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November 7, 2025 19 mins

If you’ve ever had an event day spiral into chaos and somehow still pulled off magic, this one’s for you. Host Megan Martin sits down with Jessie Smith, Event Manager at Enterprise Events Group, who’s known for delivering high-stakes programs with poise, precision, and serious production chops.

Together they laugh about the real life chaos of event planning like sprinklers going off in the middle of an event gala dinner and discuss why the post-COVID event timeline still gives planners nightmares.

Plus, they play Run of Showdown. The rapid-fire game of planner instincts that’ll have you shouting your own answers out loud.

What you'll learn in this episode:

  • How Jessie accidentally launched her career running a hotel sales office in college

  • Why she went back to school for both undergrad and grad degrees in event management

  • The event that went off the rails when a key team member ended up in jail (yes, really)

  • Murphy’s Law in action: mud pits, busted sprinklers, and keeping guests calm

  • The “tight timeline trap” and how the industry still hasn’t recovered from it

  • The Run of Showdown game: VIP seating vs. GA, selfie stations vs. step-and-repeats, and more


About the Guest:

Jessie Smith is an Event Manager at Enterprise Events Group, known for her ability to keep cool under pressure and execute global programs seamlessly. She’s a Certified Meeting Professional, Virtual Event Producer, Event Strategist, and lifelong events enthusiast.


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https://msquareddynamics.com/

Connect with the Guest

https://www.linkedin.com/in/jesssmith1031/ 

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