Halloween Horror Stories Series

Halloween Horror Stories Series

Horror Stories from Real Sales Reps banner

Real Blood-Chilling or Embarrassing Stories Told By Reps Like You

We collected real stories because they are better than fiction!


Halloween Stories Contest

You had a terrifying, embarrassing, near-firing situation that still pains you when you think about it?

Make the world hear it!

You can win $50 and let everyone know what you lived through and survived to tell it.

Don’t worry, you don’t have to be embarrassed again.

We can publish it anonymously, if you prefer.

Or, get some publicity – there is no such thing as bad publicity!

Send your story to [email protected]

The contest runs till November 30, 2019. Winners will be announced no later than December 10.


Launch Interrupted

MT., Major Accounts Executive, 30+ Years in High-Tech

I worked for the up and coming startup, a supplier to the giant industry of very few players, many years ago. The company spent almost five years building up a new division that’s in a very established space offering a complete product distribution platform and ongoing operations services. We were going after very large deals comprised of the equipment for the central office, for the field, services and supplies for delivery and installation. And the operational services, of course.

Our customers were Tier 2 regional buyers, many of whom I knew personally and built the pipeline using my connections. All our sales materials, the pitch, and the marketing collateral were talking about how much experience we had, how reliable we were, and that we were here to stay. Our number one goal was to make people trust us.

We had field trials in progress, I was traveling to big clients all around my territory. The prospects spent a year of solution engineering and trying out with us.

And then, one day, two weeks before the biggest trade show of the year in the industry, the CEO killed the entire project. Closed the business unit.

I staked my personal reputation on this company promising people that we were here to stay. This change in direction really ruined my name and my career in that space.


Mistaken Identity

Pamela Z., Business Development, 30+ Years in High-Tech, Telecom and Security Sales

I was scheduling an extraordinarily critical business meeting for a conference call. The key participant was THE decision maker at a multi-billion dollar company, BIG COMPANY.


So, I invited Alex Dumbledorf via email from BIG COMPANY and he accepted the invite but kept asking “are you sure you want me on this call?” My response? “Of course, you’re the most important person.”


My executive staff was on the call and Alex Dumbledorf called in. 


I could have crawled under the tile in my office. Our email system (Microsoft Outlook) selected Alex Dumbledorf from within the company automatically and not the Alex Dumbledorf from BIG COMPANY. Who would ever think there were two such odd names in the world?!
I looked like an incompetent fool and we missed a huge business opportunity.


Animated Cold Calling Turning Wild

Mimi Evans, Seligence Co-Founder, 30+ Years as a High-Tech Sales & Partnerships Rep

Mimi, you have been cold calling for over 30 years, any scary moments that come to mind?

My partner and I had to generate leads on behalf of the client, a small British company that launched on the U.S. market to compete with the antivirus giants – Symantec, Norton, McAfee. They gave us the list of companies that my partner and I split in half and started calling on. Not surprisingly, nobody returned our calls because it was a no-name company in the U.S. that tried to move from mid-market to enterprise at the same time as they opened the new country.

It was a tough job. Some days, when we were desperate to talk to someone live, we would call each other just to hear a human voice on the other side of the phone to get motivated and not to lose it. With one caveat – I would make monkey calls and he would make donkey calls. We were really going crazy from days and days of calling.

So, when my phone rang one day, I didn’t think much of it and answered with the usual “yee-haaa-huh-huh,” because the only person that it could have been was my partner. When silence ensued, I felt my blood turning cold and my feet shaking in horror. “..Uhm… I was looking for Mimi Evans from Sophos,” said an unsure soft voice on the other side.

To say I was embarrassed and terrified would be an understatement. Somehow, I waltzed out of this sticky situation and the caller turned out to be our first lead. Out of many that followed. I still feel the chill down my spine though when I think about it.


