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RevOps Scares to Share: 2023 Winners

Sir Ding
October 31, 2023
RevOps Scares to Share: 2023 Winners

In the world of revenue, every department has its tales of horror, but in Revenue Operations, these tales can be uniquely chilling... 

From the missteps of mismanaged data to the eerie silences of lost prospects, the haunting stories from the trenches of RevOps were enough to make even the bravest among us shiver out of our bright-orange Rattle-brand socks. I still, personally, won't be able to stay at home alone in the dark for the next couple weeks.

As promised, we’ve chosen five of the most spine-tingling, hair-raising, and downright ghoulish stories from professionals just like you (out of 94 submissions — thank you for sending them in!) So, light a candle, grab your favorite Halloween treat (Kit Kats, ahem) and prepare to embark on a journey into the darkest corners of RevOps with these tales of sheer terror!

Happy reading — and Happy Halloween!

The Tale of the “OoOoO What Does THIS Button Do?” 🔘👈

Basically, there was a button in the system which, when you pressed it, sent out an email to the customer reminding them of their overdue invoice. Simple, 1 to 1 comms, but the email’s vibe was like ASSERTIVE. We’re talking “If you don’t pay we’ll kick you out of your business-critical systems”.

So it was the nuclear option for really, really bad payers and the step before it goes into debt recovery. 

System admin went ahead one day and moved us from classic to Lightning Salesforce, straight to prod no testing. For some reason, that caused the functionality of that button to change. [Editor's note: Dun dun dun!!!]

Now, instead of sending an email to just one customer, clicking the button would send out an email to EVERY SINGLE CUSTOMER telling them that their invoice is overdue.

Anyway, someone pressed the stupid button within hours of the update because “They wanted to see what it would do.”

They weren’t even trying to achieve anything, just clicking about. Bless them it was the most stressful work day of their life. Absolute chaos ensued. We actually had someone threatening to churn for real because they felt we treated them with contempt. 

Guess who had to go to a 2-hour GDPR incident meeting because of it? And 6 hours of “how do we make sure this doesn’t happen again” meetings? And actually sort out the mess? Ops. Why would it be a sys admin? They did nothing wrong!

The moral of the story is: Don’t have a random sideline team managing your Salesforce instance. And test your bloody releases!


The Tale of the Unbelievably Good Deal 🙈

In my role as a RevOps analyst, I diligently segmented our diverse customer base to optimize marketing strategies.

One day, I received a request from our marketing director to create a specific segment for an upcoming offer. With careful consideration, I set the criteria: healthcare industry, more than 100 employees, North American location, and no purchases in the last six months.The moment of truth came when I attached the segment list to an email and hit "send."

Hours later, the response was ecstatic.

The campaign was generating impressive results, raking in over $1 million in revenue. 

However, [Editor's note: Dun dun dun!!!] my joy turned to dread when I reviewed the email and realized my catastrophic oversight.

The first line of the email began with "Dear Doctor," and it hit me like a bolt of lightning... I had forgotten a crucial criterion – that the customers had to be actual doctors. I had unwittingly offered a doctor-exclusive discount to thousands of non-doctor healthcare professionals, creating a RevOps horror story.

The Tale of the Malevolent Software 🤖

In the depths of my RevOps career, I encountered a nightmare that still haunts me to this day. It all started with a seemingly innocuous system update.

We were rolling out a new version of our subscription management software to improve billing accuracy. 

However, [Editor's note: Dun dun dun!!!] as the update progressed, a critical bug emerged, causing our billing engine to go berserk. Invoices were sent to customers at random intervals, some even receiving monthly bills for thousands of dollars when they shouldn't have been billed at all.As we scrambled to stop the impending chaos, our support team was inundated with frantic customer calls and emails. 

The horror of having to explain to our valued clients that their bank accounts would be overdrawn due to our software's malevolence was heart-wrenching.

It took days of round-the-clock work to fix the issue, refund the overcharged customers, and regain their trust. 

The lesson was clear: even the most well-intentioned software updates can turn into RevOps nightmares if not thoroughly tested and monitored. It's a Halloween story I'll never forget, and it serves as a chilling reminder of the importance of quality control in Revenue Operations.

The Tale of the SSO Nightmare 🔒

I was employed at a sports gambling company, and the pinnacle of our year revolved around the commencement of the football season. I held a position within the revenue department, and our team was experiencing remarkable success due to our collective efforts. However, our fortunes took a sudden downturn when an email arrived from the CEO. The email contained distressing news [Editor's note: Dun dun dun!!!] - the team had not only botched the Single Sign-On login migration, but they had done so at the most inopportune moment: the very start of football season.

As a startup, this one week carried immense significance for the revenue team, as our performance during this period would determine our success for the entire year. With approximately one million members unable to access our service during this critical period, the situation became dire. To compound matters, we had only one customer service agent who was already overwhelmed with work. In my experience, this was arguably the most nightmarish scenario in the realm of revenue operations that I had ever encountered.

And we never did learn what happened to all those lost souls….

The Tale of the Extra Keystroke 🧮

One extra key stroke almost cost us 1/4 of a million dollars. One minor mistype, was the most costly mistake I’ve made to date in my career. 

Instead of typing 3, I accidentally also hit the 2 in front of it, loading 23 allotments. [Editor's note: Dun dun dun!!!]

That’s 20 extra spots that came with a cost per tour. 

That’s 20 extra tours, we didn’t have Sales reps scheduled to sell to. 

That’s 20 opportunities that we couldn’t even pitch. 

That’s $250K straight down the flusher because of that one little keystroke. 

I checked this schedule nearly daily, weekly, and monthly to prevent mistakes like these from occurring. I spent hours every day just on this one project and couldn’t dedicate myself to supporting my team as much as I wanted. So how could this happen?

Here’s what I learned: Manual processes can leave for a greater loss as much as it can be an expense saver. Read that again. Don’t forget to calculate the manual labor hours and potential margin of error when debating when you should automate a process or implement a tech tool to solution that gap. 

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