What Customer Success Managers can learn from “The Challenger Sale”

Brooke Goodbary
7 min readSep 30, 2017

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“The Challenger Sale” has been one of the most popular and influential sales books since it was released in late 2011. And while it’s been primarily marketed towards sales reps and managers, I was struck by the valuable lessons it can provide Customer Success Managers. The core arguments from the book that can be applied to Customer Success teams are:

  • Challenge customers
  • Change the status quo
  • Deliver solutions to problems

Challenging customers

Let’s take a moment to consider how we arrived at this point- why was a new sales model necessary in the first place? In the traditional IT buying process (think early 2000s) sales reps held all the information. If a prospective customer wanted to learn more about a company’s products or services, they had to talk to a sales rep who acted as something of a gatekeeper. In this world Sales often had the upper hand in their dealings with customers. One of the lasting shifts towards a SaaS sales model is that information became commoditized. Prospective customers are now able to get details about a company’s products or services from their website and can even occasionally get a pricing quote. In the modern software buying process, the customer has the power.

Move past consultative sales by teaching customers something new

The role of sales reps in this new customer- centric landscape has been forced to evolve. If customers can easily Google a list of the top 5 mid-market CRM solutions and compare and contrast their feature sets, what value does a sales rep provide? This has gaven rise to the consultative sales approach. In a consultative sales model reps aim to be seen by prospective customers as a consultant, offering advice and education on how their product can be applied to address the customer’s problems. Although a lot of companies were successful with this sales model for a time, many struggled on the follow-through. Sales reps focused on elements of the sale that didn’t prove impactful to the long-term success of the customer- such as relationship building or reactively solving problems that came up during the sales process. These actions handicapped their companies’ ability to push customers towards realizing long-term value from their products.

Surveys have consistently show that customers assign the highest value to salespeople who make them think, bring new ideas, or find creative and innovative ways to help their business. In recent years, customers have been demanding more depth and expertise. They expect salespeople to teach them things they don’t already know.

How does this translate from Sales to Customer Success?

While teaching and education are a big part of the sales process, they’re also a fundamental part of Customer Success. Challenging how a customer does business isn’t a one time event- over the course of the relationship it will be the CSM’s job to continuously challenge how the customer is receiving value from their product. To help customers continue to find value, CSMs need to shift from a consultative tone and adopt a challenger approach- this is the core lesson Customer Success Managers can learn from “The Challenger Sale”.

Changing the status quo

No doubt about it, changing the status quo is hard. You have to overcome the powerful momentum for people to continue doing things the way they have always been done. In order to change the status quo CSMs need to sell the vision of a better way forward for the customer. It’s not about how great your product is, it’s about how much better the customer could be by adopting your solution to their problem.

“You’re asking customers to change their behavior — to stop acting in one way and starting acting in another. To make that happen, however, you have to get customers to think differently about how they operate. You need to show them a new way to think about their business.”- The Challenger Sale

Is it possible for a customer to see value without changing the status quo? It’s possible, but unlikely. The issue with tacking your solution onto an existing workflow or process is that it probably won’t be integrated into how the company does business. An add-on product can easily be removed without causing major disruption. And if your Sales team is teaching customers a new way to address an existing problem, it’s probably going to take more than a haphazardly applied solution to fix it and for your product to meet or exceed everyone’s expectations.

Ask hard questions

One way to change the status quo is to ask hard questions that challenge the customer to think about their problem in a different way. Part of the process of teaching customers something new is asking them to consider the current state of their business. The point of posing these questions is not to get an immediate “yes”, it’s to get something closer to a “huh, I never thought of it that way before.” Example: Cold-call sales strategies that push for an early yes (ie. “Do you have a desk? Well most people who have desks need chairs, and I sell the most comfortable chairs in town”) don’t allow you to develop the depth that is necessary to really change someone’s point of view.

Get stakeholders onboard

Few things can torpedo the success of a project like a combative stakeholder. Selling a vision to one project manager or team isn’t enough, you need widespread support to change the status quo. Stakeholders often want to see enthusiasm among the rank and file before they adopt a new way of doing business- this is one of the reasons bottoms up sales strategies have received so much attention). Which means that the solution you propose should appeal to end users and executives alike. Does your solution have the potential to save your customer $1MM a year through improved efficiencies? Entice the end user by touting the 10 minutes per day it will save the average employee rather than focusing on top line savings. Don’t forget to also build interdepartmental support. For instance, loop in the head of corporate training to ensure new employees are being onboarded to your product. Purchasing decisions are more decentralized than ever, but don’t assume you bypass key stakeholders if you want to make a lasting change to the status quo.

Delivering solutions to problems

Remember, customers don’t really care about your product, they care about their problem. Your product is a means of addressing that problem and this is the job your product has been “hired” to do. After asking hard questions you should know what your customer’s goals and objectives are. You should know how they will be measuring success or failure, and have agreed on what steps need to be taken to achieve these goals.

“Your customers aren’t buying a technology. They’re buying a solution to a problem, a path to a better way. It’s your responsibility to understand the customer’s goals and objectives and steer the customer along that path.” — Nello Franco

Now comes the hard part- delivering on those goals.

Leverage your company’s unique benefits

A key element of the Challenger Sale model is that companies need to identify and articulate the unique benefits of their product. Customer Success teams need to be ready to make good on delivering the benefits pitched during the sales process. Arming CSMs with content and best practices that they can call upon when talking to customers increases the likelihood that Customer Success teams are able to provide value to customers at scale. Incorporating your company’s unique benefits into these materials empowers CSMs to focus on long-term gains that will benefit both the customer and the company.

Know what it means to be “customer-centric”

Let’s get this out of the way- being “customer-centric” doesn’t bending to a customer’s every whim. To actually be a “customer-centric” company you need to teach your customers a new way of addressing their problems through your products. The difficulty lies in presenting a vision for their business that is compelling enough to change the status quo. Anything short of this will prevent them from seeing long-term value from your products.

“There are several ways to be “customer-centric” that are actually bad for business… [one is] assuming an order-taker posture with the customer (i.e., taking short-term orders when the customer is pushing for them, instead of getting the customer to think about longer-term business)” - The Challenger Sale

“The Challenger Sale” presents Customer Success teams with new strategies to deliver long-term success to their customers. Contrary to popular belief, it argues that challenging your customers (instead of catering to them) produces more value. Changing the status quo and delivering value happen within the context of this challenge based relationship. One final word of advice- challenging customers does not mean being rude or adversarial. Teaching a customer something new should not be done in a condescending or know-it-all tone. Asking hard questions shouldn’t feel like an inquisition. Showing customers respect is still table stakes. But that doesn’t mean that being passive to their every need and opinion is how you produce value. There are numerous lessons Customer Success Managers can learn from “The Challenger Sale”- namely that challenging customers to realize the vision they had for your product is a key part of Customer Success.

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