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The Challenger Sale: The Seller That Cares

Updated: Apr 2


What is a Challenger Sales or Seller

What is the meaning of The Challenger Sale?


The Challenger Sales methodology is a customer-centric approach that focuses on delivering unique insights and value to the buyer throughout the sales process. Rather than simply responding to the customer's needs, the Challenger seller takes control of the conversation by:

  1. Teaching: Sharing valuable insights and perspectives that challenge the customer's current thinking and highlight new opportunities or potential risks they may not have considered.

  2. Tailoring: Customizing their message and approach to resonate with the specific customer's unique situation, goals, and challenges.

  3. Taking control: Guiding the sales conversation in a direction that leads the customer to the desired outcome, while maintaining a two-way dialogue and addressing their concerns along the way.

The Challenger seller deeply understands their customer's business, industry, and objectives. They leverage this knowledge to constructively challenge the customer's assumptions, simplify complex ideas, and demonstrate how their offering can help them achieve their goals in a way that sets them apart from the competition.

Adopting this proactive, insight-driven approach, the Challenger seller positions themselves as a trusted advisor and partner rather than just another vendor. This methodology aims to create value for the customer throughout the buying process, ultimately leading to improved customer loyalty, higher win rates, and more profitable, long-term relationships.


The Five Profiles of Sellers:


5 Profile of a Sales Person
5 Profiles of a Seller

  1. The Hard Worker: Always goes above and beyond, doesn’t give up easily, is self-motivated and likes feedback and development but may take the harder route to get things done (every good new salesperson should start here)

  2. The Relationship Builder: Builds strong customer advocates, generates customer loyalty, is generous with giving their time to help others and gets along with everyone. This individual can have difficulty with saying no and setting expectations.

  3. The Lone Wolf: Self-driven, not so much a team player. Follows their own instincts, and is self-assured, autonomous and independent. The lone wolf profile may struggle with delegating and orchestrating larger and more complex deals with a desire to "own all parts" of a sales cycle

  4. The Problem Solver: Is reliable, ensures all of their customer’s problems are solved and is detail-oriented. Service orientated can have its benefits but more often than not their goodwill can be taken for granted.

  5. The Challenger: Observes their client's world with a lens and degree of empathy, is keen to understand the customer’s business process and operation, loves to debate, and pushes the customer to get out of their comfort zone and to think differently. The challenger sets expectations, deadlines and outcomes and can identify when their time is not needed, wanted or appreciated to quickly refocus.


Key traits of a Challenger:


What is a Challenger Sale?
What is a Challenger Sale?
  • They excel in teaching customised approaches by understanding the customer's business and offering a unique perspective. These experts engage in effective two-way communication during sales interactions.

  • They craft their message by keenly understanding the customer's situation and strategic priorities and value drivers to influence decisions.

  • In guiding the sales process, they confidently navigate discussions about finances and skillfully influence customers towards a successful sales close. This proficiency sets them apart as challengers in their industry, product or service domain.

"Challengers are made not born"
Challenger Sales infograph
Challenger Sales performance

7 Steps to Become a Challenger Seller:

  1. Preparation: Do the research and groundwork on your target organisation. This means speaking to non-decision-making employees within a target company to help form a thread of common challenges that are concurrent across an entire department or organisation and relate to key strategic priorities

  2. Articulation: It's your job to understand your client's challenge better than they do by helping summarise and simplifying into a clear concise problem statement that rings true to your client's core.

  3. Pain for gain: Be comfortable with being uncomfortable, validate by asking for their business early, often and when you've earned the right to - "but how - I don't want to sound salesy." The truth is, your customer knows exactly who you are and they still accepted the meeting - showing how you are different by being clear about your role and responsibility yet helpful is exactly what your client needs to find credibility and trust to do business with you.

  4. Project equality: Own the room, this is your domain, and the client turned up to hear what you've got to say. Share that you understand their challenge intimately from the prior industry experience or internal research conducted show that you are passionate and confident about solving their pain, and educate them by connecting the dots with inconsistencies and shortfalls to help enhance perspectives on their situation.

  5. Sellers who prepare show that they care: Tailor your message to that industry or department and the specific needs they've been telling you about. Show them you've been listening.

  6. Define your Purpose and Guide on What should happen next: Chances are likely that your prospect is going through this procurement process for the first time entirely or at the company they are procuring on behalf of. Be upfront with your intentions, guide and set the following steps, but talk about them at the beginning of every conversation. E.g. "Today I'd like to take you through how we help [X] industry solve [A, B, C], and by the end of today's discussion, we will be able to validate if this is a conversation worth continuing." It's critical to follow through at the end of your discussion and guide your prospect on what should happen next with firm timelines and actions.

  7. Keeping your client accountable: Our brain processes 60,000 thoughts a day, which means you might make up 1% of a prospect. If you genuinely believe you can help an organisation with your product or service, hold yourself accountable to hold your client accountable. Every sale is made not in front of the client but in the follow-up. Just remember to add value at every touch point and in between.

Challenger Summary:

The Challenger Sale by Brent Adamson and Dixon Matthew is a fantastic book to help you understand the theory of this seller's methodology and mindset. Still, this paradigm shift often comes from experience and unwillingness to be kicked like a tyre as a seller.


Value your time and energy. Focus on working with prospects who want to work with you and how you can add value in between and during every customer-facing interaction so they can do the internal selling on your behalf.


Josh Jebathilak

Written by Josh Jebathilak CEO @ Fruition Services

Josh is a revenue-generating leader with selling experience from top tier Software & Hardware organisations such as monday.com, Zendesk, & SAP



Fruition Services is an end-to-end CRM Software and Sales consulting institution that specialises in scaling the Fortune 500 of tomorrow.


Contact us to see how we can help your Sales Operations come to Fruition.

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