How to keep a B2B deal from getting stuck with HR: keep the CEO in the conversation
To keep a B2B deal from getting stuck with HR, don't let the CEO's handoff be the end of your relationship with the CEO. Take the call with HR, do it well, and at the same time give the CEO a separate, personal reason to stay in the conversation. The one I like best is an invitation onto your show.
When a senior person forwards you down the org chart, they're usually being helpful. They liked what they saw and sent it to the team that handles it. But the deal now lives in a process that wasn't built to say yes quickly, and the person who could say yes has moved on to the next thing in their inbox.
How deals slide down the org chart
On August 3 I was on a weekly call with a founder who builds wellness software for companies. He'd written a LinkedIn post about recovery and mental capacity. A bank CEO commented on it. The founder sent over a report, and the CEO forwarded it to HR. That led to a sales call with the HR team, booked for that Thursday.
That's a great start. A CEO found you through your own writing and engaged publicly. Most founders would kill for that.
It's also exactly how deals die. The CEO was the one who felt the problem. HR is the one who'll evaluate the vendor. HR has a process, a budget cycle, other priorities and a dozen vendors already pitching wellness. The energy that came from the top slowly turns into a procurement question.
Our enterprise page puts it this way: one contact is one point of failure. Your champion goes quiet or changes jobs, and a six-month deal dies with them. In this case the champion hadn't gone anywhere. He'd just handed the deal to someone else and stepped back.
The 60K deal one executive killed
The same founder had a fresh scar that made this concrete. A deal worth about 60K had just fallen through. The reason wasn't price or features or a competitor. The client's boss refused to install an app for employees. One person, above the people the founder had been selling to, said no to the delivery model, and the whole thing was gone.
He didn't sulk. He started building a desktop version so he could go back to that account with something the executive would accept. That's the right instinct. But the deeper lesson is that the person who can kill a deal is often someone you never spoke to.
Put the two stories side by side. In one, a senior person engaged and then handed off. In the other, a senior person nobody had talked to shut the door. Both say the same thing: if you're not in a relationship with the top of the account, you're exposed.
Invite the CEO onto the show
The move we agreed on for the bank was simple. Keep the CEO relationship alive by inviting him onto the founder's podcast.
Think about why that works where a follow-up email doesn't. A follow-up to a CEO who just delegated you says "I'd still like your time." He's already given it, and he's told you where to go. Another ask is easy to ignore.
An invite to the show says "I'd like to feature your thinking." It's about him. It connects to the reason he engaged in the first place, the post about recovery and mental capacity, which is clearly something he cares about. A bank CEO talking about how his people recover and perform is a good episode on its own terms.
And it creates a parallel track. HR runs their evaluation. Meanwhile the founder spends thirty minutes on the record with the CEO, talking about the exact problem the product solves. When HR comes back with questions, the person they report to has a fresh, personal memory of the founder.
You don't use the episode to pitch. You use it to understand how the CEO thinks about the problem, and to be someone he respects. The deal benefits without ever being mentioned.
Running the HR call without losing the top
None of this means you treat HR as an obstacle. That's a quick way to lose the deal. HR will run the program, and they need to want it.
Prepare for the HR call as seriously as you would for the CEO. Learn what they care about: adoption, effort for employees, how it fits their existing benefits, how they'll measure it. Answer those questions well.
Mention the CEO's interest naturally. You're there because their CEO responded to your work. That's context, not leverage. Don't wave it around.
Ask about the path to a decision. Who else is involved? Is there a sign-off above HR? What killed similar programs before? The 60K deal teaches you to ask the delivery question early. If someone senior has strong feelings about installing apps, you want to know on the first call, not the last.
And then keep the CEO track running separately: the invite, the episode, the clips, a short note after. Two threads, two relationships, one account.
Multi-threading as a founder, without a sales team
Big sales teams have a word for this: multi-threading. Get several people in the account engaged so no single person's silence kills the deal. They do it with account executives, sales engineers and executive sponsors.
Founders don't have that bench. You have yourself, maybe one other person, and limited hours. That's why the show matters. It's a multi-threading tool a single founder can run.
Invite the CEO. Invite the head of the department that would use your product. Invite the person who'd champion the pilot. Each episode is a different relationship inside the same account, and each one is a conversation the guest wanted to have.
We built our enterprise page around that idea: everyone who has a say in the deal, from the VPs who own the budget to the directors who feel the problem to the champions who'll run the pilot. The system maps who signs, who uses and who can block, and invites them onto your show.
What to do this week if you've been handed down
If a senior person just forwarded you to someone else, this is what I'd do before the week ends.
Thank them personally and briefly. Tell them you're talking to their team.
Invite them onto your show, connected to whatever made them engage in the first place. Make it about their view, not your product. Keep it to three sentences, and send it today.
Prepare for the delegated call like it's the only call, because for that person it is.
Map who else could say no. If you don't know, ask on the call.
And if the deal has already slipped, it isn't too late. The CEO who engaged once will usually engage again if the reason is about him. An episode invite three weeks after a handoff still lands, because it isn't a chase. It's a compliment.
A deal that lives at the top moves at the speed of the top. A deal that lives in process moves at the speed of process. You get to choose which one you're in.
Frequently asked questions
How do I reach the CEO when I'm handed to HR?
Give the CEO a separate reason to talk that isn't a sales follow-up. An invitation onto your show, tied to the topic that made them engage, keeps a personal thread with the top of the account while HR runs its evaluation.
Is it OK to go over a contact's head?
Going around someone to pressure them usually backfires. Running two honest relationships is different: serve the person you were handed to well, and keep a genuine conversation going with the executive who sent you there.
How do I multi-thread a deal as a founder?
Invite several people from the same account onto your show: the executive sponsor, the head of the team that would use the product, and the likely champion. Each episode is its own relationship, so one person going quiet does not end the deal.