Sales Fails: "I assumed OOO meant a prospect was on vacation. I was extremely wrong"

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I still almost can’t believe this actually happened to me but it really did. I sell SaaS (Account Executive) and most of our target customers are smaller startups. In some ways, this is good, because I’ve found it easier to get through to decision makers, but in some ways (as you’re about to find out) it can actually be bad. 

So last year, when everybody was raising their big funding rounds, there was a company that I was pitching. They had just raised a nice seed round, and our product was a pretty good fit for them. I got through to the cofounder, who seemed nice enough but definitely took himself pretty seriously, and things were moving along. Great, right?'

Well, at the same time I was pitching this company, I stumbled across one of their competitors. This happens a lot when you’re selling to early stage companies – you discover similar companies who might want to use your product too. It actually tends to work out quite well in a lot of cases. 

So, like I usually do, I started interacting with both of these companies (which compete with each other) on LinkedIn. I wasn’t going over the top or anything, I was just liking their posts and commenting a few words on any big announcement. No big deal, right?

Well, I got an email from the first guy I talked to (the cofounder who took himself pretty seriously) which said that they were in direct competition with the other company, and that by “promoting them” (all I did was like a few posts), I was costing them money, so therefore, they wouldn’t be able to do any business with me or my firm “ever again.” I honestly could not believe it – it had never, ever been a problem before. I think that cofounder is going to have a hard time succeeding in business if he’s that thin-skinned. But it’s still a Sales Fail!  

This is definitely my biggest Sales Fail, even though I actually did end up closing the deal, especially since I’m always extra careful when dealing with prospects. 

I sell HR software. A little over a year ago, I was working on a deal with the COO of a medium-sized company. It was a great account and I had a very professional relationship with the COO and a few people on his staff. We kept it all business, and things were going well. 

Finally, after months of demos, follow-up, and approvals, I got word that the deal was going to go through. I was pumped! All we had to work out were the logistics of getting the contracts signed with final redlines from legal.

So I emailed the COO with some questions about getting everything ironed out. He quickly responded and said that he was going to be out of the office for the next week and that he would handle it as soon as he was back. I responded, “No problem. I hope you enjoy your vacation!” 

Well, about a half hour later, I got a response from him, and it said: “Not a vacation. My mother passed away unexpectedly.” 

I wanted to crawl into a hole and die. I emailed him back and apologized profusely and gave him my condolences. It took him a few nail-biting hours to respond back, but when he did he said it was no problem and that he appreciated my kind words. Let that be a lesson to everyone: never assume anything! 

Anonymous             Location withheld

In the early 2000s, I briefly sold motorsports before moving into cars and eventually mortgages, which is what I sell now. I was pretty good at it, and I was young enough where even making 70k a year felt like making a fortune. Those were the days lol. 

One day this guy came in to look at a used Suzuki GSX-R. He was a restaurant manager or something like that, and was really friendly and nice. My manager worked the deal, and he ended up signing for the bike and coming back to pick it up the next day.

About a week later, he called and said he wanted to return the bike. My manager tried to be nice at first but basically ended up laughing at him, like there’s no way that’s going to happen. The guy kept calling for the next few days, and was getting increasingly irate. Still, my manager said no way – you bought it, it’s yours. 

The next week, when we went to open the building, our power wouldn’t come on. We called the power company and they came out and saw that someone had cut the power to our building and to the D’Angelos next door to us. We kind of suspected that it might have been this guy and we filed a police report but nothing ever came of it. 

Then, we got a letter from a lawyer, basically laying out the ways in which we supposedly “deceived” this guy into buying the bike. It was absolute nonsense, but my sales manager discussed it with the owner, and they decided to take the bike back just to avoid dealing with any more headaches. 

Well, fast forward a few months. I come into work and they’re all laughing about something. So I ask what’s so funny. My manager says, “You remember that crazy guy who returned his bike?” I said yes, and he says: “Well, that letter from the lawyer he sent us. It was completely fake. He typed it up himself.” It turns out that this guy concocted an entire fake law firm, with fake letterhead and everything, and sent it to us to scare us into taking back his bike. And guess what? It worked! 

Anonymous             Location withheld    

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