Sales Kickoff Entertainment: Start Your SKO with Real Energy

Your sales team has sat through enough keynotes. SideHustle LIVE brings comedy, competition, and real energy to your next sales kickoff.

Event Guides
SideHustle LIVE
March 5, 2026
4 min read

Your Sales Team Has Seen Every Motivational Speaker

Sales kickoffs are supposed to fire up your team for the year ahead. But after the third keynote and the second breakout session, your top performers are checking email under the table. The entertainment portion of your SKO is your chance to reset the room's energy — if you choose the right format.

Why SideHustle LIVE Fits Sales Teams Perfectly

SideHustle LIVE is a comedy game show where entrepreneurs pitch side hustles to comedians. Sales teams love it because:

  • It's about pitching. Your team lives and dies by the pitch. Watching entrepreneurs pitch to comedians — and watching what works and what doesn't — is both entertaining and oddly relevant.
  • It's competitive. Audience voting and the "Funny or Fundable" format taps into your team's natural competitive energy.
  • It's high-energy. Professional comedians keep the room at a level of energy most keynote speakers can only dream about.
  • It can feature your team. Our most popular SKO activation: have your sales reps pitch their own side hustle ideas on stage. It's hilarious, bonding, and reveals a side of your team you've never seen.

SKO Booking Details

SideHustle LIVE produces custom shows for sales kickoffs across the US. We've worked with teams from 30 to 500+ and can tailor the format to your event's theme and agenda. email team@playsidehustle.com.

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