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Event Inspiration/Articles/Planning/Wedding Planner Spotlight: Cherry on Top

Wedding Planner Spotlight: Cherry on Top

Marta Block


One of the great things about GigMasters is that we get to work with clients planning important events, as well as event professionals. As often as possible, we try to get the two together so that they can learn from each other. Our sister blog, Life of the Party, recently ran a version of this interview with event planner Jessica McIntosh of Cherry on Top Events in Wisconsin.

GM: How did you get started as a professional event planner?

JM: I actually got started in event planning without really knowing it was happening. As a Human Resources professional, I spent a good deal of time planning corporate functions: off-site conferences, holiday galas, corporate picnics, etc. In my free time I volunteered for 2 local foundations as the chair of the decoration committee. During a Havana Night Gala in July 2010 I was approached to plan a private event for a guest in attendance. Almost overnight I formed the Cherry on Top LLC and started booking weddings for summer 2011!

GM: What types of events do you typically plan?

JM: 90% of my business consists of weddings in the Lake Geneva, WI market. However, I have experience with destination weddings as well. I also enjoy the opportunity to go back to my roots and plan off-site corporate functions.

GM: What sets you apart from other event planners?

JM: I think my business is successful due in large part to wonderful referrals I’ve received; which I attribute to a keen eye for the smallest of details and my ability to stay calm in the chaos of a wedding weekend. For example in June 2010 the power went out as the bride and groom stepped to the door for their grand entrance. It was far from ideal, but with a little creativity, a few flashlights and an extra glass of wine for the bride…spirits remained high and the evening went on to be fabulous!

GM: What is your favorite part about being a professional event planner?

JM: Every day I “go to work” is the best day of somebody’s life. Not many people can say that.  Being close to a couple during the planning offers a private glimpse into what many couples do not let outsiders see. It is a way for me to know the couple on a level that in the end allows me to capture the elements that truly reflect the things that make the couple unique.

GM: How does entertainment fit into the events that you plan?

JM: Entertainment is such a HUGE reflection of the couple. The entertainment plays such an important role in setting the tone on their big day. I personally love music; and I think the best wedding ceremonies incorporate music into the program. Live music creates an environment of romance and intimacy during the ceremony; and what is better at a wedding than romance and intimacy? Likewise, the music at the reception often sets the tone for the evening. My best advice is to select entertainment that sets the energy and tone that you want for your event.

GM: Why do you use GigMasters for finding entertainment?

JM: GigMasters is a great way to narrow your entertainment search to find exactly what you are looking for. For example; in June 2011 I planned a benefit Gala in the Lake Geneva area with a Memphis Blues theme. I was able to quickly identify Blues bands in the greater Chicago/Milwaukee area, listen to demos, watch live videos for events and contract the vendors for a quote. When there are SO many little details to event planning; I think it is wonderful to have such an easy process to check entertainment off of the ‘to do’ list.

GM: What’s the biggest misconception people have about event planners?

JM: People often assume that event planners are too expensive or are only associated with high-end weddings. I built my business model around making my services applicable and affordable to a wide audience.

GM: What’s the biggest mistake people make when planning a big event on their own?

JM: There are so many unforeseeable obstacles that present themselves. Most people planning their own events don’t build the time or resources to handle the unforeseeable in their event plan. And, if they do build in the time/resources; even after dealing with the issue they have a difficult time recovering and moving on. As an event planner it is my job to be aware of the problem, develop a solution, execute the solution and move on; the bride or host is often not aware that a problem existed. This is how I measure personal success.

GM: What’s the one piece of advice you’d offer anyone about finding a planner?

JM: Meet with the planner and spend some time talking about yourself: your vision, your likes, your style, etc. Similarly, ask the planner to talk about his/her style. Tell the planner your idea/theme for your party and ask him/her to shoot from the cuff to offer ideas/vision. Make sure from the beginning that you have compatible styles/visions for your big day

GM: What’s one piece of advice you’d offer anyone planning a party on their own?

JM: Hire an event planner; lol. But if you do decide to do it on your own; remember to keep it fun! I always tell people not to get so caught up in the planning and the details that you forget to enjoy the party. Likewise; if you are planning a wedding…remember not to get so caught up in planning the wedding that you forget to plan for the marriage! A wedding is a beautiful day in your life, but in the end it is just that…1 day. Spend your year enjoying each other, learning more about each other and planning an event that celebrates your love and the life you are building together!

To read the complete interview visit Life of the Party. If you are interested in working with Cherry on Top Events you can contact them at (262) 203-5552 or at Jessica@cherryontopevents.com. You can also learn more about this wonderful company on their website or Facebook page.