The Work in Sports Podcast - Insider Advice for Sports Careers · Brian Clapp - Work in Sports

Jobs in Daily Fantasy Sports are a SAFE BET w/ Dylan Cooper Senior VP at PrizePicks

·35 min·2 clips

COVID cut PrizePicks' revenue overnight, forced layoffs, and pushed the company into cornhole and esports.

Fantasy sports is not new here, and Brian opens by admitting he did not realize it went back to the 1960s. That quick history note leads into a sports career conversation about where fantasy sports sits in the industry now. PrizePicks is the live example. Dylan talks about joining early, when the app had 10 customers a night and the company was still finding its legs. That makes the career advice feel earned. The best story is about a candidate who noticed a support problem and said, plainly, that he could fix it. Brian likes the move, but he does not sell it as universal advice. He points out that this kind of bold pitch works better in startup culture than it would in every sports organization. The lesson is not swagger for its own sake. It is showing an employer that you understand the problem behind the opening. Dylan's example gives that idea some bite. The candidate was direct, maybe a little cocky, but he brought a solution instead of vague interest. That changed the room. PrizePicks hired him, and Dylan says he became one of their best hires over the last couple of years. Brian then turns the story back toward listeners: openings exist because something needs help, so lead with the problem you can solve. The episode also spends time on what makes PrizePicks different and why Dylan has pride in the business. Brian closes with a useful joke about never being good at fantasy sports, even though people expect more from him because he works in sports. That keeps the door open. You do not have to dominate fantasy sports to see the jobs around it. Tech, analysis, and content all come up as credible lanes in a part of sports Brian says keeps growing.

As heard by us

A grounded look at sports-tech hiring, fantasy sports growth, and problem-solving as a career signal.

Brian Klapp and Dylan Cooper treat daily fantasy sports as more than a pastime, framing it as a real path into sports work. The conversation moves from the growth of fantasy sports to a practical question for listeners: how to stand out when a company is hiring for a specific…

Read the full review in PlayNext →

Why you'd press play

You want a clearer path into fantasy-sports careers and hiring.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from The Work in Sports Podcast - Insider Advice for Sports Careers