Table of Contents
Guide reps to process adherence with Challenger Sales templates
See how
Or use our free web app.

How to Close Complex Sales with the Challenger Sales Process

Guide reps to process adherence with Challenger Sales templates
See how

Common advice for today’s sales professionals typically sounds something like this: “Put the customer first.” “Let your prospect control the pace of conversation.” “Listen to what your lead needs, then make recommendations.”

Our current sales environment revolves around relationship-building, customer-centricity, and viewing sales as a consulting role rather than a revenue-building stream. It assumes the customer doesn’t want to hear a sales pitch and would rather have a supportive resource willing to lay out all their options — even their competitors.   

And while this kind of sales methodology has its place in the business world, relationship-building isn’t a golden ticket to success. It’s time-consuming, emotionally taxing, and doesn’t guarantee a payout.

For top-performing sales reps, in particular, customer-centric selling could actually make selling harder.  

In situations like these, the challenger sales model could be the key to unlocking a more efficient sales process

What is the Challenger Sales Model? 

In their book The Challenger Sale, Brent Adamson and Matthew Dixon outline five types of sales reps that exist within sales teams: 

  • The Hard Worker Driven, self-motivated, and always looking for ways to improve. 
  • The Lone Wolf High-performer, confident, but not necessarily a team player. 
  • The Relationship Builder Patient, people-first, positions themselves as an advocate for their prospect. 
  • The Problem Solver Focused on finding solutions and solving problems. 

And finally…

  • The Challenger Takes control of the conversation, doesn’t shy away from uncomfortable talking points, and focuses on teaching the prospect. 

The Challenger sales rep recognizes that their prospect might not always know the best option for them and pushes them to think about their challenges or opportunities from a different perspective. They’re ready to (respectfully) go toe-to-toe with the prospect and won’t shy away from a productive debate. 

Challengers are typically high-performing sales reps with deep knowledge about their prospects, industry, challenges, and opportunities. They’re able to find flaws in their prospect’s way of thinking and challenge their assumptions or beliefs in ways that are educational and insightful. 

The best way to understand the Challenger sales type is to compare it to the Relationship Builder (the rep type most of today’s sales tactics are geared toward). In both instances, the rep assumes the customer is capable of doing their own research and coming to their own conclusions about what kind of product or solution they need.

But where the Relationship Builder wants to position themselves as a consultant, advocate, and source of support for the prospect — someone to answer the questions the prospect comes up with throughout their research — the Challenger wants to push them to get out of their comfort zone and recognize where their research might be flawed.

The Challenger is still a source of knowledge and support, but steers far away from becoming a “yes man.” 

When to use the Challenger sales process? 

The Challenger sales process works best in complex sales environments when prospects may feel particularly overwhelmed or confused about their options.

But adopting the Challenger sales method can be difficult for a sales team. Because the methodology is aggressive and contentious in nature, implementing it in a way that is still respectful and supportive can be a delicate balance that is hard for sales reps to achieve.

If reps push too hard, come across as arrogant, or don’t know when to back down, it could tarnish their (and the company’s) reputation. 

For the Challenger sales approach to be successful, reps need to be experts in their industry, know their prospects' business inside out, and know how to present solutions that are educational, informative, and insightful. 

How to get started with the Challenger sales process 

Here are the steps you need to follow to get started with the Challenger sales process.

1. Warm Up: Get to know the business

The very foundation of the Challenger sales model is to debate. In order to do so effectively, the sales rep needs to be well-versed in the challenges and opportunities facing their potential customer's business.

Where other methodologies let sales reps get away with a quick Google search or LinkedIn scan before making a phone call, the Challenger method requires reps to know all the ins and outs of the industry or business so they can find loopholes in their prospects’ way of thinking. 

Sales reps who specialize in specific types of businesses or industries will do best with the Challenger sales methodology because they can really dig deep into the problems their potential customers are facing. 

Here are some ways to develop a deeper industry understanding: 

  • Customer conversations Every time you take part in a customer conversation, listen closely to the pain points they mention. It’s likely those issues are felt across the entire industry.
  • Industry publications – Get your information from the same sources as your prospects. Subscribe to popular industry publications and follow industry leaders on social media.
  • Competitor materials – Know what resources and information your prospects are probably reading. Check out case studies, ebooks, and other sales materials your competitors are providing so you know which talking points you might need to debate.

By the end of this stage, sales reps should have a thorough understanding of the prospect’s challenges and the solutions they're considering.

2. Reframe: Find a new perspective

The next step of the Challenger sales methodology is to encourage the prospect to think about their problem or challenge through a different lens. In other words, it’s time to reframe the problem. 

Here’s an example. 

Let’s say that during the warm-up phase of the process, you learned that a prospect is struggling to scale their business. They’ve concluded that in order to grow more efficiently, they need better project management software to keep track of all their moving pieces and ensure nothing slips through the cracks. 

But based on your experience working with similar customers and your knowledge of the industry, you know the prospect’s actual problem isn’t with getting things done on time — it’s that they need to get more done in less time. They don’t actually need a project management system; they need automation. 

