Your biggest enterprise deals don’t move through a funnel. They move in a W.

The board meeting usually follows the same script.

Growth is behind plan. The pipeline looks thin. Two or three big enterprise deals have been stuck in the same stage for another quarter. Then someone says the obvious thing:

“We need to hire more salespeople.”

The CEO nods. The head of sales nods too, even though they know it probably will not work. Recruiting takes four months. Onboarding takes six more. Eighteen months later, revenue has barely moved, and the same two or three people are still the only ones closing the company’s biggest deals.

I have seen versions of this pattern across hundreds of companies, from small startups to Fortune 500 enterprises. The diagnosis is usually wrong.

These companies do not have a headcount problem. They have misunderstood the shape of the sale.

For most established enterprise categories, the sale looks like a funnel. A team defines a need, compares vendors, narrows the list, and recommends a winner. That works when the buyer already knows the category exists.

But the biggest new-category deals do not move through a funnel. They move in a W.

Salesforce did not just sell CRM. It sold a new way to buy software.

The easiest way to see the difference is to look at the B2B companies that changed their markets.

Salesforce did not become Salesforce by behaving like just another CRM vendor in a procurement bake-off. In 2000, the company launched with a message built around “the end of software.” That was not a feature claim. It was a category claim.

At the time, large companies were used to buying enterprise software as installed systems: licenses, servers, long implementation cycles, and heavy IT involvement. Salesforce had to sell a different belief first: that customer relationship management could be delivered through the internet, as a service, without the old software model.

That kind of sale does not begin with procurement comparing three familiar vendors. It begins when someone senior enough to care about speed, cost, and business agility decides the old model is worth challenging.

Workday faced a similar problem in HR and finance. It was not enough to say it had better software. It had to convince large organizations that core systems of record, the sensitive systems that run payroll, people data, and financial management, could move to the cloud.

Snowflake had to make a similar argument in data. Its early promise was not simply “a better database.” It was that the cloud would allow a different architecture for data warehousing, data sharing, and analytics.

Okta did the same with identity. It was not selling another login tool. It was helping companies accept identity as a cloud-based control plane for a world of SaaS applications, remote workers, and distributed systems.

HubSpot’s early growth came from a different kind of category argument. Its founders saw that buyers were changing: people did not want to be interrupted by ads; they wanted useful information. Before HubSpot could sell software, it had to sell the idea of inbound marketing.

These companies had different products, different buyers, and different markets. But they all had to win the same first argument: the buyer had to believe the category mattered.

That argument is almost never won at the bottom of the organization.

A normal enterprise sale starts low. A new-category sale starts high.

Imagine the buyer as a skyscraper.

At the top are the owners, board, CEO, CFO, CIO, and senior executives. Below them are business-unit leaders and VPs. Below them are directors, managers, analysts, specialists, and procurement teams.

When a large company buys something from an established category, most of the work happens in the lower and middle floors. The category is already understood. Nobody needs to persuade the CEO that payroll systems, CRM tools, data warehouses, IT service desks, or collaboration software exist. The buyer only has to decide which vendor is best.

That is the sale most enterprise salespeople are trained to run.

A new-category sale is different.

The buyer often has no budget line for what you sell. There may be no specification, no purchasing process, and no internal owner. Procurement cannot run a process for a category the company has not yet decided it needs.

That is why many scale-ups lose before they are ever properly evaluated. They start too low.

They meet with analysts, managers, technical specialists, innovation teams, and procurement contacts. These people may be smart, curious, and generous with their time. They may ask good questions. They may even like the product.

But they usually cannot create a new category inside the company. They can evaluate a sanctioned category. They cannot sanction one.

For that, the seller has to start higher.

The biggest deals move in a W

A new-category enterprise deal usually has five movements.

First, the seller anchors the idea with a senior sponsor. This is not a product demo. It is a strategic conversation about a problem the company already knows it has and a new way to solve it.

