Jayna Cooke on the importance of resilience

Jayna Cooke is CEO and Partner at EVENTup, an online marketplace for finding venues and event spaces across the US. Despite her young age, Jayna is distinguished as being one of the most successful sales and business development professionals in technology startups over the past decade. Her career started in retail sales, setting the foundation for what would be an extremely fruitful career. She went on to be the Vice President of Business Development at Groupon, playing an integral role in executing the company's early sales and partnership strategies. Jayna is ambitious and driven with a passion for shaking up industries.

What did you want to be when you grew up?
I feel like it changed every week. I don't know if I had a clear-cut idea of what I wanted to be but I do remember wanting to be a veterinarian at some stage. 

Who would you invite to your dream dinner party?
My grandma, my mom, my best friend and my boyfriend. Then I would invite Bruno Mars, Oprah Winfrey, Jimmy Fallon, Tina Fey and Emily Blunt.

What single book had the greatest impact on you?
Unfortunately, I'm not a big reader at all but The Secret by Rhonda Byrne changed the way I approach life and helped me address optimism from a different angle. It had a very positive influence on my life and happiness.

When do you go to bed and when do you get up?
I try to be in bed by 10pm, which means I'm not asleep till 11pm. I have a long period of lying there. I usually get up between 5:30am and 6:00am.

What is your favorite time of the working week?
By Wednesday and Thursday I always feel I have made it over the hump so I'm usually less stressed on those days. I love doing work at 8 or 9pm at night because there aren’t 500 things to address. It's my time when I can do what I want without the interruptions.

Can you briefly explain your career path to date?
It's been a fun one. I started working when I was 13 but perhaps I should start when I graduated because I did about 50 things up to that point. When I first graduated from college I was a DSM, which is basically a mini-buyer for St Johns Knits at Neiman Marcus in Michigan. Every quarter I would go and select the stock that I believed would sell in our store. I managed a team of five women all over the age of 50 who had all been there for a minimum of 10 years. I was 22 years old and stayed for about 2 years. I learned a lot about buying and selling, consumer wants and needs and marketplace trends. It was a great foundation.

Then I met my current business partner and worked for Echo, a freight management company, in it's very early days. It meant I learnt how to do many different things associated with sales like training the sales team, creating sales materials and enterprise sales. I was a team manager and then became a regional manager. The company had very fast growth and went public really quickly.

The second move with my business partner was to The Point, which eventually turned into Groupon. I was VP of Business Development. I got to work on big national deals deciding which markets we should expand into and what our business strategy was for growth, sales call and sales cycles. 

The Point was a website where you would gather together multiple people based on a tipping point. So The Point would go to someone like BP oil and propose an agreement for change based on a certain number of people signing a petition. We were making no money, so the two founders came up with Groupon based of the same model. I was there on day one of Groupon until it went public which was a little over 4 years.

When I left Groupon I spent a year establishing a not-for-profit called Closet Angels. The premise being that designers donate their clothing to us, we re-sell it and all profits go to St Jude Children's Research Hospital. It still exists today and runs on it's own now. 

My latest venture is called EVENTup, which my business partners and I took over in March 2014. It's an online marketplace where you can find any event or venue space. If you want a rooftop in Manhattan or you're looking for something in Chinatown, whatever it is, you can find it on there.

What is the biggest obstacle you’ve overcome, as it relates to your industry?
There are a million challenges with any industry and with any business. In my opinion tech is a weird bubble unlike any other industry. It's essentially just a race for who can grow the fastest and execute the quickest.

Something that's hard for me and it continues to be a challenge, is spending money. You have to spend money because you have to be able to grow fast and fast and fast. That's really outside of my comfort zone. I'm a risk taker but I'm much more calculated. For instance, I know when I bring an employee on I'm paying out the door for them for at least 3 months minimum.

I just don't like to spend money. I recognize it's a challenge for me and I don't want it to hold the company back by any means. I'm much more careful than 90% of my counterparts out there. 

What motivates you?
My mom always says that I came out kicking and screaming! I don't know what it is but I love to work. I'm a worker bee. I love lists of challenges, crossing them off and moving onto the next. It's kind of a blessing and a curse because there's always something more that I want. So when I have a success, the hurrah lasts for half a day and then I'm onto the next. I'm extremely self-motivated. I want to change industries and the way people think about and access things. I'm constantly trying to reinvent how industries work. 

What advice would you give to someone at the start of his or her career?
My number one advice would be to follow what makes you happy regardless of what anybody says or tells you to do. Along the way I've definitely gotten lost but by honing in on what makes me happy and understanding how to continually be happy, is vital.

What do you consider your greatest achievement?
I am really proud of a partnership we did with Oprah when I was at Groupon. It was with Kiva.org, which provides micro-loans to third world countries. It was about three or four years ago and we raised over a million dollars. That was one of my moments where things came full circle. One of the things I've always admired about Oprah is her philanthropic nature. She has always given back and honed into those charity roots. Bringing her together with Kiva was something really special.

What do you believe has been the key to your success?
It goes back to one or two things. 

1. Resourcefulness. You just have to figure out how to get things done in any way, shape or form and never ever give up. If you tell me I can't do something I will definitely find a way.

2. Resilience. Not just in work but in life. It's got to be one of the main characteristics to happiness and longevity in life.

What is the most important lesson life has taught you?
Each person is different and what makes them happy is so varied. I based my notions of happiness on what other people thought would make me happy, then I was lucky enough to achieve some of those things but it didn't do anything to fulfill me.

Work makes me happy. I love to help people, but I also love my friends and family. I have to ensure that I always prioritize that and understand that when I'm with my friends and family, they should be my focus.

What do you believe are the personality traits of great leaders?
Resilience is huge. When I look at my business partner for example, who has had tremendous success, he's just very resilient. 

Kindness over time. Once you've had a significant run at a career, really give it time. Be nice to the people around you because you never know when you're going to need that bridge. I see it too often that people think of people as casualties or a commodity. In some ways people are a commodity but they're also humans and you need to be sensitive and respectful of that.

What do you believe to be the secret to rising up to the top?
I think you need to really believe it. You need to whole-heartedly believe what you want to do. Everyone has a different version of rising to the top, really honing in on what your version of it is, is vital. My rising to the top is that I can create a new range of successful businesses, not just one. So I feel right now that EVENTup is amazing and it's a chapter in my life. In 20 years I'll be involved in it but not in the same capacity that I am now. 

Everybody needs to think about it in their own way and really think about it. Think about it every night before you go to bed, what is you end goal? Where do you want to be? Where do you want your company to be? I spend probably an hour every night thinking about it.

Who do you turn to when the going gets tough?
It depends on the situation but my grandma, my best friend, my mom and my boyfriend are the first line of defense.

If it's a business questions that's completely over my head I would turn to my business partner, Brad. 

What's next?
Right now I am full on focused, head down in EVENTup. I'm trying to develop the business and we need more tech resources to build out the product. What we have is an amazing product, we have 15,000 venues online, nation-wide already but we need to develop the product so it's more user-friendly and more of a real marketplace than a platform.


As told to Caroline Hugall over Skype on Friday 17th April 2015. Jayna is based in Chicago.