed was one of the most formative chapters of his career. He traveled the world with the team. Took on real ownership. Built marketing and content strategies from the ground up. Eventually, he was named Vice President of Marketing & Content for the U.S. SailGP Team, taking on leadership responsibilities at an age when most people are still learning how to navigate their first few roles.
Through his role he designed a one-of-a-kind helmet with Red Bull, rebranded the U.S. SailGP Team, highlighted by the ‘LIBERTY MARINE’ F50 Livery, and launched a global merch line with Tommy Hilfiger.
Along the way, the industry took notice. Kyle was named to the Front Office Sports Rising 25 in 2023, recognizing his impact and trajectory across sports business.
Through SailGP, Kyle developed a close relationship with Harvey Schiller, one of the most accomplished executives in sports history. Harvey became a mentor, a sounding board, and eventually, a catalyst. In conversations about career direction, growth, and timing, one idea kept surfacing.
It might be time to build something of his own.
Backed by Harvey, Kyle made the leap.
In April 2025, he founded Whittingham Sports, an agency focused on helping emerging sports properties, teams, and athletes grow their audiences and brands (check out this write-up from SBJ). The work draws directly from every chapter of his career: the scrappiness of startups, the scale of major leagues, and the trust built through relationships over time.
Kyle’s path isn’t about chasing titles or picking the “right” lane early. It’s about momentum. About trying things, learning quickly, and not being afraid to move on when something doesn’t fit. About taking responsibility when it’s offered and earning more through the work.
Work hard. Fail fast. And do it all with a smile on your face.
It’s working for Kyle.
Q&A: Landing a job in Sports Marketing with Kyle Whittingham
Q. You took on significant responsibility very early in your career. What did you do, intentionally or unintentionally, to earn trust so quickly from senior leadership?
A. I raised my hand whenever new projects came up and consistently looked for ways to contribute beyond my core responsibilities. I treated my “9–5” as the baseline, and used mornings and evenings to help wherever I could add value. Over time, I shortened the trust horizon by delivering consistently across different parts of the business, which allowed leadership to see reliability, judgment, and follow-through early on.
Q. You’ve talked about your preference for “failing fast.” What does that philosophy look like in practice, and how has embracing failure early helped you progress more quickly and make better decisions over time?
A. My career has been built in social media, where you can move fast, publish, and learn in real time. Failing fast, in practice, means increasing the volume of decisions and reps so you shorten the learning curve. At the Drone Racing League, we posted 5+ times a day on TikTok while others were posting once. That allowed us to learn in a day what others learned in a week, and get months ahead very quickly. I’ve found this applies broadly: progress comes from more at-bats. When you increase reps, you improve decision-making faster and build real experience, not just time on a résumé.
Q. As you continue to build Whittingham Sports, what traits or behaviors will you prioritize in your first 10 hires? For students and early-career professionals, how can those traits be developed before they ever land their first full-time role?
A. As I build Whittingham Sports, I’m prioritizing people who aren’t afraid to get their hands dirty and bring a positive, team-first attitude. This is a client-facing business, so being someone others enjoy working with really matters. I also value people who have challenged themselves before—doing hard things on purpose builds resilience and perspective. Above all, I look for curiosity: people who ask good questions, learn quickly, and constantly want to get better.
For students and early-career professionals, those traits can be developed long before a full-time role by seeking out responsibility, saying yes to uncomfortable opportunities, and treating every project like it matters. That mindset compounds fast.
On that note, I’m currently looking to bring on six social media management interns. If you’re interested, shoot me a message on LinkedIn.
Key Takeaways
1. You don’t need a perfect plan to start.
Careers in sports are rarely linear. The people who make progress aren’t the ones with everything mapped out. They’re the ones willing to start, learn quickly, and adjust as they go.
2. Prioritize ownership and the titles will come.
Early growth comes from taking responsibility, not chasing labels. If you consistently own problems, deliver results, and make yourself useful, the roles and titles tend to follow.
3. Do it with a smile.
Sports is demanding. The hours are long. The pressure is real. If you’re going to put in the work anyway, don’t forget to enjoy it. Energy, attitude, and how you show up for others matter more than most people realize.
Feeling Inspired? Check out these opportunities.
-Kyle is actively hiring six (6!!) social media management interns. If interested, shoot him a message on LinkedIn.
Closing Thoughts
Thank you for reading this week’s edition of So You Want to Work in Sports. I appreciate you being part of this community.
If you have ideas, feedback, or future guest suggestions, feel free to reach out at [email protected].
If you want more hands-on support as you navigate the start of your career within sports, book a 1:1 session with me here. The sooner you start preparing, the more confident you will feel when opportunities come your way.
Win the week!
-Ethan
Want more from Kyle?
Connect on LinkedIn
Follow on TikTok
Follow on Instagram
Check out Whittingham Sports
One Habit You’ll Keep
By this time of the year, most New Year goals are already slipping. That’s why the habits that last are the simple ones.
AG1 Next Gen is a clinically studied daily health drink that supports gut health, helps fill common nutrient gaps, and supports steady energy.
With just one scoop mixed into cold water, AG1 replaces a multivitamin, probiotics, and more, making it one of the easiest upgrades you can make this year.
Start your mornings with AG1 and get 3 FREE AG1 Travel Packs, 3 FREE AGZ Travel Packs, and FREE Vitamin D3+K2 in your Welcome Kit with your first subscription.