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A long time ago, back when selling software was still niche, I sold software to mortgage companies and banks. We were definitely an established company, but we had a competitor that had a good hold on the market, so we weren’t the “obvious” choice or anything like that.
I was in Chicago, and had set up a meeting with three executives from a big regional bank who were unhappy with their in-house solution. My manager was supposed to come to the meeting with me but his wife was sick and he couldn’t make it, so we decided I’d take the meeting alone.
The meeting was at a nice steak restaurant, and I was looking forward to having a nice dinner and closing what would be my biggest deal thus far. Well, the hotel I was staying at was only a few blocks from the restaurant, so I decided to walk over. I ironed my shirt, put on nice slacks and a jacket, checked my hair and headed out.
Mind you, the day had been perfectly clear. All day long, it was perfectly clear. But the moment I stepped outside, the clouds rolled in and it started absolutely pouring. One of those torrential rains that starts in an instant and comes down like crazy, soaking everything in its path.
By the time I got to the restaurant, I was completely soaked through. My jacket, my shirt, my pants, my shoes, soaked. It was brutal. The bankers looked at me like I had five heads. They didn’t make a single joke about it, just looked at me like I was insane or something.
The dinner was miserable. I was uncomfortable and just wanted to get back to the hotel and take a shower and change. The executives, meanwhile, talked mostly among themselves and we only spent maybe twenty minutes talking about business. I don’t think they took a guy who looked like he’d just jumped in a lake seriously. They thanked me for the meal and we all headed out. I didn’t close the deal, but got a pretty hilarious story out of it at least.
Anonymous Location withheld
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This is something that happened to me around this time last year. I work as a BDR at a sales tech company. So naturally, I spent a lot of time cold calling and sending cold emails. I did some research on an account I wanted to land that seemed like an ideal client. I sent a personalized email to the VP who I knew would be the final decision maker. I got an email back a day later from a mid-level manager at the company who said that the VP had forwarded the email to him and asked him to explore our solution. This isn't uncommon, I've actually closed a few deals by turning the middle manager into my champion, so I was excited. I set up the call for later in the week.
The meeting time came and the guy was a no show. I waited 5 minutes and sent him an email politely letting him know I was in the meeting link. No answer. After another 5 minutes later I decided to call the phone number in his email signature. It was the last week of the month and I needed the deal. The guy answered the phone, sounding confused. I could tell by his voice that I had woken him up (it was well into the afternoon). I told the guy we could reschedule, but he frantically insisted now was still a good time and that he'd be on the Zoom in 5 minutes.
He joined the call all disheveled; he was wearing a baseball cap trying to hide his bedhead and had on an old sweatshirt. He looked like he was still dreaming about his pillow. I told him again that we could reschedule but he insisted he was ready and asked if we could get into the pitch. I went along and told him more about our company and solution, but when I asked him discovery questions he would reply with short answers that didn't help keep the conversation going. He kept looking at his phone, and it was clear that he just took the meeting so he could tell his boss that he had done it. At the end of the call, he asked me to send a follow-up with all the info we discussed as well as next steps. Not surprisingly I never heard from him again. Sales Fail!
Anonymous Location withheld
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This is maybe more of a Buying Fail than a Sales Fail, but it’s still pretty bad. Let’s set the scene. About six years ago I was employee number five at a small startup. I was basically the first hire who wasn’t on the founding team. Even though we had no revenue and technically no product to sell, I was brought in at a really nice salary to build out the (future) sales organization.
For me, it was a nice change of pace from the high-stress environment I came from, so part of the reason why I took the job was that I knew I’d have some “downtime” while they built out the product and got it ready to ship. It seemed like a good team and – this part is important – they raised almost six million dollars from one very rich investor, so I knew they had some runway.
This is where things get a bit hairy. Since there was nothing to sell, I was basically the jack-of-all trades with sales, partnerships, marketing, and PR. I didn’t know much about it but I’m a competent person so I wasn’t worried. At this same time, our funding announcement had gone out, so we had all these people coming out of the woodwork trying to sell us something or trying to get a job since they knew we were sitting on $5m in a not-so-happening city outside the coasts.
Well, one vendor was extremely aggressive. They wanted to put together an entire marketing and public relations plan for us for $15k. He called and emailed me and the founders so much that one of the founders finally told me to see what it was all about. I got on a call with this guy, and he had a really bare bones website but he explained that he was a small operation which is why his prices were so good. He also had a strange accent, but when I asked where he was from he swore up and down that he was born in NYC and still lived there.
I had a bad feeling about it, but he smooth-talked one of the founders and convinced him that this was a great deal and that he could show results almost right away. I voiced my opinion but they didn’t listen, and they signed a contract with this guy and wired him $10k out of the $15k. Well, can you guess what happened? That’s right! He completely disappeared and we never heard from him again. It was possibly the dumbest thing I’ve ever been a part of. On the bright side, I was the one who had warned everyone, and it bought me some good will. Unfortunately, four years later, the company ran out of money and was forced to close. Wonder why.
Anonymous Location withheld
