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The Art of Event Execution

Rachel Crick recently spoke with Jillian Waitkus, the director of ticket, hospitality & event sales at Churchill Downs on leading an event team and coordinating the moving pieces behind the scenes to keep everything on track.

Jillian Waitkus has been the director of ticket hospitality and event sales at Churchill Downs in Louisville, Kentucky, for three years. Prior to her current role, she worked for the Lexington Legends and the Louisville Bats Baseball Club in marketing and events. She graduated from the University of Kentucky in 2016 with a Bachelor of Business Administration and Marketing. She was recognized as one of BizBash’s Fresh Faces of 2024 and was a finalist in Louisville Tourism’s Rose Awards in 2021 for event services.

Jillian Waitkus

Q: Can you explain the importance of having synergy within an event-planning team?

A: I have a unique perspective because I have seen it from both sides. When I worked with the ballparks, I was selling the events, then planning and executing them, and working with the execution side. That’s housekeeping, the broadcasting team, the A/V team — everyone who is making sure everything goes off without a hitch. That’s given me a little perspective to anticipate some potential challenges. Sometimes the planning team and execution team are two different teams that don’t report to the same person. That synergy you have with operations is the key to the success of your events and pulling off what you say you’re going to deliver. If you don’t have that synergy, you’re going to have a team that lacks direction and feels like they’re not respected or that the other team can’t be trusted.

Q: Are there any areas of the planning process where it can be easy to get out of alignment with your operations team?

A: There is misalignment at a lot of organizations because you lose sight of the greater goal. We want to deliver first-class customer service, so we’re going to do that by knowing we can confidently pull off an event. It starts from the beginning. If you don’t have your operations team involved from the beginning, you’re setting yourself up for a setback. From the time we get the inquiry, we’re having conversations with our entire team. We’re saying, “Here’s what they’re wanting, help me brainstorm options for them.” We have to take them on their first site visit with us because they can help us spot things we can’t see. We’re not necessarily the experts in the operations side, so it’s about keeping them involved from the jump. Even when there’s that stress and anxiety of the event day, you have to remember every detail counts. I’m a huge fan of overcommunicating.

Q: How should planners correct this?

A: A lot of that comes down to being able to set and manage expectations correctly. I want to make sure that my operations team knows I have their back, because there is no good in me landing a big event and us not being able to execute it. The most important thing is to make sure you have a team that feels like they’re being set up for success by the person leading the event. Foster an environment where they’re OK telling you no or pushing back so you guys can meet at the common goal. It’s about relationships at the end of the day, so what I do think people can focus on right now if they’re looking to break into the industry is working on those relationship-building skills. They’re already building relationships with clients and making memories for them. They should take those same basic concepts and work on developing those relationships with the internal teams, whether it’s someone at the venue, contracted vendors or any other stakeholders. It’s building that trust and respect with communication and collaboration.

Q: Do you think this generation has any strengths or challenges when it comes to aligning with their operations teams?

A: One of the biggest teachers in this concept of alignment is just experience, and that’s the hard part. You’re going to learn from your mistakes and shortcomings. This is an industry where you can’t necessarily study this for years and come in and know all these operational workarounds and potential conflicts — it’s something you have to live through. But I think this generation is extremely adaptable, and they’re not afraid to have hard conversations. People feel compelled to share their opinions. That is going to be so necessary when it comes to getting aligned with the operations team or stakeholders. You’re going to have to have those hard conversations.

Q: What role does leadership play in this process?

A: I always like to say, “Lead where you’re at.” It doesn’t matter if you’re a volunteer, if you’re a seasonal helping hand, a full-time representative or if you are a director, like me. You’ve got to be able to identify chances to lead where you’re at by seeking those opportunities to step up and make an impact. That can be something so small. You may see someone that needs a helping hand, and you see an opportunity to step in. Volunteer to lead the charge on or be a part of something. Set a good example by making sure you’re doing all those key relationship-building actions we talked about. It’s about being respectable and building respect, communicating and making sure if there is miscommunication that you’re seeking it out to correct it. It’s about saying, “How can I fix this, how can I make it better?”