Funny Sales Stories for National Salesperson Day


It’s National Salesperson Day, and to celebrate, these sales experts have shared a funny and memorable story about landing a deal.

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George Gallegos, CEO, Jitterbit

“On an important call late in the sales cycle, negotiations were getting intense. Neither side wanted to back down from the numbers that had been shared. But at a crucial point in the conversation, the party we were selling to forgot to hit the mute button on their conference line. We overheard them raving on and on about how much they liked the product, and we knew they were completely sold. Knowing this gave us the leverage we needed to close the deal on our terms. The moral of the story? Always check that mute button; it could save you some money.”

George Gallegos (via The Arcata Eye)

Steve Ackley, vice president of sales, Altiscale

“In the late 90s, I was working for Tivoli Systems, which had just been acquired by IBM, and was working on a deal with Charles Schwab. At this time, enterprise software sales representatives always wore suits and ties, even on Fridays. We were actually 
much more formal than other parts of the country. However, while my first Charles Schwab meeting cemented our relationship for the deal, it also challenged my wardrobe choices. To my surprise, when I entered the meeting at Charles Schwab, they claimed it was a ‘no tie zone’ and proceeded to cut off my tie and pin it to the wall. Ultimately, we closed the deal (my biggest yet), which resulted in the ongoing joke that I could now afford to buy a new tie.”

Jane Riley, director of sales and operations, eH+ by eHarmony

Funny Sales Stories for National Salesperson Day (via devil’s advocate – blogger)

“I have always considered myself a tough and well-seasoned negotiator. Having spent most of my career in sales, I have negotiated everything from multimillion dollar real estate transactions to terms of service for eH+ premium matchmaking. I have gone head-to-head with some of the best CEOs and COOs in the business, but my most formidable opponent is still my 4-year-old daughter Jillian. Her ability to be both charming and contriving while also vehemently refusing to eat her vegetables is a skill unlike any other. Her negotiation prowess is unmatched, especially at nap time. Negotiating with Jillian and her little sister Lilly has taught me to be patient, empathetic, and open-minded, and has made me a stronger negotiator and more appreciative parent.” 

Andrew Peterson, CEO, Signal Sciences

“In college, I worked in retail sales at The North Face, and my favorite customer interactions were always the ones when I’d recommend the customer go somewhere else. Don’t get me wrong, I loved The North Face and all of their products! But I was always more intent on getting the customer the best product for what they were looking for. When that wasn’t something from our company, I’d tell them what they should get instead and where to get it from. Funny thing was, they always ended up buying at least something from me because they were so shocked I wasn’t just pushing our products on them. A great lesson I learned from this is that the best salespeople are the ones you trust.” 

Andrew Peterson, Signal Sciences – between (via Medium)

Julia Jacobson, CEO and co-founder, NMRKT

“I have this problem – it’s like dyslexia for common sayings. Even phrases I’ve heard a thousand times come out of my mouth scrambled. During our biggest sales pitch to date, my co-founder and I walk into the corporate offices of our dream customer with every detail of the pitch squared away. Everything is going great. We nailed it. A couple hours later my co-founder Slacks me…’There was something you said in the meeting…’ In my excitement, I had blurted out, ‘You will be playing yourself at a disadvantage with our product’ instead of saying either ‘playing to your advantage’ or ‘setting yourself up for a win.’ While we got the contract, I will always be embarrassed about that meeting.” 

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