Scary Sales Tales: JumpCrew Edition

The scary story blog idea came about after Jarron Vosburg told his tragic tale on a weekly team video call. When the team finished laughing on his behalf, others began chiming in with their own embarrassing sales blunders. 

Some, like Jarron’s, were more threatening than others. Nevertheless, all of the entries we received provided thorough entertainment and reminded us to double-check the details (like time zones). 

First up, the man who almost lost his fingernails.

The Tragedy Of Time Zones

In my first year as an inside salesperson, I made a common, but significant error that resulted in a pretty colorful interaction with a prospect.  I’m an early riser and a big fan of rolling calls first thing when I get to the office to help me get sharp for the day.  On one such occasion, I rolled a call to one of my leads that resulted in my leaving a voicemail around 8:30 am CST.

About 30-minutes later, I see my phone ringing, the incoming number indicating that it’s the prospect I called earlier that morning.  “Amazing!”, I thought.  Clearly, my compelling, clear, and value-rich voicemail did the work for me and they can’t wait for me to send a contract.

Wrong. I answer the phone in my most friendly salesperson tone.  “Thank you for calling JumpCrew, this is Jarron.”  There’s a moment of silence, followed by a dry delivery of the phrase, “You woke the baby.”.

I quickly realized this call wasn’t about to go the way I hoped.”I’m sorry sir?” I responded.  “You called my house at 6:30 in the morning and woke my sleeping baby.”  Cue perfectly timed baby cry in the background.  It was at that moment that I realized I had never cross-checked the time zone difference between me and the prospect.

What he said next has echoed in my mind for the years since.”If you call my house again, I’m going to come to your office, find you, and pull of each of your fingernails one by one.”

While I highly doubted the likelihood of his booking a flight cross-country for the sole purpose of violently harming my hands, I paused for a moment, quickly apologized, then just as quickly hung up the phone. His baby is probably 3 years old by now.  I’d like to think that its first word was “Torture”.

The obvious takeaway here is to never forget the fundamentals of sales, and always, check the d*** time difference.

Wicked Wifi

I’m going after some big enterprise players now and working hard to impress them with my personalization and persistence. One day a prospect at my dream Enterprise target not only opened my email 60 times because he liked my email so much, but he also agreed to set up a call with me!? I spent a couple of days typing up potential strategies, a long list of my objectives, and questions specific to his business. “I am an awesome salesperson,” I thought. On our scheduled call time, the prospect admitted a repairman showed up unexpectedly (WFH woes). We laughed and rescheduled for that same afternoon. When it came time to hop again that afternoon, I logged on to the video call 5 minutes before. I noticed my notes and the video platform were stuck loading… Then, still loading….until suddenly it was time for the call and I realized my internet was not working. I tried calling with VoIP instead. Same problem! I wrote the prospect to admit my misfortune just as he was writing to see where I was. Finally, I looked up his number and called him from my personal cell. We laughed about our mutual tech troubles, though inside I was so flustered for having only 20 minutes for discovery, WITHOUT my perfect novel of notes in front of me (not to mention no recording). I went from feeling like the best, most prepared salesperson to a total novice. We got through the call but not as I had played out in my mind. Lesson? Have a shortlist of my main goals, points, and questions on paper to ensure you keep your cool even if technology fails. Also, restart your computer once a week (not once a meltdown)!


In my first job out of college, I worked for a cool company in Chicago (Meeting Tomorrow) and was selling event technology to businesses nationwide. We had an incredible inbound lead engine and my phone was ringing all day long—it was a sales person’s dream! Since I spent all day long talking to customers, I found that I started easily losing my voice. I didn’t think that the side effect was a big deal, until one dreadful day… It was late fall, probably around 4 pm, and the day had been full of lively conversation. I was rounding out the last stretch of customer calls and was in the midst of qualifying a lovely prospect when all of a sudden, I had a scratch in my throat. The scratch quickly turned into a cough and as I went to reach for my water bottle I realized it was empty. The scratch turned into a full coughing attack and while I kept trying to mute myself, I couldn’t even squeeze out a word. Every time I tried to speak, it sounded like I was hysterically crying. I was getting nowhere with this conversation, and it was awkward for us all. I couldn’t catch my breath and the panic of this happening on a customer call was only making it worse, so I had to blind transfer the customer to one of my colleagues. My colleague was confused, my customer was concerned, and I was mortified. Needless to say, we didn’t get the deal. I will absolutely never be on a call with a customer without a full(ish) water bottle again.

RIP: “Y’all”

This is a little more funny than scary, but it stuck with me forever. My first job involved me selling paint products to body shops in the New York City market door-to-door. As expected, I was very nervous walking into the first shop on my first day. Being from the south, I wanted to make a good impression but I didn’t think to tailor my approach to this market. I walked in and yelled, “Hey y’all!” Everyone in the shop looked at me funny and then laughed to my face. “Get the F*** out of here ya redneck” said one of the guys. I couldn’t go to another prospect for the rest of the day. I just visited customers to up-sell. Lesson: it’s important to be yourself, but make tweaks to your approach based on the prospect you’re speaking to.

