Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, . (Don't worry, you'll remain completely anonymous).
I sell swimming pools in the suburbs. Last month, I had what seemed like a sure thing — a couple who'd been planning their backyard pool for over a year. After weeks of back and forth, we were meeting to sign the contract. Their house sat on a long private driveway, probably 200 feet from the street, so I parked in the driveway near the garage. The husband and I were in the backyard going over final details and discussing the timeline when his wife came rushing out, absolutely livid. Apparently, she had backed out of the garage without looking, not expecting a car to be there, and hit my car with her SUV.
But instead of apologizing, she was furious at me for parking there. I stood there stunned, trying to process how her backing into my car was my fault. I apologized anyway, explaining I didn't realize parking in the driveway was an issue, desperately trying to salvage the deal. But when I walked around front and saw damage, I was pretty pissed. I was already not having a great week. I exchanged insurance information in complete silence with the husband—the tension was thick. I left without a signature, and they went with another pool company the following week. My car repair is going to cost me almost as much as the commission I would have made.
Anonymous Location withheld
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I’d just started as an SDR at a Series C startup that sells competitive intelligence software. Basically a tool that helps investors and execs track what their rivals are doing. I was a few days into ramping and eager to prove myself, so I started building my own list of “high-value targets” to cold call.
After a couple hours of hunting on LinkedIn, I pulled together a list of VCs who seemed like ideal customers. About 10 dials in, I finally got someone to answer. I had just introduced myself and the company when he cut me off: “Wait, who are you with?” I repeated the company name. He paused and said, “You mean the company I invested in two years ago?” I think I let out an audible “uhhh." Before I could mutter an apology, he said: “Bold strategy, cold calling your own board. Good to know the sales team is out here hunting.” Then he hung up.
Apparently, he told our VP of Sales (who he was good friends with) about the call. I didn’t get in trouble, but it was definitely not the first impression I wanted to make on my boss’s boss. The story spread fast. The next day when I got to the office, someone printed out a list of the names with all our investors and phone numbers and taped it to my monitor with a note that said HOT LEADS FOR YOU.
Anonymous Location withheld
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I sell project management software and had been working on closing a deal with a consulting firm for months. This was potentially my biggest commission of the year. I was working from my tiny NYC apartment where my desk was crammed into my bedroom. I'd been traveling all week for client meetings and my room was an absolute disaster. I always used a virtual background during sales calls because I didn't want prospects to see my bed in the background, so I spent my time preparing for the call rather than cleaning my room, I didn't think it would be an issue.
The call was going well. We'd covered all the technical specs and he seemed ready to move forward when I noticed his expression suddenly change. That's when I realized my virtual background had cut out and he was now staring directly at my unmade bed and greasy takeout containers on my nightstand. His face went from interested to visibly appalled as he took in my chaotic living situation.
I tried to make a joke, telling him the house cleaner wasn't coming until tomorrow, but he just seemed more uneasy. I was embarrassed, so I wrapped up the call and followed up over email with next steps. He didn't respond for 3 days, so I emailed him again. He let me know they'd be going with a competitor instead. It had to be because of the unfortunate background reveal. Thankfully, I now have a 2 bedroom apartment and dedicated office, with a background I'm actually proud to be seen in front of on sales calls.
Anonymous New York City
