When people discuss The Challenger Sale, the focus usually lands on the five sales rep profiles:
The Hard Worker
The Challenger
The Relationship Builder
The Lone Wolf
The Reactive Problem Solver
The most surprising takeaway? The Relationship Builder—often the most likable and service-oriented rep—was the lowest-performing in complex sales. Meanwhile, The Challenger was the highest-performing, with over 50% of star reps fitting this category.
That revelation alone makes many business owners and sales leaders rethink their hiring approach and redefine what “top talent” looks like in their organizations.
The Challenger Difference
What makes a Challenger different?
According to The Challenger Sale authors, Matthew Dixon and Brent Adamson:
“A Challenger is defined by the ability to do three things: teach, tailor, and take control.”
Most sales leaders stop there and think, We need to hire more Challengers.
But there’s a critical, often-overlooked piece:
“Many organizations assume that the migration to the Challenger Selling Model is a question only of improving individual rep skills. For the model to really work, that is emphatically not the case. This journey is actually just as much about building organizational capabilities as it is about developing individual skills.”
Sales Performance vs. Sales Enablement
When I started my business nearly a decade ago, almost every engagement began the same way:
“My salesperson isn’t performing. Can you evaluate them and tell me if they’re any good?”
After spending just a few minutes with the salesperson, the real issue became obvious.
They weren’t necessarily failing because they lacked skill or effort. In many cases, they were failing because they weren’t set up for success:
Ideal client profile lacks clarity
Prospect list is scattered and unfocused
Messaging is undifferentiated and lacks value
Sales process is inconsistent and unstructured
Performance expectations are vague or undefined
Whether they were “good” or not didn’t matter in the long run—without the right foundation, they had little chance of succeeding.
And they certainly weren’t equipped to sell like a Challenger.
Building a Challenger Sales Organization
If you want your sales team to teach, tailor, and take control, you can’t leave it up to them to figure it out alone.
Teach: Create Scalable, Repeatable Insights
“Building a teaching capability is not something you want your individual reps out there figuring out on their own.”
“The business issues you teach customers to value must be scalable and repeatable, and as such, must be created by the organization.”
Equip your team with the right framework, structure, and questions to educate ideal customers and demonstrate expertise.
Tailor: Help Your Team Customize the Message
“The organization is responsible for helping salespeople tailor their messages to each customer’s industry and company context.”
“The organization must identify which teaching messages will resonate with which stakeholders.”
Provide a clear ideal client profile, key stakeholder personas, and value messaging so salespeople can personalize their approach effectively.
Take Control: Empower Your Team to Lead the Sale
“Salespeople armed with powerful teaching messages produced by their organizations will be in a much better position to take control of the customer conversation.”
“The organization must equip reps to identify and properly engage with the right stakeholders on the customer side.”
Establish a repeatable and effective sales process so salespeople can confidently take and maintain control at every stage.
The Challenger Sale: A Blueprint for Sales Leaders
The Challenger Sale is one of the most impactful books I’ve read in my 20+ years in sales. It forces you to rethink what makes a great salesperson—and how to build a high-performing team.
The takeaway? Growth starts with you.
Tailor → Refine your sales strategy
Teach → Demonstrate expertise through insightful questions
Take Control → Establish a repeatable sales process with clear success benchmarks
Where to Start: The Revenue Compass Assessment
If you want to build a Challenger sales team, you need to first identify your sales organization’s bright spots and bottlenecks.
The Revenue Compass Assessment helps you evaluate your sales strategy, process, structure, and management to pinpoint exactly where to focus your efforts.
Go Deeper:
Or check out my new book: Beyond the Founder Rainmaker - Build Your Blue Chip Sales Strategy