What is a Challenger Seller?

Everything you need to know about The Challenger Sale

Happy Cycle to Work Day Day! The only thing better than biking to work is not going to work at all. Shoutout to all the sales reps that commuted to the office this morning. 🚴 

In today’s Follow Up:

  • Breakdown: The Challenger Sale 👀 

  • Sales in the news 🗞️

  • Sales weapon of the day 🛠️

  • LinkedIn Influencers & Memes 🖼️ 

Sales Fact of The Day

Sales leaders believe 50 percent of the clients they speak with aren’t a good fit for the product or service they’re selling.

Source: Sales Insights Labs

What You Need to Know about “The Challenger Sale.”

The Challenger Sale is up there with the classics.

If you work in B2B sales, I’m willing to bet you’ve heard about “The Challenger Sale” before.

The book is written by Matthew Dixon and Brent Adamson and was released in 2011. It quickly rose to the top of best-seller list, and was recommended by sales managers everywhere.

But when you’re too busy making dials and closing deals, you don’t have time to read 242 pages.

So that’s why we’re here. To give you the 2 minute low-down on everything you need to know about The Challenger Sale.


The authors interviewed 6,000+ sales reps across 90+ companies for research on this book.

They observed the characteristics of top-performing sales reps to build a guide for other salespeople.

The Big Idea:

The authors found that every salesperson falls into at least 1 of 5 personas:

1. The Hard Worker ⚒️ 

The hard worker is undeniably motivated. But they’re a lot like the dude who hits the gym every day but still rocks a dad bod.

They work hard and do everything they’re supposed to - make 100 dials, set a ton of meetings, and will even pick your kid up from school if it comes to it - but they don’t challenge the customer’s thinking. They aren’t truly interested in solving the problem for their customer.

The effort to close deals is there, but the results? Not so much.

2. The Lone Wolf 🐺 

The Chuck Norris of your sales team.

You throw em’ into your lineup and they crush quota on their terms.

They’re difficult to manage and aren’t a team player, but hey, you don’t need to spend any time mentoring them.

Put these players on your work-from-home plan and get out the way. But don’t expect them to lead a sales team or mentor the new reps.

3. The Relationship Builder 🤝 

The relationship builder is your classic B2B sales rep.

This rep is focused on building relationships both internally with teammates, and externally with prospects. Their focus on relationships transcends the selling process. Which is both a good thing and a bad thing.

On the good side: They establish excellent rapport and provide great customer service that builds long-term trust.

On the bad side: They don’t challenge their customers and will avoid confrontation.

The relationship builder can be successful but out of the top sales reps, only 7% are relationship builders.

4. The Problem Solver ❓️ 

This rep is always reliable and focused on how they can solve problems for the customers, as well as their internal team.

They’re great at breaking down complex problems and finding the solution.

The downside?

They’re generally reactive, waiting until a problem arises to act. They struggle to create additional value or convince customers of needs they aren’t aware of.

5. The Challenger 🗣️

As you already know, this is the persona the whole book is written about.

As the name suggests, a challenger rep will challenge their prospects to uncover their problems and tailor their pitch to bring them the most value.

This rep isn’t afraid to discuss pricing and get’s the prospect to think about the issue from a new perspective.

You can remember this with the 3 T’s framework:

  • Teach something valuable and new to the prospect.

  • Tailor the sales pitch to their specific needs.

  • Take control of the conversation (pricing, value, etc.).

Most salespeople are relationship builders or a mix of a few personas.

But among the top sales reps, over 40% use the challenger method (according to this book).

Becoming a challenger sales rep is not something that is comfortable for most people. You’ll deal with tension, pushback, and most likely some awkward moments.

At the end of the day, your job is to provide your prospect with as much value as possible and the challenger method can be a great framework to do this.

What Type of Sales Rep Are You?

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Sales Tip of The Day

Are you getting ghosted by a prospect after they say they need to talk to their boss?

Try utilizing your manager or senior leader!

Ask them to email your prospect or prospect’s manager, asking for an update.

Senior leaders can help put urgency on the response and shows the prospect that there are more eyes on the deal.

Sales in the News

  • Salesforce releases their “Sales Elevate” product that will allow sales reps to view and update their pipeline directly in Slack.

  • This sales rep quit her sales job to buy a pink ice cream van, and now earns enough to work three days a week.

  • Three ways that philosophy can help you in B2B sales.

  • Outreach sells Sales Hacker back to the original founder and lay’s off 5% of its staff.

Sales Weapon of The Day

Signaturely: Simple, legally binding e-signatures for documents and contracts (with a free option).

A word from our LinkedIn Influencers:

Hope ❌ Discount ❌ Digital Transformation ❌ 

Sales Meme of the Day

And that’s a wrap!

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