The Monoculture of Enterprise Sales

Why Sameness is the Real Risk in the Age of AI

I used to take it personally. More than once I was passed over for senior sales positions at some of the biggest technology firms in the world. On paper, the explanation was always tidy: I hadn’t carried a quota for a decade.

In practice, the decision had less to do with capability than with a checklist approach to hiring. If you hadn’t been closing deals in the previous 18 months, you weren’t considered a contender.

Yet the irony was hard to ignore. The same companies that dismissed me for their sales teams regularly engaged me for their marketing, communications, sales enablement, and executive strategy work. I was trusted to shape the very narratives their account executives would take into the field, and to brief their leadership teams on market positioning and buyer dynamics. The gap between who they hired and who they listened to was striking.

For a while I assumed geography played its part. Being based outside the major metros can be a disadvantage in global hiring cycles. But over time it became clear that the deeper issue was the industry’s rigid view of experience. Ten years without a direct selling role was enough to disqualify me in their eyes. Yet much of what I saw, and continue to see, suggests that this obsession with uninterrupted sales tenure doesn’t produce the best results. Especially when most candidates come from the same closed pool of vendors, all selling variations of the same magic product.

This is more than just a personal frustration. It’s a structural blind spot in enterprise technology sales. One I see play out every day in buyer advocacy and frontline sales conversations. And it looks increasingly outdated in the age of AI.

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The enterprise tech industry has long prized tenure above all else. Job ads for senior roles rarely ask for adaptability, perspective, or an ability to navigate new categories. They ask for “10+ years of enterprise sales experience.” That phrase has become shorthand for credibility, even when the experience itself comes from running the same playbook at the same handful of vendors.

The result is a kind of recycling. Oracle hires from SAP. Salesforce hires from Oracle. Microsoft hires from Salesforce. Everyone is moving the same people around to sell slightly different variations of the same platform. It creates a talent pool that is deep in process familiarity, but often shallow in originality. These are professionals trained to sell what is already accepted, not to introduce what is still in question.

I’ve seen this up close. The best enterprise technology sales leader I ever met didn’t come from tech at all. They came from the fine arts. Their ability to frame ideas, command a room, and build trust outstripped anything a quota-carrying veteran could teach. More importantly, their approach to team development transformed an entire region’s sales culture. The acolytes who learned under them carried that influence forward for years, changing not just numbers but the way sales was practiced.

And the greatest account executive I ever worked with? They started as a retail sales assistant at Sportsgirl, with zero IT background. What they brought to the role wasn’t product familiarity. It was empathy, resilience, and an instinct for customer needs that no technical résumé could match.

These aren’t quirky exceptions. They’re reminders that the qualities that truly move markets often sit outside the narrow definitions of “experience” that hiring managers or LinkedIn AI recruitment algorithms cling to.

Selling in a mature ERP or CRM market is one thing. The product category is understood, the buyer knows what’s at stake, and the sales process is designed to remove friction. But when the category itself is shifting, as it is now, with AI moving from a buzzword to a platform, the old model looks less like discipline and more like inertia.

The question is no longer “who has carried a quota longest?” It’s “who can carry a conversation when the product is still being defined?”

That question matters most in the age of AI. No one has twenty years of AI sales experience. At best, a handful of people can point to a decade of working adjacent to machine learning or data platforms, but the idea of a career-long AI sales veteran is a fiction. The field is too new, too fluid, and too undefined.

Which means the hiring filters that worked for ERP and CRM fall apart here. A twenty–year Microsoft sales executive doesn’t automatically know how to sell an agentic platform, because there is no standard playbook to follow. The buyer isn’t looking for a familiar checklist. They’re trying to make sense of an unproven future. In that kind of market, credibility doesn’t come from longevity. It comes from the ability to frame uncertainty, to translate technical possibility into strategic clarity, and to build trust where no baseline exists.

And there’s another challenge for the veterans. Their success was built on selling into buying centres that no longer look the same. ERP and CRM were CIO- and CFO-centric motions, with clear procurement playbooks and predictable cycles. But AI doesn’t sit neatly in those lanes. Its impact cuts across HR, operations, customer experience, risk, even frontline service delivery. The buying conversation is migrating outward into parts of the enterprise where yesterday’s gurus never operated, and where their credibility is thin.

This is why the AI shift is not just about products. It’s about people. It should reset the very definition of sales experience. Those who thrived in a world of fixed categories may find themselves out of step. Those who can bridge strategy, relationships, and emerging capability may find themselves in demand, even if they never carried a quota in the “right” years.

So what actually matters when the playbook is gone? Not years in a territory, but the ability to read the room when the room itself is unsettled. Not how many quotas you’ve hit in the past, but how well you can navigate a buyer’s uncertainty today.

The most valuable skills now are relational and interpretive. The ability to build trust quickly across technical and executive audiences. The discipline to translate architectural shifts into business outcomes. The confidence to acknowledge risk while still creating momentum. And perhaps most of all, the willingness to learn in public because in AI, both the buyer and the seller are learning as they go.

This is where many “non-traditional” profiles have an edge. Strategists, advisors, solution consultants, business analysts, and those who have worked at the seams of marketing, product, and sales enablement in non-IT sectors often know how to shape a narrative, connect stakeholders, and create clarity. These aren’t necessarily the skills or domain of the quota-carrying IT veteran who’s mastered discounting and procurement cycles. They’re the skills of someone who can sell a future state that hasn’t yet been proven.

The irony is that the very qualities once seen as disqualifiers, things like time away from the field, careers built adjacent to direct selling, may be the ones most suited to leading the next era of enterprise sales.

As ERP titans pivot toward agentic, AI-first platforms, I don’t think the next generation of sales leaders will emerge from the same recycled talent pool. They will come from unexpected places: strategists, storytellers, or those who’ve led in functions adjacent to sales. People who can hold the room when the product is still foggy, who can translate uncertainty into belief, and who can shape narratives about a not-yet-defined future.

And here’s the irony. In most corners of corporate life, monocultures are seen as a liability. We celebrate diversity of thought, background, and experience in boardrooms, product teams, and marketing departments. Yet in enterprise sales, a monoculture is still treated as a virtue. The same résumés are shuffled around, the same playbooks re-run, the same assumptions reinforced. In the shift to AI and agentic platforms, sameness isn’t safe. It’s the real risk.

The leaders who will matter most won’t be carbon copies of yesterday’s quota carriers. They’ll be the ones who break the pattern, who arrive without the perfect résumé but with the ability to carry the conversation when the product, the market, and the future are all still being written.