The most dangerous sentence in enterprise sales is "Don't worry, I'll handle it internally."
Your champion means it when they say this. They're enthusiastic, they believe in your product, and they genuinely intend to push it through. The problem isn't their commitment. It's that enterprise purchasing decisions don't get made by one person — no matter how senior that person is.
Josh Squires, SVP of Strategy at Bongo, said something that stuck with me: deals are rarely killed because of a solution's quality. More often, it's because the business case can't survive all the rooms you're not in. That's the sentence I wish I'd heard five years earlier than I did.
What single-threaded actually costs you
When your entire deal runs through one person, you're exposed in ways that aren't obvious until it's too late. Your champion may not have budget authority — they can recommend, but someone else signs off. They might change roles or get pulled onto a different priority. Or they might just get busy with their actual job and your deal quietly drops off their list. I wrote about this as the first warning sign of a stalling pilot — when your main contact goes quiet, it's almost never because they stopped caring. It's because something else became more urgent.
There's a harder version of this too. Albert Vazquez-Agusti calls it "Innovation Theater" — pilots that exist as a concept car for your champion's internal optics. They're running the pilot to demonstrate that they're forward-thinking, not because they're building a business case for a purchase. You're helping someone pad their innovation credentials. That's not a deal. It's a side project.
I'm not saying most champions are doing this. Most are trying their best. But even the best champion is just one person, and enterprise deals require more than one person's conviction.
The four people in every enterprise deal
Martin Roth has a stakeholder map that I've found to be almost universally accurate. He identifies four roles that show up in every enterprise purchasing decision. I've started thinking about every pilot in these terms.
The Champion. This is your internal advocate — the person who brought you in, who believes in the product, who's willing to put their name on the recommendation. They matter enormously. But they rarely have purchasing authority on their own, and they're often mid-level enough that their recommendation needs reinforcement from above and below.
The Technical Buyer. This person cares about implementation, integration, security, and whether your product is going to create problems for their team. Their job is to not get burned. They don't need a sales pitch. They need honest answers to hard questions: what's the implementation timeline, what breaks if something goes wrong, how does it handle our existing stack. If you never talk to this person, they become a blocker at the last minute — and last-minute technical objections kill deals that were otherwise done.
The Economic Buyer. This is the person with the budget. They're spread thin across twenty initiatives and they don't have time for a product demo. What they need is a clear ROI story — ideally on one page — that answers a single question: is this worth the money? If your champion is the only person making this case, and they're doing it from memory in a hallway conversation, the economic buyer's answer is usually "not right now."
"Hidden Hillary." This is the one that gets you. Hidden Hillary is the phantom influencer who may not want your deal to succeed. Maybe they backed a competitor in an earlier evaluation. Maybe your product automates something their team does manually, which threatens their headcount. Maybe they just don't like change. You often don't know Hidden Hillary exists until she's killed the deal — a quiet "I have concerns" in a meeting you weren't in, and suddenly the whole thing is "under further review."
I had a deal once where everything looked perfect. Champion was enthusiastic, technical evaluation went well, the numbers were strong. Then it went silent for three weeks. When I finally got the real story, someone in a completely different department had raised a concern about data residency — a legitimate issue, but one we could have addressed in fifteen minutes if anyone had told us. By the time it surfaced, the buying window had closed. That was a Hidden Hillary.
How to multi-thread without going around your champion
This part requires some care, because the last thing you want is for your champion to feel like you're going over their head. The best approach I've found is to be direct about it.
Ask your champion: "Who else needs to be comfortable with this for it to get approved?" Most champions will answer honestly — they usually know who the other stakeholders are, and they're often relieved when you offer to help engage them. They feel bad about the slow progress too, and they want support.
Offer to do the work yourself. "I can do a 15-minute technical overview for your security team so that doesn't become a blocker." "I can put together a one-page ROI summary for your VP — would that be helpful?" You're not circumventing your champion. You're making their job easier.
Create materials your champion can forward without scheduling a meeting. One-pagers, ROI calculators, security questionnaires, integration documentation — things that let the deal sell itself in rooms you're not in. The best enterprise salespeople I know think of every document as a proxy for a conversation they can't have in person.
And get the economic buyer a single touchpoint early. Even one 20-minute meeting changes the dynamic completely. The deal goes from "something my team is looking at" to "something I've personally evaluated." That's a different category internally.
When a growing stakeholder list is progress — and when it's a warning
Sometimes new stakeholders appearing mid-pilot is a good sign. It means the deal is moving through a real procurement process with real reviewers. I wrote about this as Sign 3 in the stalling-pilots post — a growing list of stakeholders who need to weigh in.
The test is simple. Are new stakeholders reviewing with a timeline — "the security review needs to be done by April 15th" — or reviewing without one? The first means the machine is working. The second often means nobody wants to own the decision, and adding reviewers is a way to defer it.
Help your champion — but don't depend on them
The best thing you can do for your champion is make the deal easy to approve in every room, even the ones you'll never see. Arm them with the right materials. Engage the stakeholders who can block the deal. Get ahead of Hidden Hillary before she gets ahead of you.
Your champion got you in the door. That matters. But closing the deal takes more than one person's enthusiasm. It takes a business case that survives every conversation on the way to a signature.