Reel Lives: Strive Gaming CMO Jamie Shea On Soaking Up Knowledge, LTVs, And Stray Cats

Brett Smiley

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Every gambler has a story to tell. And so does every person who chooses to make a living in this unique industry.

In our “Reel Lives” series, Casino Reports shines a spotlight on people working in the gaming business, from executives, to analysts, to media members and communications pros, and all points in between.

The subject in this interview: Jamie Shea, a native of Florida who grew up around the horse track and trained to become a schoolteacher before finding her calling  in sports betting. Shea is currently the chief marketing officer at Strive Gaming, following a run as VP of sportsbook operations at DraftKings. 

Casino Reports (CR): Not long after school, you went into race sports league management at Flamingo, your first role in the industry. Was that a role you sought out or something that you kind of stumbled into?

Jamie Shea (JS): You know, it’s funny, my first role in the industry was actually at the Sands under Bob Gregorka. Sheldon Adelson had bought it and it was broken down, like old-school Sands. There were stray cats everywhere. It was just a funny book, and that was my entree to the business. Before that, I had gone to school to be a teacher, but I did my student teaching and said, no, this is not where I want to be.

My dad had owned racehorses when I was growing up, and so I knew horse racing — exactas, trifectas, all that stuff. So I saw an ad for a part-time ticket writer and I went and applied and said, I’m gonna go back to school and figure out what I wanna do, and I fell in love with sports betting. I had some really good mentors in Bob Gregorka, Jack Love, Johnny Avello, and those guys, and they said you have a knack for this, let’s teach you how to book. And so they taught me how to book and I haven’t looked back since.

CR: What’s one of the biggest changes you’ve observed in the actual gambling products today?

JS: Content. It’s the content. If you think back, even pre-PASPA, what you could bet on, there wasn’t that much. The Westgate would come out with their Super Bowl props, and when I was running the Hard Rock we had like six or seven pages of props for the Super Bowl and things like that, halftimes and quarters.

But it wasn’t 24/7 at your fingertips with in-running betting and more. The amount of content makes it so much fun. There’s something for everyone and everyone’s betting style. I love it.

CR: What is an underappreciated challenge, or maybe a misunderstood aspect of leading the company’s marketing team and its initiatives?

JS: You really have to think about lifetime values. You can’t just go and throw money at things. These promotions and bonus programs need to really be well thought-out and conceived. The amount of time and the intensity that you spend getting these to be really good, solid promotions that are fair and good for the customer. But also bring people in to see your product and see how good your product is.

It’s a lot of work and I think that people have a misunderstanding that these things can be produced haphazardly. Especially when I was at DraftKings, we would spend months coming up with different promos, asking, how do we do this? What do we want to do with this? And so I think it’s misunderstood how much time and energy goes into that kind of marketing and the retention and acquisition marketing.

CR: That’s kind of what you’re involved in now at Strive Gaming, right? With the player access management?

JS: With Strive, we have a platform that everything runs through, so content runs through it, too. It’s integrated with pretty much everybody. KYC payments for fraud. It’s got the marketing pieces of it. You can do bonuses, you can do targeted bonuses. It really helps you to create an efficient spend with a holistic view of your customer. And we make it all nice and tidy for you where it’s one back office and you get a holistic view of everything going on with your business in one really good location, easy to use, easy to access, and easy to build promotions and bonuses.

CR: What’s a valuable lesson you learned early in your career that you’ve carried with you?

JS: A good lesson I learned was you don’t know everything, and you should be learning from everyone around you, especially when you’re younger and even if you went to school for this. Don’t assume you’ve got this, that you understand this. It’s not necessarily true, so always be open and willing to hear other people’s ideas. And you may not have the best way to do something, and somebody sitting in that room with you does. You don’t have to be the smartest person in the room — have the smartest people in that room with you. 

CR: How do you like to spend free time away from work? Any interesting hobbies or secret talents?

JS: My husband and I are big foodies. We love trying different Michelin restaurants, we have put a budget together for trying different restaurants. And we love the outdoors, hanging out at the pool, nice kind of kick back, and traveling to Florida where I grew up and visiting with family. 

Reel Fast

Favorite sport to watch and favorite sport to bet on, if not the same?

Football to watch, tennis to bet.

Who’s another person in gaming who has your utmost admiration?

Anika Howard (of Wondr Nation)

What’s the most ridiculous thing you’ve ever seen at a craps table, whether dealing or playing?

Boy, the level of intensity at craps … I’ll say, when people don’t really understand what they’re betting and you see them bet against themselves and they have no idea.

First vehicle you drove?

Pontiac Sunbird.

We know you like fine dining, but, favorite fast food joint?

I love fast food too and I’m kind of old school here. I love Arby’s.

Last book you read?

So, I’m a big fan of memoirs. The last one that I read was actually Matthew Perry’s memoir.

Favorite non-gambling thing to do in Las Vegas?


Which musician do you spend the most time listening to?


Your best bet to find Jamie is at the sportsbook, poolside, or at a Michelin restaurant, and if you’re into LinkedIn, you can look here.

Previous installments of Reel Lives:

OpenBet’s Jess Feil On Player Protection, Running An International Team, And Riding Horses

Fanatics Betting & Gaming’s Scot McClintic On Building Products, Quantitative Thinking, And Hockey Fights

SBC’s Sue Schneider On The Interactive Gaming Council, Mentoring, And The Mississippi River

PrizePicks VP Of Communications Elisa Richardson On Dated Tech Stacks, Sustainability, And Atlantic City