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The Eight Spookiest Moments in Sales

On a good day, sales is the greatest job in the world. On a bad day, it can be truly terrifying.

In honor of Halloween, we’ve rounded up eight of the most chilling moments in the life of a sales rep. If you’ve got any sales horror stories of your own, please email them to

1) You’re coming off a killer month, and realize you have no leads in your pipeline. None.

2) Your prospect asks, “Did you catch the game last night?” and you have no idea which game they’re talking about.

3) You’re doing a screenshare demo for an important client, and your website stalls out within the first two minutes.

4) It’s the last day of the month, and the prospect who you need to close in order to hit your quota isn’t answering their phone.

5) When you see how much tax is taken out of your bonus check.

6) A prospect brings up a political opinion that goes against everything you stand for, and won’t let it go no matter how many times you try to change the subject.

7) You’re in the middle of a discovery call and the prospect starts commenting on the lovely sound of your voice.

We’ll end with this tale of terror sent to us by Penji co-founder Johnathan Grzybowski:

“Back when we were an agency, we had a digital board for each client with a list of things our clients love. We went into extreme detail because it helped us further understand who we were working with, and also if we needed to send them a gift we knew what to buy.

“Somehow, that board was added onto a proposal.

“To make a long story short our client at the time read the board, which included this sentence: ‘NAME, loves to drink a glass of white wine after work.’ It was delivered to not only her, but to every decision maker within the company. We immediately got a phone call from them, and needless to say, we didn’t get the contract.”

Related: What’s the craziest sale you’ve ever made?


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