How to Build a Sports Media Empire: An Interview with House of Highlights’ Caroline Jastremski

Mike O’Brien ‘23 

Chief Sports Editor

Sports are a way of life for some people. That’s a fact. It always has been, and it always will be. And for generations now, the landscape of how people consume sports is an ultra dynamic landscape. Whether it be listening to baseball games on the radio in the ‘60s or the birth of NFL Sundays on television, the consumption of sports media has been an ever changing realm present within society at large. Now, enter social media. Almost everyone you know likely has an Instagram, Twitter, TikTok, Snapchat, Facebook etc. account in order to be connected with friends and family, and to stay informed. And sports media has been all over it.

House of Highlights is one such sports outlet that has a massive presence on social media. The page currently has 32.3 million Instagram followers; more than ESPN (22.1 million), Overtime (6.1 million) and CBS Sports (973 thousand) combined. Originally starting out mostly posting NBA highlights when it was founded in 2014, the page has grown immensely, covering a multitude of sports and collaborating with other content creators. 

One of the key players at House of Highlights is Caroline Jastremski, who serves as HOH’s Director of Programming. Jastremski has represented the outlet at numerous high profile sporting events, such as the 2022 NBA All-Star Game, the 2021 MLB All-Star Game, the Jake Paul vs. Tyron Woodley fights, and more. I was able to speak with Jastremski about her experiences with the outlet and how the brand is evolving. 

To get things started, I asked her about what it means to be the Director of Programming and what that entails on a day-to-day basis, to which Jastremski told me “I run a team of about eight. With the director title, it’s really great because I get to wear many hats. Not many directors are going out in the field getting content as well; it’s usually more behind the scenes work, but I think because I’ve expressed that I have a passion for that and I’ve done it in the past I’d still be able to do the things that I really like.

Day-to-day I meet with the sales team, I meet with the programmers individually and as a group, I meet with our production team, and basically we’re just making sure that on a day-today-basis we’re posting to our several social channels. Then it’s just planning for tentpole events, whether it’s an actual on-site event or stuff going on throughout the month and speaking out on things that we should be like Black History Month and Women’s History Month. I have my hands in a lot of different things, but on a day-to-day basis it’s just making sure all my soldiers are in line.”

Following up on the idea that the outlet seeks to incorporate and celebrate many different groups within sports such as their events for BHM and WHM, I asked her if House of Highlights has a “mission statement” that they try to follow in their work. Jastremski answered “I wouldn’t say it’s a mission statement, but I’d say it’s core pillars as we like to call it. We look for moments, whether it’s big picture or everyday, and make sure it’s both celebratory and relatable. We also seek to be the voice of all these different athletes; we can be a platform where they can speak up on things or represent them in a way that their respective league might not be able to.” 

After learning more about House of Highlights in general, I was curious to know about Jastremski’s unique experiences that she’s had while working for the outlet. So, I popped a tough question; of all the events she’s been to so far, which has been the best one? With a laugh, Jastremski said “That’s super hard. I think most recently at the NBA All-Star Game was honestly the coolest experience just because I was able to be around so many different athletes and celebrities at the same time. Seeing LeBron up close was definitely crazy, seeing Michael Jordan up close was surreal; I was in the room for the NBA 75 photo, so I was in the same room as Magic Johnson, and I’m just like ‘Wow. That’s never gonna happen again really.’ 

I’m also a big baseball fan, so the MLB All-Star game in Colorado was also great. I’m a Yankees fan, so my interaction with Aaron Judge was really cool, just because I knew of him more than any of the athletes I’ve met just because I watch the Yankees day in and day out. So I was probably the most starstruck in my conversation with Aaron Judge. Meeting Nikola Jokic and his brothers was great too; he wasn’t what I expected him to be, he was definitely super outgoing and talkative which was great. Every interaction I’ve had with Dwyane Wade has been great too; he does a lot of stuff for us on the TV side on TNT and he’s super humble and kind, and he’s a big fan of House of Highlights.” 

Hearing about her experiences with these professional athletes made me realize that any sports fan in her position would totally be starstruck too; no matter the level of professionalism they put forward. On this subject, I asked Jastremski how long it took her to settle into the fact that talking to athletes on a regular basis was her job now, and how she’s able to not let her fan side get the best of her. She responded “Like I said, I do like basketball, but baseball is my favorite, so it’s such a bigger challenge for the baseball events I cover. Part of me wants to be like ‘I’m a Yankee fan!!’ for fun when I’m interviewing a Red Sox player, but it’s not something that I can really bring to the table. When I talked to Pete Alonso during my interview I was super professional, but then off camera I was like ‘Go Yankees, Mets suck.’ I think players appreciate that authenticity too, but it’s definitely hard, because when I’m at the events, at the end of the day I can’t get too starstruck because it is my job to give viewers the best content experience possible.” 

House of Highlights isn’t just a social media platform either; recently, HOH has collaborated with TNT to sponsor both NBA and NHL games which are broadcasted on the channel. Explaining how this partnership with TNT came to be, Jastremski said “What’s great is we have these internal connections where if you network properly, there’s so many people at your disposal. I networked with somebody at NBA TV, which is under the same umbrella as the NBA on TNT, and we pitched them a way to provide more on-site coverage, and they were looking to implement more social media experiences. We suggested a HOH Fan Cam, where we’d go to the games and get pre game content on the court and filming stuff during the game, and then they’d showcase it on broadcast. On a day-to-day basis, there’s not too much interaction, but for NBA All-Star that’s how we were able to get such great access because it’s a TNT event. We have stuff they want, and they have stuff we want, and we’re learning from each other.”

After hearing about Jastremski’s experience and how both her personal and experiences and the House of Highlights outlet itself has developed, I was interested in what she would tell herself if she could go back in time to her first day on the job, whether it be a piece of advice or encouragement, or if there’s something that she could know to help House of Highlights even more. After some thought, she said “My experience at House of Highlights has been very unique because I worked at Bleacher Report, HOH’s sibling outlet, so it wasn’t too big of a transition. I joined a smaller team, and Omar Raja, who founded HOH, left for SportsCenter two months after I joined. That meant a lot of, and I guess by a lot of I mean all of, the programmers who were at HOH left for SportsCenter too. So it was just me for a couple months; I think during that time it was a lot of hard work, stress, and anxiety. When I got hired, my main pitch was that I was super familiar with the social media landscape, and even since basketball wasn’t my main sport, I was kind of thrown into the fire going from being a contributor to the only person being responsible for the heartbeat of the NBA coverage on our page, which was nerve racking. 

But, I learned a lot, and it taught me more than I ever could if I was shadowing people for a year plus. So, I think if I could tell myself that when I started all that hard work would pay off and that later on I wouldn’t care about the sleepless nights. I think it’s relatable because I started off working for a newspaper in my hometown and it might not have been the dream, but a lot of the stuff I learned there helped me get the job at Bleacher Report; I also worked at MLB for a year doing part time work, so I think every experience is going to set you up for what you’re meant to be doing, and it might be hard to realize it in the moment, but you never know. Take every job you have with pride because you never know where it’s going to lead you.” 

Much like the athletes she’s encountered herself, Jastremski has put in the work, with a team and by herself, to oversee one of the most influential sports media brands in the business. Who’s got next?

Categories: Sports

Tagged as:

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s