Becoming a Digital Sponsorship Expert with Alex Kopilow.

Meet Alex Kopilow.

Alex is the founder of Sponcon Sports, a weekly newsletter read by more than 3,500 sports executives around the world. He is also one of the most trusted voices in digital sponsorship and content monetization, with experience spanning the Chicago White Sox, Madison Square Garden Sports, the New York Mets, and multiple agency environments.

But Alex’s career started with a very different dream.

Coming out of Ohio State, Alex wanted to work in sports media. Specifically, he wanted to be on television. He chased that path the way many young broadcasters do, by saying yes to any opportunity that would get his foot in the door. That included packing up his life to move to Sioux Falls, South Dakota, staying in the living room of an old fraternity brother, and taking an internship, that didn't require receipt of college credits to kick off his career.

Not glamorous by any standard, but it worked.

Over the next six years, Alex built his career as a sports journalist and broadcaster, working in small markets across the country. He covered high school sports, college athletics, and the occasional professional team. He shot, wrote, edited, and reported his own stories, anchored shows, and traveled frequently.

Eventually, though, the reality of the lifestyle set in.

Alex loved the work, but the hours were long, the pay ceiling was low, and the long-term outlook did not align with the life he wanted to build. He and his wife began talking seriously about what was next. She was from the Chicago area, so they made the move back, and Alex decided to pivot, fully aware that it meant starting over.

So, at 27, he took a paid internship at a public relations agency.

On paper, this could be viewed as a step backward, but in reality, it was one of the most important steps forward for his career.

Alex’s internship served as a crash course in the corporate marketing and partnerships world. He learned how agencies operate, how to communicate with clients, how to manage timelines, and how to justify strategy with data. He learned digital and influencer strategy, paid media, analytics, and how brands think about return on investment. Over the next few years, he worked across three different agencies, gradually expanding his responsibilities and sharpening his skill set.

One important detail is that much of Alex’s agency experience came outside of sports, but in many ways that proved to be an advantage. Those years prepared him just as well, if not better, than a traditional path inside the industry. By the time he was interviewing for a digital partnerships role with the Chicago White Sox, Alex could bring forward a perspective many candidates could not, holding a firm grasp on brand objectives, operational functions, and sponsorship measurement.

After a quick interview process, Alex was offered and accepted that role with the White Sox, completing his career transition from sports journalism to sports partnerships. During his season and a half with the club, he helped drive significant growth in digital revenue and worked closely with leaders from both the White Sox and Chicago Bulls (same ownership), gaining exposure to how elite organizations structure their digital operations. It was a dream role, combining content, partnerships, and measurable business impact in a way that felt perfect for his skill set.

The experience opened the door for his next opportunity with Madison Square Garden Sports, where Alex moved into a senior role supporting digital partnership solutions across the Knicks, Rangers, and other marquee properties. It brought him closer to home and into one of the most high-profile environments in sports. Larger scale and higher expectations, it was the perfect next step. He spent just over a year with the property before they transitioned their partnership team to an outside agency. The restructure eliminated Alex’s position.

This was a setback, of course, but Alex was prepared.

Digital partnerships focus on how teams, leagues, and media companies generate revenue through their owned digital channels. This includes social media, websites, mobile apps, email, SMS, and emerging platforms. Professionals working in digital partnerships sit at the intersection of content, marketing, data, and revenue, designing sponsorship programs that feel native to the fan experience while still delivering clear value to brand partners. The goal is not to place ads in feeds, but to create content and campaigns that audiences actually want to engage with, then tie that engagement back to measurable business outcomes.

The role requires constant collaboration. Digital partnerships leaders work closely with content and creative teams to ensure ideas align with the brand and platform best practices, while also partnering with sales and account teams to price, package, and activate inventory effectively. A day might include building new digital sponsorship packages, analyzing performance data, educating partners on why certain strategies work, or helping internal teams rethink how digital assets are valued. The space moves quickly as platforms evolve, fan behavior shifts, and measurement expectations increase. Those who succeed are fluent in digital strategy, comfortable with data, and able to translate between creative storytelling and commercial impact.

In January 2023, 8 months before his layoff, Alex committed to posting on LinkedIn three times per week, building on a more informal and inconsistent writing habit he had previously maintained across Twitter and LinkedIn. That consistency helped him to begin building a personal brand, with his posts gaining steady traction across the platform. After his layoff, with encouragement from a friend, Alex leveraged that foundation to launch Sponcon Sports, a weekly newsletter breaking down sponsored content strategy in the sports industry through case studies, influenced by his own point of view.

The launch was a success, and over time, the newsletter became another lever in building Alex’s personal brand, one that quietly created new opportunities.

First, just months after being laid off from MSG, a reader referred Alex internally to The Arena Group, where he took on a senior role in digital partnerships, helping drive seven figures in revenue across major media brands. Later, subscribers from the New York Mets reached out and asked him to audit their digital monetization approach. Alex did the work without charging for it, knowing the opportunity it could create. And he was right.

