Question: Who gets paid to challenge your company’s value proposition and keep you competitive? 

Your Sales team? Your prospects? I’m going to tell you why the real answer is “nobody”, and how a new organizational perspective can change that answer to instill a sense of urgency within your customers.

Nobody Cares About Challenging You

Prospective clients have little incentive to challenge you unless they’re mitigating risk. Pushing you to do better on rates, integration, deal structure… those aren’t challenges, just negotiations. Instead, the prospects who would tell you “I feel safer with the do-nothing alternative”, or “I’m not comfortable championing this upstream“, often clog up your marketing and sales pipelines with inactivity because the risk mitigation is right there in their internal dialogue. Any time spent talking to you about it is polite at best.

Now, if your client-facing leadership is typically navigating the negotiation obstacles, the sales pitch will inevitably evolve to focus there. A 28-cell battlecard on competitor pricing, of course. Five slides on integration capabilities, why not? But the question remains: who in your organization gets paid to say, “you know what, most of our prospects will never get this granular because our core pitch hasn’t done the job of making them uncomfortable with doing nothing.“ 

The person making that statement is simultaneously arguing with their client team’s (potentially misinformed) real-world feedback and their product team’s (potentially misguided) hard work. Speaking up like this is a great way to obliterate one’s job security, which is why internal challengers rarely stay afloat once they surface. It’s about personal risk mitigation, after all.

Enter, The Challenger In Residence (CiR)

Forget the staffing cost for now… I’ll give you some alternative offers you can’t refuse later on. Just consider what’s been said thus far: save for rare occasions, there’s neither incentive nor safety in challenging your org to activate their sleeping giant-sized market capture opportunity. And that’s precisely why it needs to be a line-item investment.

You probably already have a CiR waiting in the wings (think, who is it for your team?) — a product visionary in search of new motivation, a commercial power hitter who can’t seem to find the perfect fit on your team, a rising SDR/BDR who is ready to go from commodity prospects to strategic — and with a sprinkle of leadership coaching, this person could become a staple of your competitive strategy, as well as helping to align sales & marketing toward pipelines that actually flow.

There’s no limit to the value that could be unlocked by giving a cross-functional team member carte blanche to unearth and address the tough questions that win (and keep) business. It’s about operationalizing the flashes of opportunity in your business that fizzle without a champion for urgency:

  • The biz dev manager who came over from the agency world because they’ve felt the pain your product alleviates dozens of times
  • The designer who solves industry UX problems for fun, while competitors spend six figures trying to market around the problems
  • The customer success lead who developed a rock-solid ROI formula that has current customers jumping for joy
  • The sales engineer who took enough lunch meetings to notice an underlying thread of technical uncertainty, and has subsequently made the last 3 deals a breeze to close
  • The operations manager who routinely steps into projects and expertly frames up the trade-offs between effort & outcomes to maximize the team’s efficiency

Adopting The CiR: Comfort At Any Commitment Level

To be sure, hiring a CiR means embracing a culture of constant improvement and low egos. Most good companies want that in their culture, but a cross-functional hire has to help build that plane as it takes off. So, how might you commit to a CiR today, without fronting 6 figures’ worth of risk?

Trial A Fractional CiR Role. Budget: low 5 figures ($20,000-$40,000/year). Open a part-time gig up internally and see your SMEs, sales trainers, CS veterans, or even business advisors vye for the title. Offload some of their core work (perhaps with a part-time hire, or an approval of that one vendor they’ve been requesting for months) and see how their freedom of movement changes discussions, creates alignments, etc. Worst case scenario, this person should be able to produce a roadmap for making the role more impactful in the future and documenting its challenges.

Customer communities. Budget: 4-5 figures ($5,000-$20,000/year). Depending on how involved your customers already are, diving deeper here is a no-brainer. Unlike your prospects, current customers have at least some vested interest in your mid-to-long-term success, especially if they can influence the direction. A few one-off events or roundtable discussions are guaranteed to be revealing, and could very well justify more investment toward a permanent in-house resource tapping these wells.

A next-gen FAQ platform (e.g. SkillBuilder): 3-4 figures ($100-$1,000/year). What move could you make today with minimal commitment, which could also place at your feet the very questions and oversight a CiR would be producing? A platform empowering your own team members to become challengers productively. Consider a next-gen FAQ platform to be a challenger-focused knowledge base, if you will.

In the case of SkillBuilder, you can mitigate the traditional drama and cost around “who’s going to manage this knowledge base” via our platform’s AI assistant combined with our collaborative UI. It’s a low-lift opportunity to produce stronger pitches and assets tomorrow, while laying the runway for a Challenger in Residence to generate massive lift once your org is ready to fly.

Is that a convincing reason to try SkillBuilder? If so, you know what to do. If not, tell me why, and I’ll owe you a favor.

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