Jayna Cooke of Closet Angels

By the age of 31, Jayna Cooke has held the title of Miss Teen Michigan, district sales manager and fashion buyer for Neiman Marcus, Regional Manager at Echo Global Logistics, and Vice President of Business Development and top-earning salesperson at Groupon, the Internet’s daily deal phenomenon. Once responsible for managing Groupon’s largest book of business, she was the one woman who accounted for 25% of the company’s entire revenue, having successfully secured partnerships with two of the biggest retailers in the fashion world—Gap and Nordstrom. She further catapulted Groupon to fame when she landed the company’s placement on Oprah Winfrey’s esteemed list of “Favorite Things” in 2010.

Having recently made headlines at Forbes magazine and the Wall Street Journal with her departure from Groupon, Jayna is now re-focusing her enthusiasm and passion for the start-up world through philanthropic efforts that are closer to her heart. As founder of Closet Angels, a non-profit organization benefiting St. Jude’s Children Research Hospital, Jayna’s partnership with the nationally-recognized premier pediatric research and treatment facility encompasses her family values and desire to always do more for others. By accepting gently-used luxury items that are then marketed and sold, one-hundred-percent of all proceeds are given directly to the hospital.

It was a natural transition for her to take the leap to begin her own company. Although leaving a job can be one of the more difficult decisions (as some of us Everygirls may know), Jayna reached this point in her career by trusting in herself rather than giving in to the expectations of others, something she continues to remind herself to do each day. Today, Jayna shares with The Everygirl how creativity, determination, and a willingness to transcend the typical 9-to-5 hours are absolutely necessary when navigating the world of start-ups, and that challenging yourself is the best thing to do for your career.

Full Name: Jayna Kathryn Cooke
Age: 31
Current title/Company: Founder of Closet Angels
Educational background: Bachelor of Science in Business from Miami University of Ohio

What was your first job out of college and how did you land that position?
I was a nanny for one of my best friends and her three boys in Birmingham, Michigan. Her husband, Jason Woolley, played in the NHL so with three very active young boys, she needed an extra hand. It’s crazy when I look at the boys now—Carter (15), Nolan (13 in March), and Fletcher (5)—because they are so big and manly. It was one of the best times of my life. I love everyone so much in that family, and I love their dynamic. Danica and Jason have one of the best marriages, and I look up to them in so many ways. We still talk all of the time. Last year for spring break, Danica asked the boys what they wanted to do, and they wanted to come to Chicago to visit me. It warmed my heart, to say the least, when they came to visit.

How did you make such a drastic career change from nannying in Michigan to transportation and logistics with Echo Global Logistics in Chicago? What previous relevant experience did you have, if any?
Long story! I have been working since I was 14 years old. I have done everything from being a drive-through manager at Wendy’s, a lifeguard, and a swim coach. In college, I managed a clothing store, waitressed, was Hall President of my dormitory and even played water polo for two years. I was also Miss Teen Michigan, District Sales Manager and Buyer for Neiman Marcus, and much more! So although I had never been in logistics before, I felt that my vast background gave me great and well-rounded experience that could transfer over.

What type of work did you do as the Regional Manager of Echo Global Logistics?
Everything from making sure my team showed up for work on time to problem solving when something went wrong. In the freight world, that unfortunately happens often because you work with so many types of people. One minute, I could be speaking with the CEO of a multi-million dollar company, and the next minute, I could be calling a truck driver frantically to see where the truck is and why they were not at the drop-off location. The freight world is very rough around the edges. It definitely taught me how to work with many different people and in varying situations, more so than anything else I have ever done.

During your time with Echo Global Logistics, what do you attribute to your successes in moving up in the company to become Regional Manager? How were you able to uphold the title of top salesperson during your four years at Echo Global Logistics?
A lot of long hours and hard work! One of the founders had secured an exclusive contract with a company guaranteeing a certain amount of revenue based on volume of shipments over the course of a few years. After being with Echo Global Logistics for over a year, I decided I would try the same concept, which makes it easier for both companies in the long run. I ended up having great success with that. To bring multi-million dollar companies on board with predictable shipping patterns and revenue stream was key to our success. Also, I would say my eagerness to learn and always wanting to try something different. I do not like to do the same thing day-in and day-out so I was willing to put in extra work, stay the extra hours, and go above and beyond.

Tell us about your experiences as Vice President of Business Development for Groupon. What would you consider to be your greatest accomplishment at Groupon?
There is not enough time to cover it all! I was blessed to be able to spread my wings and explore what I found was important to a company. Of course, the number one key to success is being able to generate revenue, so that was always the focus. Once we saw we had a working business model, expansion to other markets was the next step, and we did it fast! I remember thinking to myself, “Wow. We have 100,000 people that are interested in what Groupon is doing and in receiving emails from us every day.” That seemed crazy at the time and was so exciting. Geographic expansion was also important, as were key partnerships. I developed relationships with some of the largest names in the U.S., from Gap and Nordstrom to Oprah and Forbes. I looked at everything from partnerships with Nascar and non-profit organization Kiva, to the number of necessary salespeople per market and how many markets we could expand into.

