I work in the mortgage industry and have been doing it for a very long time. My best Sales Fails story happened about ten years ago when I was an LO (Loan Originator) for a big lender. I got a web lead for a married couple looking to do a home purchase and I prequalified them and they started shopping around together for a house.
They found a house they liked and got an accepted offer. We did all the paperwork, they did their inspections and everything else, and we were all set to close at the end of the month. It was a done deal and had gone really smoothly, with no income or home issues. I was already counting the commission from the deal.
Well, about a week before the closing, I called the couple to confirm a few last minute things, and neither one of them would return my calls. This was not a good sign. Finally, a few days later, the wife called me and was extremely apologetic. She told me that her husband had decided to leave her for a “young girl” that had been hired at his company, and that they were no longer buying the house together. I didn’t even know what to say. She sounded more angry than upset and was venting to me about how absolutely disgusting he was.
Needless to say, the deal did not close. They backed out of the deal and lost like $10k in earnest money. I never heard from the husband, so I’m assuming the wife told him she would handle it. I always wonder what happened to them. Maybe I will look them up on social media.
Anonymous Location withheld
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This is by far the most embarrassing thing that ever happened to me during a sales pitch. I was selling marketing agency services, basically managing paid ad spend on FB/Google etc. for ecomm brands. I had a lead that was a DTC beverage startup — it was some health drink that had a bunch of benefits listed on the site. I had a few good calls with them and they asked if I could have my team put together a creative pitch with concepts/ideas for their brand. This is pretty typical for the industry, and usually if the client likes the creative pitch presentation then I end up closing them.
We went into their office for the pitch. I brought my team with me. They had a big conference room with a bunch of the bottles of their drinks on a refreshment table with some snacks. The pitch went really well, my team crushed it, the client loved it. After the pitch, we all hung around the conference room for a bit, talking a bit more informally about next steps. I grabbed one of the drinks, it was some kind of green juice spinach flavored thing. I took a sip and immediately spit it out all over myself and the floor. It was warm and absolutely disgusting. I could feel my face turning beet red. I tried to gather myself but was still coughing a bit. The entire room was looking at me. In between coughs I managed to say "it went down the wrong pipe." I didn't want them to think I'd never tried their drinks before or that it was gross. The moment passed and everyone went back to chatting, but I was super embarrassed.
We still ended up closing the deal, but I learned my lesson. Whoever I'm pitching, I always make sure to actually test out their product first. I ended up trying their drinks again, and they're actually not that bad when they're refrigerated.
Anonymous Location withheld
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This isn't necessarily a sales fail but it was one of the funniest things that happened to me at work. This was before the pandemic, I was selling for a funded startup that was not doing well by any means, and everyone knew it. We were in the office every day so tensions were high. The CEO was kind of an idiot, he was good at raising money but really had no idea how to run a company. But he completely acted the part of an arrogant CEO who thought he was a boy-genius.
One morning everyone got a calendar invite for a team-wide meeting at the end of the day from the CEO. He kicked off the meeting with some motivational BS before telling us he wanted us to all come together and try to figure out "what we were doing wrong" so we could "fix the issues".
He started digging into the sales team about not hitting quota, some people on my team voiced concerns about the product team not iterating quickly enough on functionality that was highly requested from prospects and complaining that the lead quality from marketing wasn't good enough. The product team started complaining they didn't have enough devs to build fast enough. The marketing team started complaining that the CEO was micromanaging them and wouldn't give them freedom or budget to try any new ideas. The CEO was just deflecting every complaint thrown at him right back at us, he completely refused to take any responsibility.
The room started getting louder and people were angrily shouting. The CEO was visibly shaken up and didn't really know what to do. He asked everyone to calm down and said he was going to leave the room for 20 minutes so we could all take a breather. He left and we all just sat there quietly for a moment. One guy got up and said "Screw this, I'm going to Lou's, who's coming?" A bunch of us left with him to the bar we usually went to down the street. We were all drinking a few beers and one of the more senior guys was telling us how the company was running out of money and the CEO was struggling to raise more money and we'd all probably be out of a job in 6 months. People were pissed.
Anyway, I went in the next day and 1/3 of the company wasn't there. Most of the people in the bar the night before didn't show - they just straight up quit. The CEO didn't come in for the rest of the week, his admin said he was out in meetings with investors, but I think he was afraid to come in. I ended up quitting the next week, the company of course eventually went under.
Anonymous Location withheld
