This editorial appeared in the August 7th, 2025, issue of the Topline newsletter.
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Over a decade ago, The Challenger Sale urged a generation of sales leaders to hire differently. In a world where relationship-building was the default, it told us to look for someone else: the rep who taught prospects something new, reframed their thinking, and guided them — sometimes provocatively — to a better future.
“They teach for differentiation, tailor for resonance, and take control of the sale.”
— The Challenger Sale, Dixon & Adamson
As a Founder of a GTM recruitment company in the early days of SaaS, this persona was exciting. It felt revolutionary. But as the SaaS model matured and the cloud became the norm, the Challenger seemed to fade from relevancy. In fact, our team hasn’t had a client reference this specific profile in at least five years. Not because the approach was discredited — but because the market stopped demanding it. Today many revenue teams no longer seek that insight-driven agitator. They prize consensus-builders who can navigate established decision influencers.
So, is the Challenger dead?
Maybe it’s just been dormant. Unessential. Waiting impatiently for AI as a core part of the software stack to bring it back into the zeitgeist.
The Challenger Was Born for the SaaS Revolution
When Salesforce and its early cloud counterparts hit the market, it wasn’t enough to demo the product. You had to sell the idea of SaaS itself. On-premise software was the norm. CIOs feared perceived security and compliance issues of data in the cloud. Procurement teams struggled to value subscriptions. The job of the rep wasn’t just to explain features — it was to reframe how the buyer saw the world.
That’s exactly what the Challenger did best. As Dixon and Adamson argued, these reps were provocateurs. They brought unique perspectives. They introduced cost models, competitive dynamics, or risks the buyer hadn’t yet considered.
In a world of evangelism, the Challenger was king. And GTM leaders who built teams around this profile often outperformed those who didn’t.
Why the Challenger Quietly Faded
Over time, Cloud software went from novel to normal. Subversion waned. Incremental improvements rose. Sales cycles got shorter. Buyers came in educated. Product-led growth and inbound marketing took center stage. In that environment, the rep didn’t need to challenge an existing paradigm — they needed to execute reliably, navigate procurement, and hand off to success teams.
The Challenger persona wasn’t wrong or irrelevant. It just wasn’t as necessary.
Compounding this was a fundamental misunderstanding of what The Challenger was. It became a training guide to improving the processes of existing sellers. Encouraging them to provoke. When I read that book I identified with the profile as core to my own anti-establishment personality. An articulation of why I had enjoyed outsized success in my own sales career. Not something a less curious person could learn in a training environment. This confusion changed it from a hiring profile to a sales process and — I think — weakened a compelling premise.
AI May Reawaken The Beast
Here we are again — in the middle of another seismic shift. AI is changing the way software behaves, delivers value, and interfaces with users. And most buyers are still catching up. They don’t know how to separate marketing hype from practical capability. They’ve been told that AI should improve their organizational efficiency 10% every month, but they’re unsure how to evaluate models, measure ROI, or implement effectively. The desire for AI advantages is high; but how, what and when are very confusing and lead to buyer procrastination.
On the seller’s side, AI companies are still figuring out how to even position value. Providing efficiency improvement numbers or even ROI is tantalizing to potential clients, but individual client workflows and implementation environments are not yet set up to accommodate this kind of seismic shift potential, which leads to increased client turnover. That’s why we are seeing so many AI companies focusing more on “Forward Deployed Engineers” and Post Sales roles in their GTM teams. But FDEs and Solution Engineers are not top of the funnel. Companies need hunters and this is exactly the kind of environment where the Challenger thrives.
To sell AI-enabled solutions, your reps must do more than “show the platform.” They need to:
- Teach buyers about the opportunities of AI in their context,
- Tailor their story to the specific problems and workflows of the prospect’s business,
- Take control of a deal process that can easily stall in uncertainty.
In other words, AI is what cloud was in 2011: misunderstood and massively important. And once again, we need sellers who can lead from the front — not just follow a playbook.
What This Means for GTM Leaders
If you're building a go-to-market team today and you're not explicitly hiring for Challenger traits — you may be missing the moment.
The reps who will win in the age of AI won’t just be excellent communicators. They’ll be subject matter learners. Strategic thinkers. Market translators. People who can navigate ambiguity with authority.
At our recruitment shop, we’ve seen a renewed hunger for critical thinking, business acumen, curiosity, and the ability to synthesize complex technology into business value needs. It hasn’t fully translated back into people saying, “Give me a Challenger,” — but the profile they’re describing sounds awfully familiar.
