The frightening side of customer onboarding and implementations

We asked our community members to send in their scariest onboarding stories for Halloween. You won't believe what happens in the last story!
November 12, 2021
No items found.
Pay heed to these inglorious tales
Of extremely tedious onboarding fails
The choice is yours to bear the pain
Or make life easier and get Rocketlane

Getting new customers to see the value in your product - from the initial setup to configurations, integrations, data migration, and training - is no easy task. At Rocketlane, we understand how difficult and messy the entire customer onboarding process can get. If you’ve dealt with, or are currently dealing with complex customer onboarding challenges, and feel like your struggles aren’t being adequately acknowledged, do not worry! 

For Halloween, we asked our followers and community members to share their most terrifying customer onboarding stories with us to prove that you’re not alone in your onboarding woes. Here are six of the most interesting responses we received:

Responses have been edited for readability.

Story #1: Monster Spreadsheet to Manage A Monstrous Project

Contributor - Tami Titheridge, Product Engagement and Support Lead, Kapiche

Tami used to work for a company that developed customer feedback software which allowed its customers in the retail industry to leave in-the-moment feedback using physical tablets that are installed at each store location. Going from 1-10 devices per store, she was once suddenly tasked with the responsibility of servicing a major client that had a requirement of 120 such devices to be distributed across Australia and New Zealand. The project had hiring various contractors to help with the installations, setting up training sessions, coordinating with all the stores and doing a massive roll out. Tami and her CEO eventually employed a monster spreadsheet to have a bird’s-eye view of the entire process. After a whole lot of coordinating, assigning, and executing, the project was eventually completed six months later. 

Story #2: The Nightmare of Managing Customer Expectations

Contributor - Brittany Lockwood, Customer Success and Education at Dealpath

Brittany Lockwood is currently a Customer Success Manager at Dealpath, but this story comes from one of her roles at a previous company. Her salesperson made the mistake of promising one of their clients that they’d be building an integration with one of the other software systems their client uses regularly. And that was their expectation coming into the implementation process - they had even paid for access to that integration and split the cost across the three years of their existing contract. Only the product team didn't even have this integration on the roadmap yet. And the engineering team didn't have the capacity to move it up or prioritize building it. Oops.

Brittany then had to break this piece of news to the customer. Fortunately, they were on a three-year contract, so they had some time to get things figured out. While the client waited for that implementation to be built, she made sure to focus a lot on their adoption of other features on the platform, so that the client would be seeing value beyond just a data integration they had been hoping for. For Brittany, the key was to be honest with the client about the situation, take the time out to listen, and do more discovery so they felt heard. For Brittany, the scariest part of this implementation process was managing the expectations that were set during the sales process. Hmm, does this sound familiar?

Story #3: Managing “IT” 

Contributor - Richard Benavides, Client Success Manager, Videate

Richard, an onboarding manager for Videate, once had a customer come in with some very peculiar demands. The customer basically wanted to pay for one license, and then be able to let every other person that he sold his product to, to come in with their own individual logins. The customer essentially wanted to “sublet” Richard’s software, so that he could make more money at the expense of Richard’s company. Before Richard could disagree and process a refund, the customer threatened to sue and engaged in abusive language and name dropping. He then went on to berate Richard, the salesperson involved in the deal, and even the company’s director. 
Richard’s company then decided to let go of the customer and refund his money. But this did not go down well with the customer. He started threatening the sales rep’s family and friends, eventually getting him to quit working for the company with all the abuse. They all luckily never saw the customer again. Yikes. 

Story #4: What’s the Status?

Contributor - Srikrishnan Ganesan, Co-Founder, Rocketlane

Srikrishnan tells us the onboarding story of a client he had while working at his previous company, Freshworks. Sri’s team had just won a large customer from a Europe-based digital payments company and they had a very tight deadline to go live.

The client also requested for more features to be built in but didn’t have the engineering bandwidth to do it from their end. Sri’s team then roped in a third party engineering unit to deliver the additional requirements. But there were several lapses in communication that led to a lack of clarity on where the deployments stood. As they approached the deadline to go live, the engineering team finally showed Sri and his team what they had been building. Unfortunately, things weren’t where Sri wanted it to be. If he had known earlier, the engineers could have done something different. But the lack of transparency and clarity on where the project stood led to a one-week delay in delivery. Thankfully for Srikrishnan and his team, the client was very accommodating. But the days leading up to the deadline were extremely taxing since it was their first time servicing such a large client. This is one of many stressful experiences that Srikrishnan has had while onboarding customers. He believed that there must be a better way to handle the onboarding process - where everyone’s held accountable and have a transparent picture of what's happening. That's why he eventually left Freshworks to build Rocketlane so that businesses across the world can consistently deliver five star experiences to onboard every new customer.

Story #5: We’ve Got Some News

Contributor - Anonymous (name changed to Dave, product name changed to XYZ)

Video Link - NA

Dave’s is a story of a large customer they had in Europe for a product he used to work on called XYZ. During onboarding, one of the conditions from the client was that they needed Dave’s team to move their data center to Europe (GDPR compliances). But Dave’s product did not have a data center in Europe. So Dave and his team committed to the client that they would somehow make it happen. It was a long project and they had three months to figure things out. 

Exactly a month before the actual rollout, Dave had to deliver some real bad news to the client. Product XYX was going to be replaced by a new product, ABC, due to an overhaul within their organization. And this will cost Dave’s company two extra months for delivery given that they also had to factor in the delay caused because of the data center. 

It was a nerve wracking period for Dave and his team. They had to communicate the big decision to the clients, and they weren’t sure how they're going to take it. They eventually informed the clients and apologized for the change in strategy from their end. While the client was momentarily unhappy, they loved the new and improved product. What could have been a really disastrous horror story turned out to be a rather happy one for all. 

Story #6: The Dark Side of Customer Success 

Contributor - Oliver Plane, Customer Success Executive,

Finally the story of a Mrs. X sent in by Oliver Plane is a very special one. Amongst all the responses we received, this one carries the most intrigue. We wouldn’t be doing any justice to it by revealing the details of the story here. We recommend you watch the video to know what we’re talking about.

We hope these stories resonated with you. The onboarding process is generally considered a very pivotal moment in the relationship built between a business and its customer(s).

If you’ve been struggling in any way, and are looking to optimise your resources for all your customer onboarding projects going forward, give Rocketlane a try!

More resources

  1. Implementation Stories
  2. Preflight Conversations
  3. The Launch Station - a podcast for all things customer onboarding
  4. Customer onboarding resources from Rocketlane

Industry insights you won’t delete. Delivered to your inbox weekly.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.
Rahul Sridhar
Content Marketer @ Rocketlane

Content Marketer at Rocketlane. Former teacher turned tech writer. Occasionally dabbles in comedy and rap music.

You might also like...
Here are some other posts from us you may enjoy reading
Customer onboarding benefits for retention and acquisition
Learn how to build brand loyalty and retain customers. Discover customer onboarding and how it impacts customer acquisition and retention.
Understanding float and why it matters in project management
Explore the importance of float in project management. Discover how flexibility impacts success, risk mitigation, and resource allocation.
Benefits of implementing expense tracking in a PSA tool
Explore expense tracking and the key benefits of implementing it. Also learn how to set up expense tracking in a PSA tool effortlessly.

Move your service delivery into the fast lane

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.