Second, that senior sponsor delegates the idea down into the organization. A team is asked to evaluate whether the promise is real.

Third, the middle of the organization reports back up. This is one of the most important moments in the deal, and the seller is usually not in the room. The evaluators have to make the case internally.

Fourth, leadership decides the idea is worth a real process and sends it back down again, often to procurement and a different group of stakeholders.

Fifth, the familiar vendor comparison begins. Requirements are written. A shortlist is built. Vendors are compared on function, risk, price, and fit.

That is the W: up, down, up, down, and back toward a decision.

Many scale-ups enter at the fifth movement and mistake it for the whole sale. By then, the most important work may already be over.

If another vendor created the category conversation at the top, armed the middle with the right internal argument, and shaped the requirements before the formal process began, it will be very hard to beat them with a better RFP response.

The sale often happens in a room you are not in

The most dangerous part of a new-category sale is the moment when the evaluator has to explain you to their boss.

This is where many promising deals quietly die.

The middle-management team may have spent weeks with you. They may have seen the demo, spoken to references, read the material, and agreed that the product is interesting. But “interesting” is not enough.

They need to walk upstairs and make a defensible argument.

Why this? Why now? Why should the company create budget for a category it has not bought before? Why is doing nothing more expensive than acting? Why is this not just another tool?

If the evaluator cannot answer those questions without sounding like your salesperson, the deal stalls.

This is what category creators understand.

Salesforce made “software as a service” a boardroom-level argument about speed and simplicity, not just a CRM feature comparison. Workday made cloud HR and finance a strategic architecture decision, not just an HR software swap. Snowflake made data infrastructure a cloud transformation discussion, not merely a database benchmark. Okta made identity a security and operating-model issue, not just an IT admin convenience.

In each case, the company had to give internal champions language they could repeat upward.

The seller’s job is not only to persuade the people in the room. It is to equip them to persuade the people outside the room.

A pitch deck is rarely enough. The champion needs ammunition.

The Stephan trap

The only personal example I need is the one I think of as the Stephan trap.

In almost every large account, there is someone like Stephan.

Stephan sits several floors below the decision-makers. He has deep technical knowledge, genuine curiosity, and a willingness to spend time with new vendors. He answers emails. He asks thoughtful questions. He schedules follow-up calls. He may even become an internal fan.

He will also never buy anything.

I have seen scale-ups spend six months building a relationship with Stephan and call it enterprise pipeline.

Stephan is real. Stephan is useful. Stephan is not a deal.

If your only contact inside a major account is two or three levels below someone who can create budget, you do not have a sales opportunity. You have a research project you are running for free.

This is not Stephan’s fault. He may be doing exactly what his company wants his to do: learn, compare, gather information, and keep vendors occupied until the organization has a reason to act.

But a new-category seller cannot confuse access with authority.

A meeting is not momentum. Curiosity is not sponsorship. Activity is not a deal.

Bottom-up adoption still needs top-down sanction

Some founders object to this because they have seen product-led companies grow from the bottom up.

That is true. But it does not disprove the W. It often confirms it.

Slack is a good example. Many workers first experienced Slack at the team level. It spread because people liked using it. But when Slack moved into large, complex organizations, the company still needed an enterprise motion. Enterprise Grid exists because large companies need security, governance, administration, compliance, and structure.

The same pattern shows up in developer and infrastructure companies.

Datadog can start with engineers who need better visibility into cloud systems. But as usage expands, the buyer changes. What began as a monitoring tool becomes a platform discussion involving engineering leadership, security, operations, finance, and sometimes the CIO.

Atlassian products often entered companies through teams that simply wanted better ways to track software work. But once usage spreads across departments and business units, the conversation changes. It becomes an enterprise standardization discussion.

Product love can create the first opening. It does not always create budget, governance, or enterprise-wide commitment.

That is why the W still matters. Bottom-up adoption may get you into the building. It does not guarantee you can move up the building.

