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 happened to me towards the end of the pandemic. I was one of the first sales hires at a small startup with a bit of funding. We were growing slowly but consistently. I closed a deal with a tech company based in India (I'm located in New York) so there was a big time difference.
After they signed the contract, I sent a calendar invite for everyone to hop on a kickoff call. They specifically requested that the call be at 2:30PM their time, which was 5AM in NYC. Our team all got up and hopped on the call 10 minutes early to prepare. It was still dark outside and everybody looked like they had just rolled out of bed.
The client joined the call 5 minutes late. I started talking through the agenda, and she stopped me and said, "Actually, I came on this call to let you know that we’re canceling." She said that they no longer had the budget for the project. This was one week after they signed the agreement!
We were a small startup, and they were a little bigger but definitely not a big company. We didn't bother getting any lawyers involved and just chalked it up to a loss. I was confused at the time, since this was the only time in my career that a prospect actually signed a contract and then a week later decided they didn't want to honor it.
I laugh about the ridiculousness of it now, but I was pissed that I woke the entire team up for a 5am call for the client to essentially nix the deal, which they could have just done by email.
Anonymous New York City
My biggest Sales Fail ever happened to me at the beginning of this year. In my defense, I was pretty desperate for a deal. I'm still at the company and my team still makes fun of me for it to this day. One day I decided to cold email the CMO of a pretty large enterprise company. To my surprise he responded and actually took a meeting with me instead of passing it off (it was a pretty damn good email which took me over an hour to compose).
We got on the call, and I was charming, and he was in the market for a product like ours. He seemed really interested. But there was one small problem: my name is Tim, but throughout the second call, he kept calling me Jim. I didn't correct him at the start of the call, because I thought he had just slipped up, but he kept calling me Jim even though my name was CLEARLY VISIBLE IN THE VIDEO SCREEN. At some point, it felt like I had let it go too far to bother correcting him, so I just let him call me Jim. I just wanted the deal.
Anyway, he had some technical questions about the product so I set up a second call with a sales engineer and one other person on his team. We got on the second call with my sales engineer, and everything was going well, but he kept calling me Jim, again! There were four people in this meeting and the guy was calling me the wrong name and no one was bothering to correct him. Meanwhile, I'm just responding to my new name.
Aside from the name thing, I thought the call went pretty well. The sales engineer immediately sent me a Slack message: "Hey Jim, great job on the call." By the end of the day, the entire sales team was calling me Jim and making memes about it.
The CMO eventually kicked the can down the road, saying it's something they would potentially be interested in revisiting next year. So, even after all that, the jury’s still out on whether or not I'll close the deal. But I better close it, because right now I'm the butt of the joke and all my colleagues are still calling me Jim! Maybe the CMO will read this and realize what he did.
Anonymous Location Withheld
This happened to me back when I saw an SDR. I did a lot of cold calling and email. I had gotten a response from a prospect, he was a middle manager. I had a discovery call with him to better understand their problems and see if we would be a good fit. It went well, the guy was nice but something seemed off about him. He kept talking about himself and all his accomplishments throughout his career during the meeting, it seemed like he had a chip on his shoulder for no reason. I let him keep talking about himself anyway.
At the end of the call, he said had to bring in his CFO who was the decision maker. I was pumped. He added his CFO to the email thread and we exchanged a few more messages and set up another meeting. I was mostly addressing the CFO in the emails, answering a few of his first questions over email. We finally had the call, it seemed to go well, the CFO was impressed, but the manager I had the first call with just sat there on the video call quiet with a pissed off look on his face.
Anyway, I followed up with more info on pricing structure and next steps. I heard back from just the middle manager directly he emailed me, without the CFO cc'd. He said not to include the CFO on future email communications, which I thought was really weird. I responded to him directly, but then the line went cold for a week after that. The manager finally emailed me back and said that they weren't going to move forward. He gave me no additional info.
To this day I still don't know what happened with the deal. But my theory is that the middle manager blew the deal up because I was addressing my emails to the CFO first and spent the second call pitching directly to the CFO. I don't know if he felt disrespected but that's my theory. I guess I'll never know.
Anonymous Location Withheld