The audit led to a one-year contract with the Mets as Director of Media Partnerships, where he brought the recommendations from his audit to life, taking the organizations digital deals to new heights, resulting in a double-digit increase in year-over-year revenue.

Which brings us back to the present. Alex’s contract with the Mets ended last month, but it is clear that his work in the space is just beginning. He is continuing to grow Sponcon Sports, shaping the future of digital partnerships within sports, and has even bigger plans for the rest of the year.  He's scaled the newsletter into a digital consultancy that helps pro teams and leagues identify undervalued or overlooked digital inventory, particularly in organizations where content and sales operate in silos, so they can unlock meaningful revenue without burning out their staff.  

His story is a testament to the value of going all in, the power of working hard and learning along the way, and the opportunity that comes from being visible. Do it right, and you just might end up with a career like Alex’s.

Q. Developing a personal brand has opened doors for you at multiple points in your career. Why has it been so valuable, and how can students and young professionals get started in building their own?

A. I’ve been sharing my thoughts on social media strategy and digital partnerships since 2021, first on Twitter, then LinkedIn, and now through my newsletter, and it’s played a role in landing my last four jobs. It’s been valuable because it shows my interest in the space outside of work hours and signals the level of thoughtfulness and enthusiasm I bring to my roles. It also demonstrates that I can build an audience, clearly articulate my point of view, and defend my opinions, which matters in any professional setting.   

For students and young professionals, the best part is you can start today. Don’t worry about performance or going viral early on. The key is making content creation feel like a natural part of your routine. Years ago, I challenged myself to write on LinkedIn at least three days a week, and now coming up with ideas feels much less overwhelming. After you’ve been consistent for a month, you can look back at what resonated and start optimizing from there.  

Q. There’s a common misconception that if you don’t begin your career in sports, you’ll never be able to break in, but your agency experience was critical in preparing you for roles on the team side. What advice would you give to others looking to make a similar leap into a career in sports?

A. The sports industry is extremely competitive. You can’t control when you break in, but you can control how prepared you are when the opportunity comes. Start by getting clear on what you actually want to do in sports. You don’t need to work in sports to build those skills, and you can be involved in the sports business without working directly for a team. There are leagues, agencies, brands, tech companies, hospitality groups, plenty of paths in.

Networking also matters, but it needs to be done well. Reach out to people on LinkedIn when you don’t need anything from them, and ask something specific about their role or experience. Avoid vague asks like “picking your brain.” People are generous with their time when it’s clear you’ve done your homework and know what you want to learn. Also, be active in LinkedIn comments, especially if posting feels intimidating. Thoughtful comments can get just as much reach as posts, and once people start seeing your name regularly, cold outreach becomes much warmer. Just skip comments like “totally agree” and aim to add something meaningful, even if it’s just a smart question.  

Q. You’ve established yourself as an industry expert in digital partnerships. What skills matter most in this space, and how can someone early in their career start developing this skill set?

A. I spend a lot of time studying sponsored content, roughly 10 hours a week between scrolling and writing, and that’s helped me develop a strong sense of what works and what doesn’t. That said, the soft skills matter even more. I’m very solutions-oriented. I never shut down an idea outright. Instead, it’s usually, “We can’t do this because X, but we can do Y, and here’s why that approach still achieves the goal.”

Being an expert also means being a teacher. It’s not about saying “listen to me because I know the most.” It’s about being approachable and helping teammates and brand partners understand the space without making them feel talked down to. A big part of the role is acting as a connector across departments, which means building trust and knowing how to work well with different teams. On top of that, you have to be detail-oriented and organized so you can track partnerships, answer questions quickly, and communicate clearly. Your teammates should never have to wonder where things stand or what the next steps are.

1. It’s Never Too Late to Pivot
Alex restarted his career more than once, including taking an internship later than most would feel comfortable doing. Each move was intentional. If the path you’re on no longer fits, changing direction can be the step that unlocks long-term growth.

2. Personal Brands Create Leverage
Consistent writing opened doors that applications never could. Alex’s visibility led to referrals, conversations, and new roles. A personal brand doesn’t need to be loud. It needs to be useful, consistent, and built over time.

3. Skills Transfer More Than You Think
Agency experience outside of sports gave Alex an edge when he moved into digital partnerships within sports. Understanding brands, data, and measurement matters. If you can clearly connect your skills to the problem, the industry is more open than you might think.

-Manager, Partnership Strategy | University of Kansas

-Editor, Partnerships & Marketing Media | Premier Lacrosse League

-Spring Intern, Global Partnerships - Data & Research | AEG Worldwide

-Intern, Global Partnerships | UFC

-Partnership Marketing, Seasonal Assistant | Kansas City Chiefs

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.

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