40+ Humorous Sales Jokes for When You’re Being Upsold

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Let’s face it, salespeople often get a bad rap. They’re seen as smooth talkers who promise the moon but deliver little more than fool’s gold. Alec Baldwin’s famous line from Glengarry Glen Ross, “Always be closing,” perfectly encapsulates the stereotype. But let’s look at the brighter side: salespeople hustle hard, wield impressive charm, and possess confidence and resilience that’s admirable. Plus, some of the most beloved characters in pop culture are salespeople, from Michael Scott and Dwight Schrute in The Office to the ever-pleasant Jim Halpert.

To celebrate the lighter side of sales, we’ve compiled a list of hilarious sales jokes that even your local used car dealer would find amusing.

Sales Jokes and Puns

1. Why did the footwear salesman dance all day? He had a lot of sole!
2. How can you tell when a salesperson is being dishonest? Their lips are moving.
3. Why was the salesperson let go from their amplifier job? They couldn’t generate enough volume in sales.
4. Why did the Velcro salesman resign? They couldn’t stick with it.
5. What’s a fitting name for an insurance salesman? Justin Case.
6. How did Yoda secure his first lead? He utilized the SalesForce.
7. Salesperson: “This computer will halve your workload.” Office manager: “Fantastic! I’ll take two!”
8. Which salesperson has the slickest pitch? A hair grease vendor!
9. What are the three benchmarks of a sales manager? A) Carpet thickness in their office. B) Desk size. C) Engine size of their car.
10. How do salespeople typically greet one another? “Hi. Nice to meet you. I’m better than you.”
11. What did a carpet seller give his wife for Valentine’s Day? Rugs and kisses!
12. What knowledge is essential for a real estate salesperson? A lot!
13. Salesperson: “Interested in a pocket calculator?” Customer: “No, thanks. I know how many pockets I have.”
14. What does a hat seller drink to kickstart his morning? A cappuccino!
15. The salesman claimed the shoes were made from alligator, but I knew it was a crock.
16. Always trust a glue salesman; they stick to their promises.
17. A man who sold boomerangs is attempting a comeback.
18. A sales manager addressed an underperforming team: “This month’s contest will see the winners qualify for next month’s!”
19. Salesperson at a dinner party: “Oh, you work 40 hours a week? I remember my first part-time gig too.”
20. Boss: “Did you secure any orders today?” Salesman: “Yes, I got two!” Boss: “What were they?” Salesman: “Get out!” and “Stay out!”
21. Patient: “Doctor, help me stop talking to myself.” Doctor: “Why?” Patient: “I’m a salesman, and I keep selling myself things I don’t want.”
22. A customer confronted a sales associate: “You said these pants were pure wool, but the label says ‘100% cotton.’” The salesman answered, “Oh, that’s just to keep the moths away.”
23. As a rock salesman, I’ve had great success with money. Sometimes I take it for granite.
24. Did you hear about the traveling pasta salesman? His commission was penne’s on the dollar.
25. A traveling salesman walked into a bar. The bartender asked, “Why the long face?” Salesman replied, “Amazon.”
26. Bought a Christmas tree today. The salesman asked if I was going to set it up myself. I said no; it’s going in my living room.
27. What does a cowboy car salesman say? AAAUUDIII!
28. A man’s wife left him for a tractor salesman. She wrote him a John Deere letter.
29. I shouldn’t have purchased balloons from a salesman with commitment issues. There were no strings attached.
30. What do you call a bike tire salesman? A spokesperson!
31. What’s the distinction between a used car salesman and a computer salesman? A used car salesman knows when he’s lying.
32. My first job was as a door-to-door salesman. I sold “no soliciting” signs.
33. Why did the girl fall for the ginger ale salesman? She was Schwepped off her feet.
34. Did you hear about the battery salesman? He charged too much but got positive reviews.
35. The salesperson presented a PowerPoint on the water park we’re visiting. It had several slides!
36. What’s the difference between a brick salesperson and a boxer? One stocks rocks, and the other rocks socks.
37. Why were the German salespeople thrown out of the sausage convention? One of them was the wurst person ever.
38. What did the sales leader say when the telemarketer asked if she read any magazines? “I do periodically.”
39. What did the sales rep say when his manager said, “The word ‘impossible’ isn’t in my dictionary!” He replied, “Sir, didn’t you check inside before buying it?”
40. Three violin makers in Italy had been competitors for years. The Amati shop claimed, “We make the best violins in Italy.” The Guarneri shop proclaimed, “We make the best violins in the world.” Finally, the Stradivarius family declared, “We make the best violins on the block.”
41. A salesman demonstrated unbreakable combs, bending one until it snapped. He then held both halves up and said, “And this, ladies and gentlemen, is what an unbreakable comb looks like on the inside.”

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In summary, sales can be a hilarious field filled with memorable characters and funny moments. Whether you’re facing an upselling salesperson or just need a good laugh, these jokes offer a lighthearted take on the world of sales.