On Set With Windy City LIVE Associate Producer Jessie Kalin

Watching morning TV in your PJs may be ultra chill, but what happens behind the scenes of your favorite talk show most certainly is not. And because seeing is believing, we spent a day on set with Windy City LIVE's associate producer and modern-day Wonder Woman, Jessie Kalin.
Now, we're busy bees, too — but Kalin accomplishes an impressive list of tasks by the time most of us are finally rolling into work. Still, this confident superstar is able to flawlessly coordinate an interview with a local Project Runway contestant, a tasty chef demo, and a major audience surprise…without breaking a sweat. Oh, and forget running around the set in sneaks — she does it all in an impressive pair of heels. Yep, we told you she was remarkable. Now, turn off the tube, click through, and get ready for one heck of a reality show.
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Jessie is wearing a Trouvé sweater, Citizens of Humanity pants and necklace, and Cole Haan Nike Air booties.

What were you up to before becoming the associate producer for Windy City LIVE?
"Most recently before WCL, I worked at MATTER, the Sports & Entertainment group at Edelman PR. Before that, I was at Harpo doing freelance work for The Oprah Winfrey Show."

Was it always your dream to be a producer?
"Despite having various internships in media throughout college, it wasn’t until I worked at Harpo that I knew I wanted to be a producer. I love the fast-paced environment of this industry."

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Jessie arriving to the set about two hours before showtime.

What's the best part about your job and why?
"I love that that every day is something new. I’m never going to have the same exact segment; each one is unique. But the best part about my job is that through it, I get to meet so many interesting people. Windy City LIVE allows me to work with nationally known designers, singers, actors, chefs, authors, etc., and I can help share their stories. Also, promoting the relatively unknown is something that gets me really excited. We have a platform in Windy City LIVE that showcases talented people who are just starting out. I love being able to help promote such great talent and shed a spotlight on them."

And the worst part?
"Early mornings! On days I have segments, I’m at the studio anywhere from 6:15 to 7 a.m. You would think that after doing it for so long that it would get easier…but for some reason, it never does!"

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Jessie sitting in the green room with current Project Runway contestant Kate Pankoke, a guest on the show that day. Kalin is walking her through the steps of her segment.

How do you go about finding guests for the show and how long does that process take?
"Our bookers Emerald Jane Hunter and Jakki Richardson handle booking all of the big celebrities for the show. They do a fabulous job of staying on top of EVERY single person coming through Chicago. Once they book a celebrity, they’ll pass that contact along to the producer who will handle it from there."

"I’m constantly reading magazines and blogs (like Refinery29!) to stay on top of trends, people, and products. If something strikes my fancy, I’ll reach out to that person to come on the show. It’s all about starting and maintaining relationships so people keep Windy City LIVE in mind the next time their clients are available. For example, I reached out to Bobbi Brown’s people when we first went on the air. She’s a very busy lady, so I made it a point to reach out to her people every couple of months to remind them that we would love to have her on WCL next time she’s in Chicago."

"Finally, a few months ago, they reached out to me to let me know she would be in town, and we were fortunate enough to have her as a guest. In that case, it took two years to book a guest! Other times, I’ll reach out for the first time and wind up booking that person for the show two weeks later. It all depends! Every situation is different."

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What do you do if someone backs out last minute?
"If a planned guest is unable to make it, we have another guest that day do two segments if it’s a fit or have Ryan and Val extend host chat. We’ve also had one of our regulars come on to do a last-minute segment. Our executive producer, Marlaine Selip, is a pro at improvising! She looks at it as a challenge when these types of things happen and knows that we’ll always be able to make it work."

In the makeup room getting a touch-up.

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Signatures from previous guests of the show are all over the makeup and green-room walls.

Were you ever starstruck by any of your guests? If so, who?
"Meeting Jennifer Hudson was pretty fabulous — I’m in awe of her talent. Also, Channing Tatum was pretty great to look at when he was here!"

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Fueled by Starbucks, Jessie is explaining to Pankoke where she'll enter the stage for her segment with Val Warner.
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Jessie is wearing a watch from her aunt and a bracelet given to her by host Val Warner.

On average, how many hours a week do you work?
"Between 50 and 60 hours on average. I usually get in around 6 a.m. and leave around 5:30 or 6 p.m. Sometimes, I get to leave around 3 p.m., so it all evens out."

