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

    Bob Apollo
    Post by Bob Apollo
    October 26, 2015
    The Challenger Conundrum: What If Marketing Isn't Up to the Challenge?

    As regular readers will know, I’m a great fan of the principles set out in the best-selling “The Challenger Sale”. But there’s an unspoken difficulty: what if the smarter members of the sales team “get it”, but marketing is not yet ready or able to support the initiative. Do you have to admit defeat, or wait for things to change? Not necessarily...

    I’m delighted to introduce a guest article by Jack Dean, co-founder of FAST Partners, who confronts the issue head-on - and offers some highly practical advice about what to do next. The article was originally published here. Over to you, Jack, and thank you for your permission to share this:

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

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

    The Challenger SaleReading between the lines of the The Challenger Sale (authored by Matthew Dixon and Brent Adamson of 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."

    About Jack Dean: Jack is the co-founder of FASTpartners, a sales training company focused on helping sales and marketing professionals gain customer executive sponsorship, influence investment decisions, and accelerate customer business outcomes and financial performance.  A former Fortune 500 CFO, Jack has over a decade of experience working with sales and marketing professionals to improve their business/financial acumen, customer acumen, and executive selling skills.

    Thanks, Jack! I hope that you’ve enjoyed his practical perspective. For more information on FASTpartners, go to or contact Jack at And if you've got your own perspectives or experiences on how best to adopt Challenger Selling in your own organisation, please share them here.

    Bob Apollo
    Post by Bob Apollo
    October 26, 2015
    Bob Apollo is a Fellow of the Institute of Sales Professionals, a regular contributor to the International Journal of Sales Transformation and Top Sales World Magazine, and the driving force behind Inflexion-Point Strategy Partners, the leading proponents of outcome-centric selling. Following a successful corporate career spanning start-ups, scale-ups and market leaders, Bob now works as a strategic advisor, mentor, trainer and coach to ambitious B2B sales organisations - teaching them how to differentiate themselves through their provably superior approach to achieving their customer's desired outcomes.