The Good, The Bad & The Downright Ugly of Sales


When I was 10 years old, my mom came home from work one day and noticed that all the flowers around our house had disappeared. There I was, in the front yard, with a pile of the flowers she worked so hard to plant.

“Jayna, what are you doing!!?” she said.

“Mom, I’m selling flowers!”

“Honey, you can’t do that.”

“But Mom, I made $5.”

“Jayna, you still can’t do that.”

To me, “No” just meant that I had to find another way to sell. So next week, when my mom returned home from work, I wasn’t selling flowers – I was selling the potting soil that once held all the flowers.

To become effective salespeople and entrepreneurs, I believe we have to rip a lot of flowers out of the ground. We have to be told “no” and then go get our hands dirty again and again and again. Selling is not an algorithm that you can program into a machine. It takes 10,000 hours, not 10,000 lines of code. There are different ways to spend those 10,000 hours, and my goal here in Forbes is to offer ideas that will help you use your time in the best way possible.

Sales is an art, and by examining the good, the bad and the downright ugly of sales, we can learn to hone it. Between pure people skills and all the automation, lead generation technology and hard metrics that define modern sales, there is a sweet spot. My mission is to guide you toward this “Golden Mean of Sales” – a nirvana-like state where we can be efficient and be human.

So why am I doing this? Besides my childhood experiences selling flowers and dirt to strangers, what makes my sales ideas worth considering?

My understanding of the “Golden Mean of Sales” comes from 12 years of field experience. I started my career as a district sales manager for Neiman Marcus in Michigan, and eventually joined Echo Global Logistics ECHO -2.48%, now a publicly traded $1.8 billion transportation management firm that uses technology to make shipping uncomplicated.

When I started at Echo, there were about 20 people. With so few veterans around, I got hands-on with enterprise sales, profit/loss management, hiring, training and running a business in general. I became the company’s top performer in terms of gross revenue and margin. Apparently, I still hold the all-time record for largest revenue and gross profit achieved in one month and one day.

In 2008, I joined Groupon GRPN +6.64% and became the company’s top sales performer worldwide. I closed deals with Gap GPS +0.72% and Nordstrom JWN -1.23%, Groupon’s two largest deals to date. I was there for more than four  years and felt ready for a new challenge.

Soon after Groupon went public in 2011, I left to launch Closet Angels, a non-profit that sells donated designer goods and gives the proceeds to St. Jude Children’s Research Hospital. Nostalgic for the competition and fun of sales, I joined EVENTup in 2014 as a partner and CEO. Today, I help companies find event venues across the U.S., and I help venue owners publicize their event spaces.

The event space is an archaic, fragmented, $600 billion market ripe for disruption. In tech language, you might call EVENTup a “two-way event marketplace” or something fancy like that. As you’ll learn in my next blog post, about the art of cold calling, that is not the way to pitch a company if you want to earn any business.

In other upcoming blog posts, I will write about sales tactics; real-life examples of good, bad and ugly pitches; thoughts on building and managing sales teams; and ways to conquer the myriad of challenges that confront salespeople and entrepreneurs.

Maybe you’re an entrepreneur who has a product or service but is trying to figure out how to sell it; maybe you’re in sales because you’re passionate about what you sell. Maybe you love competition. It doesn’t matter. There is no wrong reason for being great at what you do. We’re going to focus on the art of sales because there is something inherently rewarding about cultivating an art form. The grass will always seem greener somewhere else unless you strive to be awesome here and now, in whatever you do.

Join me regularly for the good, the bad and the downright ugly of sales. Let’s rip out some flowers.

This can also be found on the Forbes blog here.


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