Challenger Selling Style: Which Sales Tools Help You Close Deals?

Olin Hyde
February 12, 2019

Is the Challenger Selling Style right for you?

There are many different types of selling methodologies: the Challenger Sale, SPIN Selling, Conceptual Selling, SNAP Selling, Sandler Sales, and Customer Centric Selling – to name just a few. While each has their own benefits and challenges, each style has something to offer B2B sales reps to improve conversions and build customer loyalty.

Of course, it’s not possible to use all these selling styles and be successful. You have to choose one style and go with it. So it’s important to study the different types of selling and then decide which style is right for your company—a selling style that fits your company’s goals and culture.

Whether you’re new to the Challenger approach or are part of sales teams that are already using it, there are tools available that make this B2B sales model even more powerful.

I was recently at a sales seminar at ToutApp’s offices in San Francisco where one of the speakers Roderick Jefferson, a sales legend from Oracle, said that The Challenger Sale was hands down the best book he had ever read on selling.

This is high praise indeed from a top authority. So I wrote the name of the book down and read it. Here are some of my key takeaways after reading The Challenger Sale, and the tools I recommend to really make this style work for your business.

What is the Challenger Sales Method?

If you’re not already familiar with the Challenger Sale, we encourage you buy and read the book – it’s full of valuable insights and advice. (I listened to the whole book on Audible while cycling.) In the meantime, here is a high-level view of the Challenger Sales Method.

  • Challenging customers’ thinking. Develop a deep understanding of your customer, and learn to push their thinking.
  • Know their market. Teach your customer something new about competing within their market.
  • Re-framing. Learn to re-frame the way a customer thinks about your category of solution.
  • Control the conversation. Learn to stay in control of the sales conversation, and when to gently apply pressure.
  • All products and services. The Challenger Sales Methodology will work for most industries, but for the complex large scale business sale, it’s even more vital.

3 Tools to Clinch the Challenger Sale

Like most selling styles, success in Challenger Selling requires solid B2B data and top performers. Here are the tools that deliver the goods:

1. LeadCrunch

For most challenger reps, the first question that comes to mind with this method is: “Who do I approach?” You want to approach relevant contacts at companies that are the right fit for your products or services. Before you do the work as a relationship builder, you want to be clear about your potential customers.

LeadCrunch provides the best tool for Challenger Sales on the market – finding the right contacts at the right companies. Using a combination of your own customer data, high-quality B2B data sources, bot crawlers, artificial intelligence and machine learning to deliver the targets that are the best fit for your company – and much more likely to convert to a sale.

You’ll have greater success with Challenger selling if you know their market, and can re-frame your solution if they’re already a good fit. As part of our service, we can contact the businesses for you, so you only receive warm leads. (View the LeadCrunch case studies for specifics.)

2. Charlie

Understanding your customer is much easier when you have a better sense of who they are. Charlie combs through 100s of data sources and automatically sends you a one-pager on all prospects before you meet with them. You’ll have much greater insight on their background and point of view, and be that much better prepared for the sales conversation.

3. Hubspot

Challenging customers’ thinking is a key facet of this sales methodology, so you have to be thinking deeply about the issues they’re facing and have thought leadership in this area. Hubspot allows you to create and syndicate content in an automated fashion. Establishing thought leadership helps you develop credibility with prospects and makes it much easier for you to push their thinking.


The Last Word on Challenger Selling – Keep At It

No selling style is easy, and the Challenger Sales Methodology isn’t either. It requires a lot of you – this style of selling isn’t for everyone. However, particularly for reps selling complex large scale products or services, being able to teach the customer something new about competing in their market can be almost invaluable to sales growth.

That said, if you’ve got Challenger reps who can really master this style, it will boost your sales team’s performance dramatically and take your company to the next level.

What will you do right now to better adapt your approach to be in line with the Challenger Sales method?

Further Reading

Lainey Mebust
July 10, 2020
Lainey Mebust
June 24, 2020
Lainey Mebust
November 22, 2019