This is why hiring more salespeople often fails

When growth stalls, boards and CEOs often assume the sales team needs more capacity. In established categories, that can be true. If the market understands the category and the company has a repeatable process, more good reps can mean more revenue.

But in new-category enterprise sales, the bottleneck is different.

The company is not short on people who can run calls, manage opportunities, or respond to RFPs. It is short on people who can create executive urgency where no budget line exists, guide a buyer through internal uncertainty, and help champions make a case in rooms the seller cannot enter.

That is a rarer skill.

In my experience, only a small minority of proven enterprise salespeople can make that shift consistently. Many excellent reps are trained to compete inside known categories. They are good at discovery, qualification, demos, procurement, pricing, and negotiation.

Those skills still matter. But they are not enough.

New-category selling requires a different kind of pattern recognition. The seller has to know whether the deal is still being sanctioned, whether the middle has enough confidence to vouch upward, whether procurement is running a real process or a theater process, and whether the company has an executive reason to act.

That is why so many scale-ups remain dependent on one or two rainmakers.

The uncomfortable truth is that the biggest deals are often closed by a very small group of people. Everyone else sells smaller things, supports the process, or works opportunities that were never truly alive.

Hiring five more people who can only run the bottom of the W does not solve that problem. It adds cost, burns time, and creates a larger pipeline that still depends on the same few rainmakers to close.

The category creators built more than sales teams

The most successful B2B category creators did not scale only by hiring more account executives.

They built systems around the sale.

Salesforce had a message simple enough for executives to remember: the end of software. HubSpot turned inbound marketing into education, vocabulary, content, certification, and community. Okta helped make identity a board-level security conversation. Snowflake made the Data Cloud into a strategic idea that could travel beyond the data team. Slack created an enterprise product for the governance questions that appear only when a collaboration tool moves from teams to global companies.

The common lesson is not that every company needs a bigger marketing department or a better slogan.

The lesson is that category creation requires infrastructure around the rainmaker.

A rainmaker running a major new-category deal is not simply “owning an account.” They are orchestrating a political, financial, and strategic process across a large organization.

They have to identify the senior sponsor. Understand the business problem. Translate the product into executive language. Equip mid-level champions. Track the internal decision path. Stay close when procurement enters. Manage competing stakeholders. And do all of that across a deal cycle that can last six to eighteen months.

One person can do that well on a small number of accounts. Stretch them too far and quality drops. Deals drift. Better-known competitors win because they are easier to buy.

So the answer is usually not to manufacture more rainmakers. Most companies cannot do that quickly, if at all.

The answer is to build leverage around the rainmakers they already have.

That means better stakeholder mapping. Better account intelligence. Better executive messaging. Better material for internal champions. Better visibility into where each deal actually sits in the W. Better support from marketing, sales development, product, and leadership around the few people who can truly move the largest accounts.

In other words, stop asking rainmakers to carry the entire enterprise motion alone.

If a company has only two people who can consistently win the biggest deals, the question is not how to replace them with ten average enterprise reps. The question is how to make those two people effective across more of the right accounts without diluting the work that makes them successful.

What CEOs should ask before approving another sales hire

Before approving another senior sales hire, CEOs and boards should look at the stalled pipeline differently.

Do the biggest opportunities have a senior sponsor?

Has that sponsor delegated the idea down for serious evaluation?

Can the middle-management team explain the case internally without relying on the seller?

Has leadership sent the deal into a real process, or is procurement merely collecting information?

Are the company’s rainmakers involved early enough, or are they being pulled in only after the decisive conversations have already happened?

Those questions will reveal more than another forecast meeting.

A stalled enterprise deal is often not stuck because the salesperson failed to follow up. It is stuck because the company is trying to run a funnel when the buyer is moving in a W.

Before hiring another rep, ask a simpler question: which of your stalled deals has an executive sponsor, a mid-level champion, and a mandate to run a real process?

If the answer is “none,” you do not have a hiring problem.

You have been mistaking activity for a deal.