Jayna Cooke is CEO and founder of Chicago-based EVENTup, the largest online marketplace for event venues. (EVENTup was recently acquired by Gather.) Cooke was also former VP of business development (and one of the first employees) at Groupon, where she was the top global sales performer, responsible for the company’s two largest deals: with Nordstrom and Gap. Before that, she was the top seller at Echo Global Logistics.  In 2012, Cooke started Closet Angels, a 501.c.3 foundation that collects and sells designer clothes to benefit St. Jude’s Children’s Research Hospital.

We reached out to Cooke to discover the secret to her success and gain advice on ways to successfully sell a business.

In the right place at the right time

When Cooke joined Echo Global Logistics, she had the opportunity to wear a lot of different hats. Cooke started in sales and trained new hires. She also helped to create an enterprise sales division, managed teams, and had a lot of other duties. “I was lucky to be there in such a growth period and roughly four years after I joined, the company went public on the NYSE,” Cooke says. “It was such an exciting time and the company really needed individuals that could be resourceful and move forward as fast as possible.”

I was able to spread my wings.

Her next stop was at Groupon, where she was VP of Business Development. Groupon had the same founders as Echo, so they knew how much value Cooke could bring to the organization. “Again, I was very lucky in the sense that so early I was able to spread my wings and explore numerous incremental revenue opportunities.” Since business development included sales and partnership from a variety of sectors, she was able to work with Oprah, Gap, and Forbes, among other big brands. “My goal was to help grow the company as fast as possible — which we had great success at doing,” Cooke says. “We experienced a tremendous rate of growth and I was there through the transition to a public company.”

After she left Groupon, Cooke was exploring her options, and says the opportunity arose to take over EVENTup. “I partnered with Lightbank (the VC firm by the founders of Echo and Groupon) and we took over the company in 2014,” she says. “We grew EVENTup to great heights and were approached with an offer to sell our business early this year — we decided the timing was right so we made that happen.”

Advice for successfully selling your business

If you’re thinking about selling your business, Cooke offers the following tips:

1. Start looking for a buyer on day one

“Start by making a list of competitors and other companies within your space,” she says.  “Companies that are not direct competitors today — but have a similar customer base — are a great starting point because you never know their expansion plans.”

Cooke admits that might sound like a risky move. “You do not want to reveal your ‘secret sauce’ and have someone duplicate it,” she says. “However, it is worth a conversation and forging a relationship as once they decide to start offering a product similar to yours or expand into your space, you will be the first place they head for acquisition — which is often more cost effective than building from scratch.”

It’s important to maintain relationships.

Cooke says it’s also important to maintain these relationships. In fact, she says you should initiate contact with them at least once or twice a year.

2. Be ready

“It is easier to have a buyer approach you versus actively trying to sell your company,” Cooke explains. She says timing is critically important, so you should always plan ahead. “If a potential buyer reaches out with interest, hear them out right away, even if you are not quite ready to sell,” Cooke advises. Not only will you be able to gauge how serious they are, but you can also gauge their goals and motivation. And she says this will give you the opportunity to understand how serious the potential buyer might be and also understand their goals and what’s motivating their desire to buy.

3. Know what you want

Cooke says it’s unlikely that you’ll get everything you want. “However, having a written list of what is important to guide you along the process is extremely beneficial,” she explains. “The process is exhausting and exhilarating at the same time and decisions are generally made quickly so you need to be prepared to negotiate on exactly what you want and know exactly what you are willing to give.”

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