We asked two sales leaders where reps should take over from AI

AI can handle account research, outreach sequencing, and even first-touch conversations with buyers.

What's the moment in a deal where a human rep becomes irreplaceable — and what happens if they're not ready for it?

Stephen Higgins

Sr. Sales Director - HubSpot

The moment a buyer stops evaluating your product and starts evaluating whether they trust you with their problem.

AI can do a lot of the heavy lifting to get you to that moment faster — better research, sharper outreach, cleaner sequencing.

But you can't prompt your way out of a prospect leaning in and saying, "We've tried this before, and it didn't work."

That's where reps either earn the deal or lose it quietly.

The risk I see isn't AI replacing reps.

It's reps getting so comfortable with AI handling the early work that they stop sharpening the skills that matter in that moment: discovery, trust, navigating real objections.

AI gets you to the conversation. The rep still has to win it.

If they're not ready for that, you're just generating more qualified losses.

Keegan Otter

Co-Founder - Warmly

The full scoping of the contract.

AI might have the data, but it lacks the EQ to ask challenger-type questions that surface deeper pain.
You also need humans for contracting and negotiation — no buyer wants to talk price with AI or ask it for custom packages.

That requires a layer of human trust.
A buyer would want an actual person to walk them through what a package's cost covers and work with them to put certain terms in place.
Building confidence, negotiating terms and packaging, and getting a contract signed are all best guided by human touch.
If a rep isn't ready for that, they should be able to ask discovery questions to get there — almost like a whole loop around.