Meet Jessa Maddocks the founder, CEO and Creative Designer of JessaKae

  • Published on:
    July 20, 2022
  • Reading time by:
    5 minutes
Meet Jessa Maddocks the founder, CEO and Lead Designer of JessaKae

Meet Jessa Maddocks the founder, CEO and creative ead designer of JessaKae, a dress and mommy-and-me brand that focuses on making women of every size feel elegant and powerful. With her entrepreneurial spirit, Jessa combined her love of photography, fashion and design to create JessaKae in 2016, and continues to champion size inclusion in her clothing.

‘’I have always loved fashion, design and photography, and combining all those passions together into one business seemed really intuitive. And I wanted to create clothing for women that were romantic and unabashedly feminine. There’s something so powerful about a woman who owns her femininity and her beautiful body, and I wanted to create a brand that celebrates her.  As I was starting JessaKae with my husband, I noticed a large population of women was massively underserved in the fashion industry because brands didn’t carry inclusive sizes. I wanted JessaKae to be a place where all women felt gorgeous at any size, so we made it a core value at JessaKae to provide our dresses in sizes ranging from XXS to 6X, always.’’

A soup-to-nuts executive, Jessa designs fully original collections and directs all product photoshoots. Jessa lives in Utah with her two sons and husband, Jordan Maddocks, President of JessaKae. Women On Topp spoke with Maddocks about her experiences as an incredibly motivated, business-minded woman.

How did you first become interested in working for yourself?

I’ve always been an entrepreneur, even since high school. I loved being able to schedule my own hours and craft and execute my own vision. Having full autonomy over the creative process, from beginning sketches to final product photoshoots, gives me life. Before founding JessaKae, I had my own photography business and learned so many valuable lessons that have helped me in running my current company. My husband and I also have a kids’ clothing company called Loocsy that specializes in playful, comfortable clothes. Diversifying within the fashion industry is so fun for me. Once you catch that entrepreneurial bug, it’s there to stay. 

Tell us about your work. How did you decide to take the leap to work for yourself? What are some of the greatest accomplishments thus far? Any particular challenges someone should think about before trying to go out on their own?

There’s never going to be a “perfect” time to go out into the unknown and start your own company. You just have to take that leap. I started JessaKae, with the help of my husband, in our basement apartment. We didn’t have a fancy warehouse, and even replaced all of our furniture with warehouse shelving. It was quite the circus. But it was so beneficial for us to work as lean as possible to avoid all the traditional overhead. Operating lean meant that we could continue to buy additional inventory, scale faster and take bigger risks. That’s a challenge women should focus on as they start a fashion brand – navigating how to stay lean. 

I am so proud of JessaKae’s evolution and growth. Now we produce more than 12 dress and mommy-and-me collections a year with only original designs in inclusive sizes, with separate collections to come later this year. We’re also extending into accessories like headbands and hair bows and collaborating with amazing companies and influencers. We now have a big warehouse and a storefront and ship in all 50 states and to 40 countries. We are a fully female-run and operated business with 12 employees that I love and consider family.

What aspects of your education and training have been most crucial to your success? Give us some examples of the day-to-day processes as fashion brand owner. Do you have to maintain continued education requirements?

Fashion is always evolving, and as the creative director of JessaKae, I need to constantly be dialed into fashion’s trends and transformations. While there aren’t any specific continued education requirements, in the words of Heidi Klum, “one day you’re in, and the next day, you’re out.” If you want to stay relevant — or “in” — you have to predict shifts and alter your product accordingly. It’s a fine line between listening to those outward voices and staying true to your internal design aesthetic. To me, it’s vital that each piece we design at JessaKae still embodies our values and isn’t solely determined by the current fads. 

My photography background has been crucial to the success of JessaKae, as I direct all of the product photoshoots for each collection. Planning these collections — from the color palette to the fabric to the photoshoot locations — is a large part of my day-to-day process. I love my job. 

Do you have any tips on how to start a fashion brand? 

The main tip I have is to not spread yourself too thin with your product offerings. We originally started JessaKae as a boutique, offering way too many products from other companies, like tops, bottoms, shoes, you name it. After nearly a year of this, we realized we needed to simplify and whittle down our brand to its core essentials: we wanted to make dresses for women that made them feel beautiful. Carrying other people’s designs, with inaccurate sizing and a huge range of quality, didn’t align with this mission. So our secret sauce was to focus on one main product, master it, and then build from there. 

How do you balance work-life? 

This is always such a hard question! But what I’ve come to know is that balance is an illusion. Sometimes you have to devote all your time to your business, especially in the beginning. You have to dive in head first and rely on your support team to pick up the slack in the other places. As women, it’s often so difficult for us to ask for help. We have a “you can do it all” mentality, but that also is a lie. You need a good support team to help you as you embrace that initial grind. I have spent countless sleepless nights perfecting products and figuring out solutions to unforeseen roadblocks. Starting and running a business takes your blood, sweat and tears, and there’s no avoiding that. 

As JessaKae has scaled to the next level and we’ve built out our team, I’ve delegated responsibilities, which has helped my work-life balance hugely. Now I’m able to block off family time whenever I need/want. Hello mommy-son vacations to Disneyland!

Who are your clients? 

I feel so lucky that we’ve built a strong community of women who love to feel girly! We keep our ear close to the ground for what our community wants, and often ask them to review our dresses so we can make them better. Our JessaKae woman looks for original, beautiful statement pieces that command a room and are made to last. She is sophisticated, elegant, adventurous, creative and feminine. She enjoys the simple pleasures in life, like strolls in the park and picking wildflowers, and is a hopeless romantic to her core. 

Who have been your own biggest mentors and what is the best advice they have ever given you? 

I’m lucky to have such a great network of friends and powerful women who have helped me and believed in me. One of the best pieces of advice I’ve been given was from my friend Courtney who told me “Dude just try a floral dress, I promise you it works and people love it.” The first floral dress I carried became a viral sensation and I’m so glad I took her advice on that! I also love Jessica Alba and take a lot of inspiration from The Honest Company’s path to success. Crossing my fingers that one day we’ll meet and become fast friends! 

If you could go back and tell yourself one thing before beginning your career what would it be? 

The one thing I would tell myself is to believe in myself! Haters are always going to hate. You’re going to face naysayers trying to hold you back. I urge female founders to not let pushpack or negative comments influence them, whether that’s from competitors, customers, or especially social media. The world needs you and your vision. There’s room for all of us. 

What are you working on currently and why?

We have so many irons in the fire right now, which is such an exciting position to be in. We’re working on expanding the JessaKae brand with collections for special occasions (think bridal, wink wink) and the bedroom (think comfy, cozy!). We’re also working on expanding our sizes to include 6X because we want ALL women to be able to wear our dresses and feel amazing. We’re one of the only brands based in Utah that carries sizes bigger than an XL, which is truly alarming to me, and we want to pave the way for more size-inclusive fashion. 

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