Yesterday, I was the #1 sales rep. Today, I no longer have a job in sales.

Stephen Gladney
Salesloft Engineering
5 min readFeb 7, 2018
Image credit: Creativeart — Freepik.com

Last week was the end of our 2017 fiscal year. In a few weeks, I’ll be given an award for the top producing rep of 2017 for the commercial team. As of today, I no longer have a job in sales. So, what happened?

You have to go back almost 20 years. When I was 14, I got my hands on a copy of Visual Basic and taught myself how to code. I loved it. While other kids were outside playing sports, I was in front of a computer, writing programs. I wrote tons of them. I did it every day, from the moment I woke up until I went to bed. At school, instead of paying attention during class, I wrote games on my TI-83 calculator. I loved building things and watching them work. It’s still one of the greatest feelings to this day.

Then in high school, my attention shifted to cars, girls, and an emerging social life and I began to slowly lose the hobby. When it came time to go to college, I chose a well-known university simply because it was where you were supposed to go. I chose to major in marketing because I liked advertising and felt there was an opportunity to be creative in that field. It also seemed much easier than something like finance or accounting. Looking back with a sense of honesty, all of these choices were due to a lack of ambition and because they were simply the easy option at the time.

After college, and a very short stint in the music industry, I found a job with a publishing company selling advertising. I didn’t have a particular interest in sales, but it seemed like a good way to get into the industry. I was the only rep in my training class to not close a deal during our first month. I started searching for the next upcoming career fair because I was sure I was going to be fired. A year later, I was one of the top reps in the Atlanta office. So it turned out, I was pretty good at sales.

Two years later, I got the chance to work at a startup, called Scoutmob — a hip mobile app with an amazing brand that advertised local businesses to consumers. I would sell the advertising. They were literally running the company out of a loft apartment at the time. It was like something out of a movie. I had never been more excited about a new job in my life.

I excelled there and was often recognized as a top performer on the sales team. I was even promoted to my first outside sales job. One problem though. I began to envy the product and dev teams. I loved talking to the engineers about what they were working on and theorizing ideas with the founders about what we could do to enhance the product. It reminded me of my childhood hobby. I started to wish I had followed that passion in my career because it resonated with me on a much deeper level. And now, seven years into a sales career, my path was set in stone. I was a salesman. I certainly didn’t hate sales. I was good at it, which also meant that it paid well. I figured as long as I could work in sales in the “tech” world, I’d be happy.

When I interviewed with SalesLoft in 2015, I had zero software sales experience. Luckily, the person in charge of hiring me knew a former leader I worked under at Scoutmob who told him that I was “smart and could figure it out.” He decided to give me a shot. I remember he told me that I was going to be “his unicorn.”

SaleLoft CEO, Kyle Porter and COO, Rob Forman highlighting me at our weekly All-hands as a SalesLoft Star

I’ve done very well. A lot of that is due to the incredible sales leadership here. However, just like before, I’ve continued to envy the product team and engineers. In our old office, we had a meeting room called “the fishbowl.” The name came from the fact that all of the walls were glass and thus you could see into the room. I’d walk by the fishbowl often and see the product team inside white-boarding new product ideas. I wanted to be in that room so badly. My favorite part of the entire week was (and still is) the Product Update session at our all-hands meeting where the product managers and engineers demo upcoming features. I finally realized that I had this deeper calling to build things and I had to find a way to get into that side of the company.

I saw various people at SalesLoft make the move to Product from other departments and for the first time, I started to feel like I had a real chance to make the career change I had dreamed about for years.

I cannot even begin to express how thankful I am that I work at an organization where this is possible. Our founders often talk about their desire for opportunities to change the lives of their employees. This is one of those opportunities.

For the next year, I would drop hints to our Head of Product whenever I could. In every interaction, we would exchange jokes about me joining the team. I decided to show him that I was serious and asked if I could attend a product meeting, simply as a fly on the wall. I started asking engineers, product managers, and even our COO out to lunch. I told each of them about my secret passion and asked if it was possible for someone who’d only ever worked in sales to switch to a career in Product. I asked if they believed I would be capable of doing the job. Their support was unanimous.

During my lunch meeting with our COO, he gave me a book to read called Remarkable. It talks about working with purpose. I realized that I could continue being a sales rep, and I’d continue to be successful. I’d also make a hell of a lot more money. But it would be a job. Building software is a passion and something that connects with me on a deeper level. I’m not religious but dare I say, it speaks to my soul. Building software, for me, is working with purpose.

Several weeks later, the Head of Product sent me an email. He had an opening and he wanted to know how serious my interest in Product was. I sat there in disbelief. It was happening.

Today is now my first day as a Product Owner at SalesLoft. It’s also the first day of a new chapter of my career and my life and the first step in a much larger journey. I’m not really sure what the final destination will be, but for the first time in a long time, I’m excited about the future.

If you’re in a situation similar to mine, I hope this gives you the courage to take the leap, or even the first step, towards the career you truly want. Maybe you just need a little push. Well, here I am, saying to you…

Do it.

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