Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).
I have worked in tech sales for close to a decade. Very early in my career, I was working for a small startup. This was the job I used to break into tech sales, and I probably only got hired because the company was so small. There were a total of six employees and our engineering team was based in Estonia.
The sales team consisted of me, another Account Executive, and the VP of Sales. That was it. Just the three of us. All day long, we called prospective customers from what was basically the phone book — we sold software to motels, so we basically just called motels all day. Sometimes, we would get inbound leads, but it was about 80% outbound.
One day, I got us a meeting with a pretty big (for us) motel group in North Carolina. The plan was for my sales manager to run the meeting, which I was fine with. We got on a conference call (video calls weren’t as big as they are now), and I introduced our team, and the hotel group partner introduced his side — there were four of them: the owner and three managers.
My VP of sales gave his opening spiel. Then (as planned) he asked the owner a question. The owner gave a very short answer, and I think my VP got nervous, because he just started talking and talking and talking. He talked for like five minutes straight. Then, when he paused again, the other side didn’t say anything, so he kept on talking. I swear, he talked for a half hour straight, just because he was afraid of encountering any silence.
It was so ridiculous that I wanted to motion for him to zip his lips, but I also didn’t want to offend him since he was my boss and up to that point had taught me everything I knew about tech sales. In any case, he kept talking until they finally cut him off and told him they had a hard stop. They were polite but I think we came off as complete amateurs. There was no deal.
Anonymous Location withheld
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I used to work as a rental agent in a big city. Our company owned a bunch of apartment buildings, and we were also contracted to show other properties. Collectively, we managed thousands of units. It was a pretty decent job, especially since I was only a few years out of college.
One day, I was showing a young professional couple one of our higher end apartments. It was a top floor unit in a five-unit building. It was one of those old brick New England buildings that had been converted into separate apartments. Since traffic was bad, we met at my office and we all drove over together in my car.
The second we stepped foot in the lobby, I heard a woman screaming. Then I heard another woman screaming back at her. I thought it would stop after a few seconds, but it kept going and getting worse. The two tenants on the second floor were in a drag-out fight, screaming at the absolute top of their lungs, calling each other awful names. One of them started crying, but she kept on screaming.
At first I tried to ignore it, and pretend like nothing was happening, but that didn’t work. We walked around the unit awkwardly as the two of them continued their reign of terror downstairs. Finally, I asked my clients to excuse me and went downstairs and knocked on their door. One of the two young women answered, and apologized. I could see the second woman glaring at me from the kitchen behind her. They were quiet for a few minutes but then their voices started rising again and then they were back at it.
My clients were awkward about it at first, but when we got back in the car, they kind of lightened up. In any case, they did not take the unit, even though it was perfect. Obviously, they were worried that they would be disturbed by the lunatics living on the second floor. As far as those two, one of them moved out a month later. She subleased her portion of the lease to somebody else.
Anonymous Location withheld
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I used to work for a mortgage company that did a lot of advertising on the radio as well as with flashy digital signs. We were a regional player. The company did really well for a number of years. The owner was known for being a colorful personality. He made a ton of money over the years though.
Back in 2011, things were still recovering from the great recession. The company wasn’t doing super well and management was brainstorming ways to bring in new business. They wanted to revamp their advertising messages and come up with new ways to entice people to call in to do refinances, since purchase volume was way down.
At the time, even though I was a mortgage broker, I wanted to get into marketing. I wanted a more steady paycheck and wanted to be more creative in my day-to-day life. So when these discussions were happening, I had a great idea: I would go home and put together an entire ad campaign for the company to give to the agency they were using to write and perform the radio ads.
It took me about a week to put everything together. I thought my campaign was good and pretty funny. It talked about all the things you could buy if you saved money on your mortgage payment by refinancing, but it was funny/useless things (ex: a $1,000 hat etc.). Anyway, I put everything together in a nice laminated and bound folder and gave it to my manager who looked at it with a strange expression and promised to pass it along to the owner.
Can you guess what they did? They FIRED me. Seriously. The week after, my manager asked me into his office and told me they were letting me go because I wasn’t focused enough on my work. I couldn’t believe it. I was hitting my numbers while all this was happening, I just wanted to try something else. In retrospect, it was a blessing in disguise. Ten years later the company fell apart. I tried marketing since then, but went back into sales because the money is just so good. Still can’t believe they fired me though!
Anonymous Location withheld
