Sales Fails: "I left a great-paying sales job for a startup that failed within two months"

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 is more of a career fail than a sales fail, but when I read these things, I always think about something really dumb I did in my late 20’s. I was working this pretty amazing sales job doing financial sales at the time. It wasn’t perfect by any means, but compensation-wise, it was great. 

We were an all-inbound call center, and our company advertised really heavily on the radio. Normally, an inbound-only call center would have a crappy comp plan since there’s no real prospecting involved, but this company paid well. You could break six-figures basically by showing up and going through the motions. It was a stressful sale, but like I said, if you showed up and answered the phone and weren’t completely incompetent, you could get paid. 

At that point, I was making more money than I’d ever made before. Month after month. Honestly, it felt like a dream come true since I grew up in a working-class environment. But I somehow managed to screw it all up. 

My sales manager at the time got into a pretty heated dispute with the general manager. He (my sales manager) felt like he should have been compensated for a particular deal, which he never got paid out for, since he was a producing manager. The general manager basically told him, “No one is chaining you to your desk,” basically saying if you don’t like it, then leave, and my sales manager took him up on it and left. 

The company he went to was a startup in the same exact space. After he went, he recruited me and another guy that worked with us, and we both made the jump. Well, it turned out to be a ridiculously dumb move on my part. It was just the three of us in a tiny office, with absolutely no leads whatsoever. After a few weeks, the sales manager used his AMEX to buy us 10k worth of leads from some outbound call service, but we burned through those in an afternoon. 

Long story short, after about a month, I ended up quitting and moving back in with my parents (lol seriously) and the company closed down a few months after that. The second guy that came with us went back to the company we both left, but I never got an invite back. The sales manager became a realtor, and is pretty successful from what I understand. I’m doing fine now, but I definitely walked away from hundreds of thousands of dollars in income. The grass isn’t always greener on the other side. 

Anonymous, 37           New Jersey       

“This didn’t happen to me, but I worked for a (car) dealership when it happened. One of my coworkers sold a truck to a younger guy who said he’d be paying for it in all cash, but he needed to go home and get the money. My coworker (the salesman) was skeptical and thought the guy wouldn’t come back, but a few hours later, he got dropped off at the dealership with a huge wad of cash. I don’t remember exactly how much the truck cost but it was around ten grand or just under (this was a long time ago).

Anyway, the guy pays for the truck, and I see my coworker and the GM in their office looking at the money, and all of it was in these older bills that had been discontinued. But the money was real, and a sale was a sale, so we did the paperwork and the guy left in his new pickup. 

A few weeks later, the cops show up at the dealership and ask to talk to the manager. It turned out that this guy (the customer) had stolen a bunch of money from some old man who he had done some housework for. Apparently, the old man didn’t trust banks and kept a bunch of cash hidden throughout his house. My coworker and manager had to appear as witnesses at this guy’s trial, and from what I remember, he got sent to prison for a long time. Not sure what ever happened to the truck, but it’s one of the crazier stories from my time in sales.” 

Anonymous         Location withheld        

“This actually happened to me pretty recently. I’m an AE for a software company in restaurant tech, and I got a referral from one of my customers to someone they know at another restaurant, which is actually pretty rare (for me anyway). I was pumped to get the referral and reached out to the new prospect right away. 

But here’s the deal: this guy (the new prospect) is one of those people whose last name sounds like a first name, so it’s pretty confusing. For example (and this is one I just made up since I can’t reveal his identity), pretend that his name was Robert John. Confusing, right?

Anyway, when I first reached out, I got his first name right, because I was reading it off the other email. But after he responded and we started talking, I was too quick to type up my responses (what can I say, I type fast) and accidentally kept calling him by his last name. So, using the example above, I was basically starting my emails with “Hey John” instead of “Hey Robert.” 

This went on like this for a few emails, but I noticed he kept taking longer and longer to respond. Finally, on the third response, he said: “By the way, my first name is X, and X is my last name.” I apologized profusely, but he took forever to respond and eventually just stopped getting back to me. Can’t tell if he didn’t like our pricing/product or if it was the name thing, but either way, I’m sure it didn’t help.” 

Anonymous, 35          New York              

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