WANT IN? JOIN THE SILLIEST CREW.

We’re always on the lookout for great teammates! Are you enthusiastic and community-minded? Think you’d crush it with a clipboard or whistle? 📋 (Don’t worry, we don’t actually use those).

Depending on location, we're currently open to hiring:

  • League Hosts - our players ops pros!
  • Social Hosts - aka our hype generators!
  • Web & Graphic Designers - digital, merch, you name it
  • Data & Analytics - ppl who think this is fun >

Have other #skillz? We'd love to hear from you! Tell us why - we can even build a role around YOU!

WORK WITH US!

This site is protected by hCaptcha and the hCaptcha Privacy Policy and Terms of Service apply.

Four young, fun people posing for a selfie with a pickleball court in the background. Four, young cute men posing together on a pickleball court with equipment. Young man playing pickleball on an outdoor court with palm trees in the background, Man playing pickleball on an outdoor court with a fence and trees in the background. Playing in Young woman holding a pickleball paddle on a court with a blurred background. From Silly Pickles pickleball ladder league (the world's funnest pickleball league)
Two men holding pickleball paddles in an indoor setting

BIG TEAM ENERGY

We’re building a team that reflects the kind of community we want to play in - welcoming, diverse, and unapologetically fun.

We’re a little bit remote, a little bit local, and people first, always. Our HQ is in Chicago, but we’re remote where it makes sense! On the ground, our league leads are part coach, part party planner, part local celeb 👋

Whether you're behind the scenes or on the courts, there's room here for you to show up fully as yourself. We’re big fans of people who take initiative, work well with others, and don’t sweat the small stuff. Things won’t always go as planned, but we’ll laugh about it later 😘