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).
This one is from the pre-pandemic era, when we were all still in the office. I was interviewing for an Account Executive job at a funded startup. I cleared the first two interviews over the phone and got asked to come into the office for a final interview with the CEO, who approved all hires.
The office had typical startup vibes (drinks on tap, ping-pong table, etc.) and I could tell the VP of sales really wanted me to join. After a tour, he told me to go into the CEOs office. I knocked on the door and heard the CEO yell for me to come in. I couldn't believe it, but the guy was riding a Peloton bike in his office. It was straight out of a movie. He was doing the power move of working out while taking a meeting. I was a bit taken aback, but the CEO just asked me 4 or 5 basic questions in between his labored breathing and said, "You ready to get on the rocketship?" I told him yes and he said, "Great, you're hired" while still riding the bike.
It was a huge red flag that I of course ignored. I ended up taking the job and less than a year later, I got laid off along with most of the sales team. The company went out of business.
Anonymous Location withheld
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I was in my early 20s when I got my first sales job working at a mattress store. Most of the sales staff were young and we would hang out and party sometimes after work. We had a house party until 4 AM and a few of us had to work the next day. One of the guys who partied a bit too hard ended up falling asleep on one of the display beds in the middle of the shift.
Our manager was out that day so I was technically in charge, but still a dumb kid, so I recruited one of the other sales reps and we started building a giant pillow fort around the guy who was sleeping. The fort got so high you couldn't even see that there was a person in there, except for his black Converse hanging out the bottom. We thought it was the funniest thing ever. Customers would walk by slowly just looking in bewilderment trying to figure out what was going on. We woke him up about an hour later. No mattresses were sold that day.
Anonymous Location withheld
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I work at a high end jewelry store. One day, this guy came in by himself on a pretty slow day. He said he was looking for diamond earrings, but he was dodging questions when I tried to build rapport or ask who he was buying them for. I helped him find a really nice pair, and he looked at them for a few minutes and decided he would buy them. He made the decision so quickly and didn't flinch at the price, so I decided to try to upsell him on a necklace that was a matching set with the earrings. He wouldn't bite and said he just wanted the earrings.
I didn't think much of it again until he came in about a month later with a beautiful woman. Neither of them were wearing wedding rings, but I assumed this was the girlfriend that he had bought the earrings for. I greeted them both and asked the guy if he had changed his mind and wanted to buy the necklace to go with the earrings. The woman he was with wasn't really paying attention, but the guy looked at me right in the eyes with a look of fear and I immediately knew I made a mistake — this was a different woman than whoever he had bought the earrings for last time. I changed the subject quickly and started complimenting the woman on some of the pieces she was wearing. The guy ended up buying a pair of earrings for this woman and they both left happy. Luckily, I didn't cause any problems for the guy or lose my commission. Remember: never assume.
Anonymous Location withheld