My Flashy Sales Kickoff Stage Performance

Anonymous Embarrassed, Major Accounts Rep, 15+ years in High-Tech Sales, selling for the Top leading company in its space

What is the scariest story from your sales career you can remember?

I was presenting at the annual company kickoff with the audience of about 300 people in the giant ballroom of a Boston hotel. My speech was about accelerating your process and closing more deals using my company’s product. In the previous year, I hit over 150% of my sales quota and won several major accounts.

I was ready and on fire. I spoke for about 15 minutes, got some good nods and laughs from the audience, some applause and left the stage to go to use the restroom after I was done presenting.

As soon as I got to the restroom, my heart dropped, and I was shaken more than I ever was on stage. I had my gray suit on, and I noticed my fly was wide open with the burgundy red underwear clearly showing from underneath. I was never so mortified in my life.  I had to return to the event, but it was so hard to put on a poker face. My buddies who were in the audience, made a few jokes about it later on, carefully, making sure I wasn’t going to pass out. 

Since then, I have a paranoia: before every meeting, every time I need to be somewhere – I make sure I check it. And I still love to wear red burgundy underwear. I guess the lesson, with everything we do, is you have to pay attention to detail with everything!


The Panic Room

Panicked and Late, Major Accounts Executive, Sales Director, 20+ years in High-Tech and eCommerce solutions

Any really bad days from your long sales career that you wished would have never started?

The biggest and worst nightmare of my 20+ years sales career was the only sales meeting I was late to. I usually am earlier to all my meetings by 30 minutes or so to let me have enough time and set up the equipment, meet up with prospects, get a sense of the room, etc.

On that day, there was a huge traffic jam on the 93 South and I was running late to my first in-person meeting and demo with J.Jill account, the women’s clothing company. On that day, I was the only one from my sales team coming there in person – the rest of the team was dialing in remotely.

The meeting has already started as I was still stuck in traffic. Walking in 10 minutes after the meeting kicked off, I was already in panic, and as soon as I opened that conference room door, I started having a real panic. I was walking into the room with 10 people sitting around the table just looking at me. The buyer brought everyone to attend our very first meeting: Marketing, eCommerce, Analytics, IT.

The nightmare didn’t stop there – in that conference room they had really old technology: I couldn’t properly connect my Mac laptop to the projector. They called an IT guy who couldn’t figure it out either.

The IT guy offered me to use a loaner PC, which wouldn’t work because I had all plug-ins, all setups properly configured for our solution and for the demo on my Mac. I just had to wing it this time, only had a few minutes of the demo really with just my laptop in a room of 10 people.

After the meeting, my main point of contact said that it was terrible, he gets that it wasn’t entirely my fault, but still: it was a tough audience and a tough account. A week later, myself, my manager and only four key people on the client side met at a different conference room to go over our demo. Second time was the charm – we did well enough to win the deal. 


The Legally Crazy Case

Dan Freeman, 30 Years in Sales, Chief Revenue Officer, InSegment, Digital Marketing Agency Ranked #6 in Boston & Chief Sales Revenue Officer at & INFUSEmedia, a B2B Lead Gen Agency, #54 in Inc.5000

What was the day of your long sales career that you wish had never started?

It was many years ago when I was involved with the company selling business voice and data services. We had a law office in New York City as a prospect and promised to them to install the service remotely with no interruption to the business. He gave us the deal and somehow the technician from the company came to his office and cut the line. Don’t remember the details of how it happened, but basically the client had no phone in his office for several days.

It was when he called me and left the voicemail that I will remember for the rest of my life. It started really nicely with “hi, this is so and so. I am your customer from XYZ law office, you promised me to get the service installed remotely and that was fine until your technician actually showed up and cut off my line.”

As he was speaking, the tone of the voice was starting to get harsher and harsher until the moment when he was yelling and cursing into the phone.

“Do you know how much it costs me in business lost not to have that phone working? And I know who you are and where you are, and I will come after you and hunt your ass down and kill you.”

