B2B Sales Tips

The Challenger Sales Rep: The Ultimate in B2B Sales Tips

There are a number of B2B sales tips floating around the web, but it is often difficult to discern the helpful from the gimmick.
Here’s an amazing stat to ponder: 53 percent of B2B customer loyalty is a product of how you sell, not what you sell. This knowledge completely flipped the script on how to sell effectively. In Matthew Dixon and Brent Adamson‘s best-selling book, The Challenger Sale, they’ve outlined how to take advantage of this fact and become a more effective salesperson. In this blog post I’ll outline the three elements that make up a successful ‘challenger sales rep’.


Introduction: Challenging the Status Quo

In doing their research with CEB (now part of Gartner), the authors first identified five “types” of sales reps: the hard worker, the relationship builder, the reactive problem solver, the lone wolf, and the challenger. There was a clear winner and loser profile, while the other three were in the middle.
Based on the five profiles, they identified that the best reps were most often in the challenger profile, and to my surprise, the relationship builder profile had the lowest ranking. While relationship builders are generous with their time and are loved by the customers for building rapport and sincerely seeking to understand their customers’ situations, they simply don’t get the results that the challenger does. You could say that the relationship builder wants to be accepted into the customer’s ‘comfort zone’, while the challenger is adept at pushing their customer out of his or her ‘comfort zone’. Of the forty-four attributes they studied, the ones that defined a sales rep as a challenger were the following:

  • Offers customers a unique perspective
  • Strong two-way communication
  • Knows the value drivers for the particular customer
  • Is comfortable discussing money
  • Can pressure the customer

Put another way, they are able to teach, tailor and take control.


What sets challengers apart is their ability to teach their customers something valuable. Where the relationship builder dives into knowing their customer, the challenger takes the next step, already knowing the customer’s context and providing them a unique perspective on their business, giving them insights that goes beyond simply explaining the product.
When surveying happy purchasers, elements that stood out about the rep were that they were providing insight and ongoing consultation, along with navigating landmines and education on the issues. This can be done under the umbrella of “commercial teaching”, but it’s not enough to just be a trusted adviser. That advice and education needs to lead to “wins” in terms of sales. To do this, commercial teaching follows four rules:

  1. Lead to your unique strengths: Your going to show how you’re outperforming your competitors on those things you’ve taught your customers that are most important.
  2. Challenge their assumptions: you want to frame your teaching, so they react with a “Huh, I never thought of that before”: focus on reframing their views instead of telling them what they already know. You want them thinking, “what else don’t I know that Randy can teach me, and what does this mean for my business?”
  3. Catalyze Action: You can build an ROI calculator, but it has to go beyond just your product ROI and towards the ROI built on the re-framing you just led them to.
  4. Scale Across Customers: It’s best to segment customers by need or behaviour, and not always geography size or industry to be able to scale what you’ve done with one customer with others.

With these rules in mind, it’s possible to choreograph insight-led conversations. They don’t happen by accident. It may mean shaking up your sales pitch deck, more quickly establishing your understanding of your buyer’s context, reframing the situation, giving them the numbers (also called rational drowning), making an emotional impact (making sure the customer sees themselves in the story you are telling), outlining the new way, and presenting your solution. Further, the challenger model is BOLD:

  • Big over small with regards to scale
  • Outperforming over achievable with regards to risk
  • Leading-Edge over following with regards to innovativeness
  • Difficult over easy with regards to implementation

You’re asking them to see things from a new perspective. In turn you have a solution that perfectly fits that new perspective.


It’s not enough to “reframe” or sell one person on this new perspective. With the average B2B buying decision involving 5.4 people, this means talking to more people to get a deal done.
The challenger rep understands the need to tailor the message: how the different stakeholders fit into the business, their roles, what they’re worried about, and what they want to achieve. The rep then doesn’t focus so much on what he or she is selling, but what the person they’re speaking to is trying to accomplish. To do this, they focus on customer outcomes: the goal in need of improvement, the metric of measurement, and the magnitude of impact.
While this work of tailoring might seem tedious, it is usually the same stakeholders with a similar profile across any industry you are tailoring your solution to. Procurement is looking for one set of answers, IT another, and Finance something else. The sales rep can develop a score-card which will help them with tailoring and personalizing the “win” for each member of the team they are reaching out to and help them better talk their language.

Taking Control of the Sale

Three misconceptions are outlined in the book, to help the reader better understand what taking control of the sale means.
Misconception #1: Taking control is Synonymous with Negotiation
Taking control doesn’t just happen at the end, in the negotiating process, but right from the beginning. The challenger presses for contact with the key stakeholders, pushing for expanded access to decision makers from the beginning. As well, rather than sitting back and letting the buyer execute the process of a complex sale, they teach the customer how to buy the solution. I’ve had the experience of asking a potential buyer, “what would be the process of bringing my solution to the decision makers in your team” and being met with a blank stare because they did not know the process. I’ve found it better to take control, and suggest a process.
Misconception #2: Reps Take Control Regarding Only Matters of Money
Challengers need to push their customer not only around money, but around ideas, because they are moving them towards a reframe that won’t simply be accepted automatically. When a customer pushes back, asks more questions, or states that his or her company is “different”, this is the dialogue that helps the challenger move the conversation forward. They can take control and bring new ides to the table. This is critical because as the reframe is established, it paves the way for the solutions you will provide to be connected to those ideas.
Misconception #3: Reps Will Become Too Aggressive if We Tell Them to “Take Control”
When the relationship builder’s goal is to please the customer, this can lead to passive behaviour leading them to do things not in the best interest of their company. The goal is not the opposite, however, found in aggressive behaviour (attacking others, or using antagonistic language). Instead the goal is an assertive rep who is constructive and communicative, even if they’re using strong language. While reps are asked to “sit on the customer’s side of the table”, it shouldn’t mean giving them whatever they want.
The challenger allows a certain amount of tension and ambiguity when working through and addressing aspects of a deal, not rushing to the close. The book further lays out game plans that can be developed, giving the rep clarity of direction, and adding value through the commercial teaching process which will help them have courage and more assertiveness through the buyer’s journey.


At the heart of the challenger method is a focus on commercial teaching, which brings greater insight to the buyer than they previously had, leading to a willingness to continue the buying process with key stakeholders, who see their needs and goals addressed.
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The Challenger Sales Rep: The Ultimate in B2B Sales Tips