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).
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I used to work at a call center. We sold financial services for a regional company that’s no longer around. The company did a lot of radio and television advertising, so much of our business came through inbound calls after people saw our ads and called into the 800-number. 

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Weekends were slow, but we still needed coverage, so we would essentially rotate employees who had to work weekends. It would work out that every rep would work one weekend day a month, either Saturday or Sunday. There were barely any employees working on those weekend days, usually no manager, and it was super casual. We all wore whatever we wanted etc. 

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One day, I was on a weekend shift with two other guys. It happened to be two of the funnier people I worked with, so we were kind of having a great time. We ordered a pizza and kind of hung out talking in between calls. 

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It was my turn in the call queue, and I got a call from a guy who seemed like a great prospect. He seemed normal (sometimes we got some very strange people calling because they saw our number), was qualified, and seemed like he would be easy to deal with. 

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Well, as I’m going through the application, one of my coworkers, who was a big guy, stretched. And as he stretched, he let out this primal scream at the top of his lungs. I don’t know if he forgot that I was on the phone or what, but he sounded like he had just been attacked or something like that. So loud. 

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All of a sudden, my caller stopped talking. Then he asked me what that was. I tried to play it off like it was nothing and everything was fine, but he got super uncomfortable. Then he asked if I was sure everything was okay, and I said yes. But he only talked to me for another minute or so before saying he forgot he had an appointment and that he had to go. I tried calling him back a bunch of times later that day and the following week, but he never answered my calls. Quiet down when people are selling! 

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Anonymous             Location Withheld 

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This happened less than six months ago, and is my biggest Sales Fail of all time. I work for a digital agency. We build high-end websites and handle branding, and don’t do any contracts under 50k, though most of our deals start at 100k. It’s a great job – I like what I sell and usually like my clientele, which are high-growth companies and recently funded startups.

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The Fail happened with a company that had just raised almost 40m in funding. I had been talking to their head of marketing for close to a year. I originally connected with her when they raised their first round, which was 5m. The marketing team were keen to get moving, but it was difficult to get buy-in from executives, who were (rightly) looking to watch their spending.

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But around the time they were raising this next round of funding, the head of marketing started getting more serious about moving forward. We had multiple pitch meetings, and changed the scope of work a bunch. At the end of it, they were going to commit to a $140k contract. It was a really great deal. She gave me the verbal, and we sent over the paperwork the same week they announced the new funding round. 

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I have to admit, I was already celebrating the deal. There was a watch I had been wanting for a while (Omega Seamaster) and I literally ordered it online as soon as she gave the verbal. I’m sure you know what happened next. I didn’t hear from her for a few days, then I got an email from her head of growth who let me know that she had been let go, and they were going to hold off on any new agreements until they brought in their new head of marketing, which never actually happened. The deal was dead. It was absolutely brutal. But a good reminder to never count your deals until they sign (or maybe until they pay). Oh, and I still ended up buying the watch. 

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Anonymous             Location Withheld 

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I had just started a new role as a sales rep responsible for building a reseller network for a new product, and was in an introductory meeting with a potentially significant new reseller.  

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Everything was going very well and they were definitely interested in exploring a partnership, both because of the product fit and also because they liked our approach of only selling through an exclusive, invite only channel.  

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I had finished up my initial pitch and one of the attendees had to depart the meeting and requested I leave him with my business card, which I dutifully provided from the stash I had brought.  Upon taking possession of said card the gentleman's demeanor turned from warm and enthused to rather confused. 

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I realized (too late) that unfortunately the first card I retrieved happened to be a business card from one of his direct competitors, to whom I had pitched the day before. This took a bit of the gloss off my appeal to exclusivity and I've been very deliberate about not mixing business cards ever since...

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Anonymous             New Zealand