The Challenger Conundrum: What If Marketing Isn’t Up to the Challenge?


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You want to become a Challenger Rep®, but your company’s marketing organization is not supporting your personal aspiration. Houston, we have a problem.

Reading between the lines of the The Challenger Sale (authored by Matthew Dixon and Brent Adamson of Corporate Executive Board or CEB), a sales rep acting alone faces almost insurmountable odds of becoming a Challenger Rep. Marketing’s strong support is an essential prerequisite for transitioning a sales rep into a fully-credentialed Challenger Rep. According to CEB, “Challenger Reps are made, not born”. “Challenging is about organizational capability, not just rep skills.” To reinforce the “organizational capabilities” messaging theme, CEB walks the talk and offers a provocative insight directed squarely at the marketing organization. “It’s one thing to tell reps ‘Be a Challenger’. It’s another thing altogether to tell them exactly what you want them to do.”

A Challenging Conundrum

You’ve read The Challenger Sale , and on your own, made the decision to drink the Challenger Kool-Aid. Or perhaps your manager has told you to “just go out and do it, be a Challenger”. Your company may have even officially embraced the Challenger Sales Model and kicked off a multiple-year implementation journey recommended by CEB.

But you observe a potential problem: your company’s “organizational capability” to support a Challenger implementation is weak or worse yet, missing altogether. Your marketing and product groups are stuck in a rut spewing out product-centric collateral and late-to-the-buying-process leads which do little to support a true Challenger transformation.

Instead what you need from marketing are a series of “commercial teaching pitches” and “provocative insights” that could help you deliver tailored customer conversations that will change how your customer thinks about their business and ultimately your company’s solutions. If you are a territory rep, you need these teaching pitches and insights to be scalable and repeatable across a customer segment defined by need. And, if you are a named-account sales executive (or a major/strategic/key account manager), you need customer-specific teaching pitches and provocative insights – not generic one-size-fits-all insights. After all, your named-account customer deserves, and expects, sophisticated customized insights and perspectives.

You face a challenging conundrum; what’s an aspiring Challenger Rep to do?

Be Assertive and Take the Lead

Challenger Reps are, by their nature, assertive. If your marketing organization isn’t currently up to the challenge of helping you become a Challenger Rep, I recommend you take the lead. Resist the temptation to whine and complain. Instead, re-direct your energy to more constructive actions that will move you closer to achieving your personal goal. Consider this temporary roadblock a personal challenge, a test of your discipline and creativity. Challenger Reps are tenacious; they constantly push customers (as well as their own company colleagues) to think and act differently. Use this situation to practice Challenger skills and behaviors.


1. Form a team – Four eyes are better than two and six eyes are better than four. Find at least three other like-minded colleagues to informally join you on this journey. One of them should be a well-respected sales colleague who best exemplifies the skills, knowledge, and behaviors inherent in a Challenger Rep. Another team member should be recruited from the marketing organization, products group, or sales enablement team. Your marketing organization as a whole may not be providing the right support, but there is a high likelihood that a true ally is sitting somewhere amongst their midst. The third team member is crucial: someone from your finance organization who thoroughly understands the financial benefits of your solution and who is recognized as an advocate of your sales organization. In my experience, all finance organizations have these sales support superstars. You need a financial person on the team to help you elevate the financial content of your commercial teaching pitch.

2. Select a target account and identify priorities – Resist the temptation of starting with your solution and how you articulate its business benefits. Instead, first select a target account. Conduct research and identify the company’s emerging business initiatives. Then, solve backwards to identify the solution(s) that will help them accelerate their business outcomes.

3. Select an under-appreciated solution – Identify a relevant solution(s) that is generally misunderstood and undervalued in the marketplace. The attributes of this solution create competitive differentiation, but your customers don’t fully recognize its uniqueness and value at this point in time.

4. Craft a commercial teaching pitch – Get creative and leverage your team members for this critical step. Craft a unique company-specific insight and point of view that the customer likely hasn’t heard before from your competition. Incorporate a strong financial element to your insight and point of view. Outline a conversation guide that demonstrates your customer acumen and factually supports your point of view. If done well, the customer conversation, when executed, will eventually lead to the under-appreciated attributes of your solution.

5. Practice, test, and implement – Practice delivering the commercial teaching pitch as a fluid customer conversation, not a formal presentation or a deadly interview. Use role play simulation and story-telling techniques, and make it real. Try it out on internal colleagues; get their reaction and refine it. Then, implement it in the field with your target account.

6. Document and socialize – Document the process and customer reaction and share this information with your sales and marketing organization. Encourage others to join your effort to become a Challenger rep. Create a central repository of example unique insights, commercial teaching pitches, and best practices.

Republished with author's permission from original post.

Jack Dean
As co-founder of FASTpartners LLC, Jack brings extensive technology buying experience as a Fortune500 Chief Financial Officer to the B2B technology sales training industry.He has facilitated client-sponsored business acumen training for 15,000 B2B technology sellers representing 150 global technology companies.Participants in Jack’s business acumen training have produced directly-attributed revenue of over $1 billion (in the 3 months after training) and training engagement ROIs averaging 500%.


  1. Very important points, and a nicely pragmatic solution.

    Sales people have felt forced to reinvent sales tools – or create them from scratch – because of marketing’s perceived inadequacies for ages. They have seen it as just part of getting their job done, and, as we know, nature abhors a vacuum. The demands of a “Challenger Selling” environment throw these deficiencies into sharp perspective.

    In a perfect world, you’d hope that marketing “get it”, and the ultimate goal of any organisation has got to be to get sales and marketing on the same page and eliminate the need for these field-level guerrilla operations. But needs must, and Jack has come up with an approach that at least gets multiple eyes – and multiple experiences – focused on developing and delivering a field-level solution.

    This article also clearly shows that “Challenger Selling” can’t be accomplished simply by putting sales people through a training course, and that you first need to get your story straight before you equip and teach your sales people to tell it.

  2. Bob, thanks for your thoughtful comment. As we both know, sales people don’t live in a perfect world where sales and marekting are always synched-up. As you say, the demands of a “Challenger Selling” environment magnifies any disconnects. Someone usually takes the lead, gets the story (value-based messaging) straight, and sets the pace in the marketplace for others to follow. In situations where marketing isn’t yet up to the Challenger challenge, I see this as unique opportunity for individual sales superstars (and want-to-be superstars) to lead by example. With success, marketing will run to catch up.


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