The War Room

Hilarious or Crazy Sales Stories - Let's hear 'em!

I'll start. With COVID we shut down all on site demos and onsite sales meetings. I had this one particular prospect who was always on my "what a dick" list. So every year I reached out to him more as a joke and to be an asshole since I knew he was overpaying and my solution would be a much better fit for him, but he was using "the Cadillac" in our industry and liked to remind me of that each year. Flash forward and now a worldwide pandemic is going on and I email him a "Hows that overpriced piece of shit working for you? Maybe this is the year?" type of email and he actually responses saying he wanted to learn more! BUT - he would only entertain the thought of switching if I came onsite and met with them...... in a pandemic. Typically the answer is to start at least with an online meeting but this particular prospect is located just outside of Las Vegas - so I happily agreed! Haha. (P.S. totally nailed it and got the deal and had a great night at the same time!)

๐Ÿ˜‚ Sales Humor
Valued Contributor
Business Development Manager
One of my first big boy sales calls. I was wearing my only suit. I got there early trying to be a good salesperson so I had some time to kill in my car.

Had to get a fart out. Leaned over in the seat and let out a quick BRAAPP and immediately knew I fucked up.

A squirter came out. Had to divert to a McDonald's to trash my boxers, rinse out my pants and dry them as best as I could with people beating on the door. Ended up like 12 minutes late to the appointment. Didn't get the project. Just all shitty.

Well that's a "shitty" situation. Bet that client would have been "crappy" anyway. Sounds like that was a real sticky situation. But either way that "stinks" man. There's no recovering from that haha.ย ย 
Here's another for you:

Was working for a company selling into police departments 15 years ago and the CEO instructed me to get us sales on the East Coast. Lined up a few leads in the Boston area and scheduled to fly out there for some meetings and also kick in some doors. The CEO said he would tag along to "make sure these leads get closed". We went into the very first department on a straight cold call and the gatekeeper told us to "Get the fuck out of my department and don't ever fucking come back. We don't need your shit and we hate salespeople". That was the first AND LAST time my CEO ever tried his hands at sales. He didn't go into another department the rest of that trip.
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