Why I Joined PressBox

Why I Joined PressBox

Kevin JacksonMay 26, 20265 min read

When you grow up as a Seattle sports fan, it’s natural to develop a chip on your shoulder.

Out here, we know much of the country views the entire Pacific Northwest as “Southern Alaska,” a dig made infamous by FOX analyst Jimmy Johnson during the 2005 NFL season. (Yes, we remember every slight … even 21 years later.)

Since I was a kid, I’ve yearned for as much coverage of Seattle sports teams as possible. Even in the days when local newspapers were thriving, the hometown papers were never enough for me. And every time one of our clubs got some national recognition, it was worth remembering … and preserving. I still own every Sports Illustrated cover featuring a Seattle athlete since the late 1970s.

Maybe it’s the Seattle fandom that has become a big part of my identity, or maybe it’s because I started my career in small-town newspapers, but I’ve always been obsessed with providing sports fans with as much local coverage as possible. Ultimately, that became a driving force in my career.

We all consume sports in different ways: Unique sets of favorite teams, beloved players and varying levels of passion for the events we follow. For many of us, that usually starts on the local level.

When I was chosen to oversee the launch of ESPN’s local sites initiative in 2008, I brought that same ethos to the first planning sessions for ESPN Chicago. I remember sitting in a conference room and saying, “If we could capture every mention of a Chicago team on an ESPN property — whether it be TV, digital, radio or the magazine — that would make for a great website.”

We built sites in Chicago, Boston, Dallas, Los Angeles and New York with that philosophy — but it was all driven by human editors, making individual decisions. Our teams did outstanding work in those five markets, but the whole ecosystem was built on the video producer watching SportsCenter to spot and clip a Bulls segment, or the editor working on Buster Olney’s column to find a Kris Bryant reference.

When I first spoke to CEO/founder Brian Hough about PressBox, I told him that story about my endless chase to develop comprehensive coverage for local markets. Brian told me how PressBox was founded by former Bleacher Report engineers who couldn’t find enough coverage of Formula 1.

We shared the same quest.

And nearly 18 years after those ESPN planning sessions in Chicago, the technology obviously exists to chase this pursuit in a much more effective way.

Brian and co-founders Andy Crum and Tory Briggs took me behind the curtain and showed me how PressBox was building the tools to capture every piece of relevant media created around an athlete, team, league or sport.

Just as importantly (perhaps even moreso), he detailed how the tools will be used by editors, reporters, broadcasters, producers, media properties and brands to help them do their jobs better. That part is incredibly important to me — especially in 2026 — when the hottest topic in the world seems to be how artificial intelligence is coming for your job.

Yes, I saw the polls this month saying 70% of Americans think AI is moving too fast, and the majority view it negatively (just check out that commencement speech at the University of Arizona).

Still, ignoring new technologies or hoping they slow down is not the answer. Instead, I’m embracing the challenge of helping shape these new tools and making sure they’re used to help journalists, storytellers, fans and decision makers.

PressBox takes that responsibility very seriously — which is why they created my position, Head of Editorial Product, in the first place.

As the fourth employee for a company in its early stages, my job is to work with our editorial clients to make sure their journalistic standards are enforced, all content is properly sourced and nothing here resembles AI slop. Our aim is to create tools that help journalists and marketers create compelling content at scale.

For more than three decades I sat in the boardrooms at ESPN and FOX Sports Digital, and I know how important it is for editorial brands to produce content that is trusted and unimpeachable. (That’s why the word “Editorial” is in my title.)

And, of course, like the younger version of me, we want the coverage we provide to be as deep and broad as possible. Thousands of athletes on hundreds of teams in dozens of leagues. No matter what squads you follow or what sports you care about, we’ll have personalized coverage tailored for you.

That’s why the word “Product” is also in my title, because it will be a moving target to ensure we’re catching all that multi-modal content as quickly as possible without sacrificing quality and still improving the depth of what content teams can deliver. And then we have to deliver it to our clients in a way that helps them move it to their audience with the highest level of efficiency.

It’s a massive challenge in times that demand it. But I felt similarly in the mid-1990s when I left newspapers to join ESPNET SportsZone at the beginning of the online revolution. Or when I was one of the founding editors of ESPN.com’s Page 2 in 2000 as the sports blog era was starting to take shape.

Sports coverage is in a constant state of evolution. Anyone who says they know exactly where it’s going is probably wrong. But I am excited to take this journey and find out.

May 26, 2026