I was so terrified to hear this voicemail. I played it out loud for the whole office and they also were mortified.

We quickly dispatched some remediation resources and his service was back up. Haven’t heard from him since. But in that moment, that was scary. After that, for a while, when visiting New York City, I had to keep my eyes in the back of my head, just in case. Really don’t worry much about it these days…


Capture the Error Code Race

Tech Chick, 25+ Years as a Major Accounts Sales Rep in Technology, Selling Cloud and Managed On-premise Services

Any stories from your long sales career that made your heart drop?

A major distributor in the US was looking for a new managed services partner. They opened up the official RFP process for a solution that would proactively monitor Cisco environment. It was a very complex RFP – not only did they want to monitor the network level, but they also wanted to perform monitoring higher, at the application level, including sophisticated applications like IVR and speech recognition. 

The essence of the managed services solution they were looking for was to keep a pulse on the environment, if there would be an outage of any sort, the applications would trigger an error message, alerts are pushed out, and the problem can be remediated before any service disruption.

We made to the top 3 vendors after 4 months of the sales cycle. It was a major 3-year contract with the major buyer, so we were excited to keep going.

This is when the buyer sent us the email with the error code that was not captured by their current provider and could not be remediated, if it occurred. The email said that if our solution was able to duplicate this specific error code and show that we can catch the error, identify and remediate it – we would win the deal. 

This is where I said: “Are you kidding me? One specific error code is really hard to get. There are thousands of them. Plus, everyone’s environment is very unique – how can we duplicate his environment?” This being a huge 3-year contract, I called my technical team to see if the test environment we had was able to produce this error code. They looked at the request and said: “Are you kidding? There are thousands of codes – how can we duplicated this particular one?” Our tech team had a simulation lab and so they promised they would try but it would be very difficult to duplicate it.

Then, in a few days, I meet the client at Westin in Waltham, and we are sitting down to talk about the next steps. Carefully, I brought it to him. “I have to speak to you about this. This is a unique error code. If we cannot duplicate it now in our lab, can you give us a chance to duplicate it in your unique environment within 30 days? Can you give us an opportunity to try?” 

He didn’t give a response, made the “will think about it” nod. I leave the meeting with uncertainty on the deal but had proposed the best alternative, if we could not duplicate the specific error code in our lab. Within a few hours I got a call from my team in the lab. They worked on duplicating the code and had success!   I literally was screaming: “How did you duplicate the code?” “We pulled the plug out of the wall on the server and it triggered the error code.” (are you kidding me?) We had to show that our monitoring tool will capture the error code, trigger it for remediation whether it be automated or with human intervention. The results were shared with the prospect and we won the deal!


Sky-High Pile of Junk Leads with Even Higher Goals

Justin Miller, Manager, Demand Generation Team, edX

What was the biggest horror story in your marketing career?

One time I was hired to take over a marketing team, and inherited aggressive lead goals. The goals were based on the fact that the company was getting a very high number of inbound leads. When I dug in, I realized the lead targets were unusually high because the qualification for a “lead” was someone coming to the site to download a gated resource. It was a very light “gate”: a single-field form that just asked for email address, with no email verification step to validate it.

This meant there were literally tens of thousands of bad leads in the system that gave us no ability to segment or personalize content, and, ultimately, hurt our email sender score every time an email went out. 

Sounds like a bad cycle to be caught it. How did you solve this nightmare?

We changed the form to ask for person’s name, email, and another question that allowed us to categorize the type of persona they were. We also went through the existing email list and pulled out any email addresses with terms like “test” and “email” in them, to clean it up from junk.

Once we did that, we looked at the volume of addresses that hadn’t opened an email within 12 months and removed those people as well.

Once the dust settled, we were able to reduce our email marketing lists size by over 35%. This didn’t solve all our problems, but it at least gave us a better shot at building campaigns that provided actionable data for us to use and iterate off going forward.