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Women in Business Q&A: Jayna Cooke, CEO & Partner, EVENTup

02/14/2015 06:46 am ET | Updated Apr 16, 2015

Jayna Cooke, CEO and Partner at EVENTup, is distinguished as being one of the most successful sales and business development professionals in technology startups over the past decade. Growth hacking and "just getting it done" are her specialties. As the Vice President of Business Development at Groupon, Jayna was integral in executing the company's early sales and partnership strategies. She helped launch various national and local sales strategies and successfully closed the two largest deals to date with national retailers Gap and Nordstrom. She was responsible for creating 25% of entire company revenue in 2009, and 10% of Gross Revenue for 2010. Prior to that, Jayna, started her career in sales at Echo Global Logistics (ECHS), where she held numerous roles including being the top sales executive such as Sales Trainer and Regional Manager. Jayna has also started her own foundation, "Closet Angels", has invested in several successful Chicago startups including Bucketfeet and Protein Bar, and sits on the board of several others.

How has your life experience made you the leader you are today?
Growing up in a large family, there was never a dull moment. I had lots of siblings so I quickly learned that if I didn't speak up, then I was not going to be heard. One of my favorite quotes my mother use to say was 'a closed mouth does not get fed' and that has stuck with me throughout my professional career, For anyone running a company - especially one as fast growing as EVENTup - it is important to always speak up.

How has your previous employment experience aided your tenure at EVENTup?
It all has been a perfect storm! I have been working since I was 13 years old. During my first job out of college I managed five 50-year employees so gaining respect and trust was hard at the beginning. However, I worked hard, was respectful and was able to turn a down business into a thriving business. This first experience with gave me the confidence I needed for the future, especially for managing employees.

Shortly after college I met my current business partner and mentor, Brad Keywell, who asked me what I wanted to do. I simply replied 'You're successful. I want to do what you do.' Brad encouraged me to start in sales and we started with Echo Global Logistics (ECHS). I quickly realized that while I didn't have a ton of sales experience, I was fast and I could prioritize well. These qualities - combined with my work ethic - led me to be the first into the office and one of the last to leave everyday. Within two months, I was training the new employees and then moved into management.

My experience at Echo helped me realize not only what I was good at (e.g., the ability to be persistent, move fast and execute even faster), but also what I was really interested in for the future. This realization brought me to The Point, which soon evolved into Groupon (GRPN). At Groupon I was in charge of the company's business development efforts, which is what I really loved. I helped define markets to launch, wrote sales documents and strategies, worked on larger partnerships - all while building and maintaining the company's largest book of business. I was also able to apply a lot of the sales knowledge I had gained from Echo to my experience at Groupon which helped me close deals with Nordstrom and Gap and get us included in Oprah's coveted 'Favorite Things' show.

The wide variety of experience - from calling truck drivers up to CEO's of billion dollar companies - gave me the skills I need to make EVENTup work. I still make cold calls everyday.

What have the highlights and challenges been during your tenure at EVENTup?
That is a tough question. I think anyone starting a business has days where you think you are going to rule the world and equally as many days where you think you are the dirt on the sidewalk. Two recent highlights for me were great testimonials from Google and Apple (two of my personally most respected companies) raving about our services and how much it has helped them. The biggest challenge for me has been hiring. We are a fast growing company, but it takes time to find the right people and to train them. We have had amazing growth month over month and have hit all our targets, but I want to grow faster. It is hard for me to be patient because I see the path and want to move faster all the time!

What advice can you offer to women who want a career in your industry?
Dive in. Sheryl Sandberg coined the phrase 'Lean In', but if it were up to me the industry catchphrase would be 'Dive In.' Spend some time evaluating what you are going to do and what your goals are and do a small test on your own. If it works, go for it. Even if you fail you will know what not to do for the next time. You cannot be afraid to jump (or dive) in!

What is the most important lesson you've learned in your career to date?
One of my favorite quotes is from Steve Jobs... 'Stay Foolish, Stay Hungry.' You have to be both of those in order to succeed to any great level in my opinion. Don't always listen to what other people tell you as they are almost always going to tell you what won't work. Try it yourself.

How do you maintain a work/life balance?
To be honest, this is really a challenge for me. I have a small, tightknit group of amazing friends who have been with me throughout most of my life and my professional career. They understand the ebbs and flows of running a business and support me regardless of my crazy schedule.

What do you think is the biggest issue for women in the workplace?
I think it goes back to 'diving in.' I have managed hundreds of people throughout my career and 9 times out of 10 men are the ones who ASK. Whether it is more money, more responsibility - whoever is asking is going to be the person that gets it. Long story short - ASK.

How has mentorship made a difference in your professional and personal life?
I believe it's invaluable to have someone to look up to and be a good role model to follow - both in life and in business. Mentorship is not just a weekly meeting, it is an ongoing process/relationship that allows you to ask questions, bounce ideas around and get feedback. And you don't have to have just ONE mentor! I have a few people that I really count on and look up to that teach me different things in different situations.

Which other female leaders do you admire and why?
Oprah is arguably the most notable. I feel like she always followed what she wanted to do regardless of what anyone said or what anyone else wanted.

Another leader I admire is Hilary Clinton. I do not necessarily agree with all of her political views, but she has navigated her way through a male-dominated world extraordinarily well. Navigating through life in general is really tough, and being able to do it as well as she has is commendable.

What do you want EVENTup to accomplish in the next year?
While we are already the largest online marketplace for event space and venues across the US with over 10,000 venues, we have really just begin to scratch the surface. We are developing some really revolutionary technology right now that will have a dramatic impact on our roadmap and I believe, will change the way companies and people plan and book events.