During the reframing phase, you’d explain the flaws in the prospect's logic and show them why automation is actually a better solution. Your goal isn’t to sell a specific product (that will come later) but rather to get the prospect thinking about the solution in a new way. 

Use data and evidence to back up your claims, and avoid giving a product pitch. The prospect should feel like they’re being shown a new way of doing things — not like they need to buy your particular product to get the outcome you’re promising. 

Here is one way you could reframe this situation to your prospect: 

“Properly managing your projects and tasks is a great way to stay organized, but it will only marginally improve your team’s productivity if they’re already operating at their maximum. I can show you some examples of companies that still struggled with scaling even with proper systems and management in place.” 

3. Connect: Use emotions to build personal value 

While we like to think sales is all about logic and data, making purchasing decisions is actually quite emotional. Empathy goes a long way when trying to close a deal. 

At this stage, it’s all about making an emotional connection with your prospect — connecting beyond the data and facts. 

Using the same example situation as the previous phase, that conversation might look like this… 

“Scaling a business puts a tremendous amount of stress on you and your team. Properly organizing and managing the many moving parts of your business’s growth can relieve some of that pressure, but without additional support, your team is at risk of burning out.

This happens to a lot of companies when they reach the stage you’re at — they focus so much on the bottom line that they forget to take care of the people working for them. If your team starts to feel overwhelmed or unhappy in their roles, you risk losing great people.

Improving organization and project management will only do so much. To truly scale efficiently, you need something more.”

Your goal is to make as much of an emotional impact as possible, but try to do so in a way that connects back to your prospect’s initial challenge. For example, if they’re concerned about their budget, try to paint a picture of what they’ll be able to do with the money they save.

Or, if security is their biggest worry, explain the consequences of not taking enough caution with their data. 

4. Imagine the future: Selling the value proposition 

Up until this point, the goal has been to get the prospect to see their challenge the same way you do. Now you’re ready to dive into how they should actually solve their problem. While we’re still not ready to pitch your product, you want to start painting a picture of what their future could look like if they listen to your advice. 

Here’s what that conversation would look like using our example: 

“You need a solution that helps your team get more done in less time. If you’re able to take some of those repetitive, boring tasks off your team’s plate, they can stay focused on the work they enjoy doing — so even as you grow, your team stays engaged and fulfilled. And you can do this without hiring additional team members!”

Think about selling the solution of your product rather than the product itself. What benefits will your prospect realize if they choose to buy from you? 

The idea is to get the prospect to buy into the outcome first. When they can envision themselves in an idealistic future, they’ll be more open to hearing your product pitch — meaning the overall conversation can flow with less resistance.

5. Pitch: Showcasing the product  

The final step is the sales pitch. While this step is pretty straightforward, you want to make sure you’re tying the offer back to the points you’ve already discussed up to this point.

Here’s an example: 

“You need a solution that does more than just manage the little tasks your team needs to complete. You need a way to automate them. By streamlining the repetitive or boring tasks on your team’s plate, you free them up to focus on the work they actually like.

Projects flow more smoothly, you can keep your staff at their current level, and you can improve their job satisfaction. On top of all of that, you can increase productivity and your bottom line. Scaling will become much more efficient.

With our automation software, you can easily create your own automations and integrations without coding experience.” 

This is a great opportunity to offer a free trial, a product demo, or a walkthrough of what you’re offering.

Closing complex sales with the Challenger sales model 

When used correctly, Challenger selling is a way to stand out. While other sales reps are focusing on the long game, this methodology gives sales reps an opportunity to take control and have meaningful, productive conversations.

This method of selling does take practice, but don’t let it intimidate you. With the right research and a solid understanding of the industry your prospects work in, it can turn good sales reps into great sales reps.

Use the tips we outlined above to adopt the Challenger sales methodology today.


Weflow is the fastest way to update Salesforce, convert your pipelines, and drive revenue.

More articles by

Related articles

Top 17 Sales Methodologies You Need to Know

All the best sales methodologies in one place.

The Complete Guide to Sales Qualification

Learn everything you need to know about qualifying leads in our handy guide to sales qualification.

Conceptual Selling: What You Need to Know

Learn how to use conceptual selling to improve sales efficiency and build better customer relationships.

Baseline Selling Explained: What You Need to Know

Find out what Baseline Selling is and how you can get started.

The Full Guide to NEAT Selling

Read our guide to get started with the NEAT selling framework.

Your Guide to Target Account Selling

Target account selling fills your sales funnel with high-value leads. Here's how to get started.

CHAMP Sales Explained (incl. 23 Qualification Question Examples)

Learn what the CHAMP sales methodology is and how to get started using it.

Question-Based Selling: Everything You Need to Know

Check out our guide to get started with question-based selling.

Strategic Selling Process: What it Is, How to Use It & Examples

Strategic Selling builds long-term relationships with the entire company — not just one contact. Here’s how to use it.

Value Selling Framework: What it Is and How to Use It

Everything you need to know about value selling frameworks, how they work & how to create your own. FREE questions PDF.

A Complete Guide to the Gap Selling Framework

Everything you need to know to get started with the Gap Selling framework.

An Inside Look at SNAP Selling: The Four Basics (+Checklist)

Find out how SNAP selling works and why you should use it.