A Name Nightmare

A few years ago we were rolling out a new product and didn’t quite have the presentation and positioning nailed down. I was thrilled when one of the reps qualified an opportunity and booked a meeting, so I agreed (and was excited) to be on the pitch. The first call was lumpy. We were sort of nervous and were trying to find a groove, the deck was half baked, the prospect was challenging, but everything was going well enough. Until the end of the call when I opened my big mouth and called the prospect by the wrong name. He was (somewhat) gracious, he sure didn’t skip a beat correcting me, but I was embarrassed and concerned that maybe I’d blown the chance for the rep. In the end, the prospect agrees to a next steps call, so all is well. The second call, I’m on and things are the same. The prospect is a challenge and we’re still feeling things out as we go along. What did I do? I referred to him by the wrong name. Again. He calls me out. Again. Less graciously this time. I’m learning my lesson and decide to butt out. The rep does a great job getting things back on track. I shut my mouth. End of the call. Rep is thanking the prospect for his time, we have some takeaways and some homework to do, it was a really good first effort. We’re closing out the call, saying goodbyes, and what did I do? I called the prospect by the wrong name…again. We did not earn the business.

A Real-Life Goblin

I was working on a military account and cold calling businesses in Missouri for a local army base. I had called this particular bicycle shop twice before. The first time got voicemail, the second time was told the name of the manager and supposedly forwarded to his personal extension, but the call dropped. I assumed the person answering just didn’t know how to use a new phone system, so I let it go and moved on to my next call. A few days later I called again, spoke to the same person, and was forwarded to the same extension with the same result of a dropped call. This time I called right back. Upon answering, I introduced myself and asked for the manager by name, but instead of being greeted with a call transfer, I was greeted with shouted obscenities and several four-letter words and name-calling: “Can’t you see I’m (cuss word) working! You keep (cuss word) calling and disturbing me you (cuss word.)” I was shocked as you can imagine but tried to regain my composure as I was called some words I had never been called before. I explained as calmly and professionally as I could that if he had told me this on the first call days ago we wouldn’t be having this conversation, but here we are. I told him to have a nice day and hung up. I went on to check the company’s reviews and it turns out he treats his customers in a similar fashion. I learned not to take things personally and that businesses that act in that manner to complete strangers on the phone probably have some pretty upset customers.

Just Plain Horrifying

One time I was selling at an event for my previous company. The night ran long but that’s how trade show happen. I had pitched and sold a person, they walked away excited to try the product. Because of the bad reception in the convention center, I allowed the client to use my app on my phone to sign up (I had done this many times before) but what I didn’t know is he had added his contact information and ADDED ME ON “FIND MY FRIENDS” (the app) to have my location. At the end of the show, I saw him packaging up other things he had purchased and was walking to the exit at the same time as me. Again, not abnormal for trade shows. He smiled and asked how my day was, I said I made lots of sales and I was happy. We made our separate ways and I walked alone in the dark to the vendor parking lot. Fortunately, his bags were loud and I could tell he was following me. I asked if he parked nearby, he confirmed and got into his car. Two days later I was working at a separate event on the other side of Seattle and he came up to me asking if I remember him. Flabbergasted I said yes but was also getting increasingly nervous. He walked away and I didn’t see him for the rest of my shift. I got into my car and noticed a familiar car behind me. It left at the same time I did and followed me 35 minutes home. I called the police they arrived, searched my phone, and told me that he had been following my location for almost 3 days. They handled the situation and due to covid, we moved from Seattle. It was one of the scariest moments of my life. What I learned was not to let people touch my phone and don’t talk to strangers… Oh and P.S. he was not a scary looking gentleman, he was quite polished and well-spoken.

A Chilling “Hello?”

I had a point of contact who had passed away on my in-between calls. I spoke with them the day prior and followed up the next morning when their daughter answered the phone. In the midst of the confusion from both of us, she informed me that they passed in the night. I cannot emphasize enough how speechless I was. What I did learn was how to be VERY fast on your feet in pivoting from business to compassion extremely quickly. 10/10, would not recommend.

Scary Starbucks

I worked at Starbucks for just shy of a decade, and during that time I’ve experienced several technical difficulties with the POS system and upset customers withdrawing from their daily coffee intake. But one day, there was an unexplained error between Bank of America and Starbucks transactions. Sale after sale people’s cards would decline the purchase. Take about a nightmare. Starbucks was a firm believer in surprising and delighting customers, and the store manager allowed us to purchase the beverages of the customers whose card was declined. This was a very kind gesture but it causes an annoyance with the non-Bank of America customers that day. I had a lady throw her cup of freshly brewed coffee at my head because her drink wouldn’t be free. I ducked and thankfully she missed. Cleaning up coffee off of a wall was much less painful than a first-degree burn to the face. I understand that the store manager was trying to create repeat customers and I would have made a similar call if I were in their shoes. But what I learned that day, and several times since, is doing what is seemingly the right thing, isn’t always easy or a popular decision. Out of the few customers that were frustrated with the beverage not being comped, most were grateful that they could still go about their morning routine fueled by a delicious cup of coffee.

Creepy Critters

On a regular Tuesday at the office, I received an inbound call. Typically these were a customer refilling their medical supplies for sleep apnea. 

Today, however, I was blessed with a machine fix caller. If you’re imagining a frustrated 80-year-old on the phone with an annoyed 23-year-old, walking through each button press, you nailed the scene.

It turns out that nothing was “wrong” with her machine…

She made a practice of leaving the water in her machine during the day and nearby ROACHES were apparently thirsty. Her machine was infested with ROACHES.

To make matters worse, Medicare shockingly doesn’t cover roach infestations. So I had to deliver the news that the patient would have to pay out of pocket for a new machine which wasn’t cheap. 

The name-calling that followed wasn’t unusual as I spoke with 250 of these patients DAILY (inbound and outbound).  

Pretty much everything about that job was dreadful, but this specific call, I’ll never forget.

Thank you for reading our scary sales tales. Good luck on your next call.