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Jessie's office space where she spends the majority of her time working on segments.

What's a typical work outfit for you?
"Skinny jeans and a loose top — usually a silk button-up. Depending on the day, I’ll wear boots or pumps."

Where do you like to shop for work attire?
"Handle With Care, Scoop NYC, Nordstrom, and Bloomie's."

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Considering you're running around all day, do you have any go-to shoe brands or styles?
"Cole Haan Nike Air! They’re the best. They have little air pockets and padding — they’re much more comfortable than anything else I’ve found. I’ve got their booties, pumps, and flats and will probably have the next pair that goes on sale. However, I’m pretty sure that collaboration is ending this year, so I think I’m in trouble."
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What type of preparation goes into producing a single show?
"A lot! Once a guest is booked for the show, the producer pre-interviews them. Then we create a note packet for our hosts Val Warner and Ryan Chiaverini for each segment. These packets include all the information they would ever need to know about the guest."

"The producer then puts all elements into the rundown for the segment (photos, video, B-roll, intro and outro scripts, giveaways, etc.) and works with our editor Jared Hoffa to create any video and with the graphics department for photos. Our line producer Matt Knutson works off of this rundown during the live show. Lastly, our staff meets to talk through the show from top to bottom."
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Miscellaneous autographs, notes, and reminders.

What do you normally do for breakfast and lunch?
"If I have time in the morning, I like to sit down at home, watch the news, and have a bowl of cereal. If I’m rushing, I’ll make oatmeal in the office or pick up a breakfast sandwich from Starbucks. Freshii is a lunch staple for me — to the point that I get made fun of for eating it so often! For work meetings, I usually meet people for lunch at Public House or for drinks at theWit."

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Jessie going over the show with hosts and contributors Ji Suk Li, Ryan Chiaverini, Val Warner, Roe Conn, and Mark DeCarlo.

What's the routine like for a producer right before and during a show?
"We start by greeting the guests and rehearsing any performances or demonstrations (cooking segments, performances, fashion shows, etc.). Next, we meet with Val and Ryan to run through the segment and inform them of any specifics they need to know. During the segment, the producer goes into the control room to monitor the segment with the executive producer, line producer, director, and technical director. Then it's just a matter of thanking the guests and saying good-bye!"

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Jessie briefing Val before her segment with Kate Pankoke.

Was there ever an on-air or off-air predicament that required major damage control on your part?
"Thankfully, no major predicaments have occurred. When working on a live show like ours, you are constantly adapting to what is happening both in front of and behind the camera when certain situations arise. One time, I had a celebrity (not naming names!) booked to do two segments on the same day — but decided last minute they only wanted to do one. We ended up just doing one segment (which worked out great) but had to scramble to extend a different guest into two segments."

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In the control room during the live show.

What's the energy like behind the scenes?
"High! We have a lot of fun together and really enjoy each other’s company. It’s pretty much guaranteed that we will end up laughing at some point in our staff meetings. We all work very hard, but we have fun doing it. Producers work in teams of two — and I’m very lucky my producing partner, Dan Barbossa, and I get along so well. He’s a great partner to bounce ideas off of, and I know he always has my back!"

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The audience definitely looks smaller in person than on television!
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Jessie watching the live show from the sidelines.

On a scale of one to 10, what is your stress level like during a show?
"I would say between a six and eight depending on the segment. It’s less stressful to have guests on that have already been on WCL versus new guests. You know how they’re going to gel with the hosts, and they’re back on the show because they did a good job the first time. Fashion shows are always a little more stressful because there are so many elements that go into the segment."

"Regardless, I always get a little bit of an adrenaline rush during any of my segments. You work so hard to put together great pieces so you always want things to run smoothly. Our hosts Val and Ryan take a lot of stress out of it. They’re fabulous at what they do and can handle any situation that might arise on-air."

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It's a wrap!

How do you choose to unwind after a long day or on the weekend?
"On the weekends, I love relaxing over a nice dinner and drinks with my boyfriend, Eli. Our favorites are Le Colonial, La Scarola, Mia Francesca's, and Quartino (a block from our apartment so it’s very easy and always good!). Sunday brunch with girlfriends is a must — there are so many great spots here, so I love trying a new place whenever I can."

"During the week, I either unwind by getting drinks with a girlfriend or taking a workout class. I love the classes at Flywheel and Exhale, but now that it’s so cold out, it seems harder to get to them!"