I think my greatest accomplishment was the amount of revenue I generated for the company. I was always the top producer, at one point bringing in 25% of the entire company’s revenue and 10% the following year. When I left Groupon in October 2012, there were over 12,000 employees!

How did you know it was the right time to leave Groupon, a company where you had been so successful?
It was really tough to come to that decision, but I have always enjoyed the start-up world and the early stages of a company where I can really spread my wings and be creative. Once Groupon and Echo Global Logistics reached the level of going public, it was best for me to move on to the next challenge.

Sales is an extremely demanding career. What advice do you have for women who want to break into the industry? What specific skills and personality attributes do you believe are required to succeed?
First, you need to understand what you want and what your goals are. For me, it’s not necessarily a competition and about being at the top, but more or less of a personal challenge. There has always been something inside of me that wants more, business-wise. I have never not been number one in a company. You also have to be authentic.

What are some of the most valuable lessons you’ve gained from working at two start-up companies?
First, there are a million ideas, and execution is going to be the one thing that will differentiate you. I learned to trust myself and to go after whatever I believe is valuable, even if others may not agree with it or think it cannot be accomplished. If I had listened to others, I would not be where I am now.

How did you decide to start Closet Angels, your non-profit foundation? Have you always been interested in non-profit organizations? How did you decide to partner with St. Jude Children’s Research Hospital?
I have always been interested in the charitable space but have a love/hate relationship with welfare. I wanted to create something that was easy for others. For me, it was about taking an under-utilized resource (clothing and accessories that are no longer worn) and turning that into something meaningful, such as funds and resources for St. Jude Children’s Research Hospital. I don’t want people to feel compelled to do this or that, but rather to donate in a way that requires little resources from them. To me, St. Jude represents hope for children. Family is the most important aspect of my life, and the thought of any child struggling to live a healthy life is one of the most agonizing thoughts. The hospital is an amazing organization, and I am proud to be able to partner with them.

How did your vast business experiences help prepare you when founding Closet Angels? What challenges did you face when launching the foundation?
All of my experience has been in starting and building companies so it feels natural to do this as a next step. The difference is that with the other businesses I was involved in, we had a certain amount of working capital, but with Closet Angels, that isn’t there. Thus, the resources are much more limited and because of that, the growth rate will not be comparable to the other two companies.

In terms of challenges, I think people don’t always understand why they would donate their clothes to Closet Angels when they could sell them for a profit. They may not understand that, generally speaking, the financial benefit of donating rather than selling your clothing (and only receiving a portion) is actually stronger. That seems to be the question that friends ask, so I assume others think along the same lines. If you could personally gain more from donating (let’s not forget the most important aspect, which is helping children), then why would you do anything else?

How would you like to see Closet Angels grow over the next few years?
I would love to continue raising awareness and to grow year over year. Ideally, we would like to become one of the largest contributors to St. Jude Children’s Research Hospital, but that is going to take time!

Tell us about your transition from Groupon to starting your own company, Closet Angels. What have been some of the biggest adjustments?
Well, it has been an adjustment! I would say the largest adjustment at first was time-management. I am not accustomed to working from home all of the time, so getting into a rhythm of working efficiently without a group of people around me has been the hardest part, thus far.

Take us through a “typical” day at your office, if you have one. 
That’s a tough one as well. I spend a lot of time on e-mail and the phone. First thing in the morning, I generally spend a couple of hours on e-mail and try to not schedule any calls or meetings so I can focus, uninterrupted. Then, I usually have meetings for a few hours, then back to e-mails, and at the end of the day (sometimes late into the night), I look at the books—housekeeping type of stuff—Social Media, and I’ll brainstorm ideas for growth.

How do you balance your personal and professional life?
Ha! I have a mind that always wants to do more. I’m thinking of new ideas every day, so it is very hard for me to find that balance because watching television or reading a book doesn’t feel productive. The biggest grounding factor in my life is my dog, Coco, who just wants me around all of the time.

What is the most important lesson you’ve learned personally?
“It is your life; live it the way you want to live it.” It is a daily struggle for me to remember that and to do things that make me happy versus what others want me to do or expect me to do.

What is your career highlight, thus far?
That’s a tough one. I feel like I have done so much in a short period of time. If I had to pick one highlight, it would be talking with Oprah. I had grown up watching and admiring her, and the opportunity to work with her and her team, as well as being on her final season’s “Favorite Things” show is one of those moments in life that I will never forget. I felt like I was really doing something when that happened.

What advice would you give your 23 year-old-self?
Everything will be fine. Roll with the punches and have some fun!