Why HubSpot Pulled Their Entire Sales Team Off the Road for AI Enablement

(The Lessons Go WAY Beyond Tech and Tools!)

At a time when many organisations are reducing enablement budgets (the 2026 Mood of the Sales Leader report found businesses slashed 30% from their development budgets), and many are saying they're simply too busy to prioritise enablement, HubSpot did the opposite.

In our REV UP Rebellion podcast, I sat down with HubSpot APAC Lead Enablement Partner Alli Kleppe, who shared that one pilot of their Prospecting Agent is saving in the region of 95% of admin time.

A separate account-sourcing pilot gave reps around 20% of their week back. That's approximately 12 to 15 hours, per person, per week!

And here's a key factor that helped deliver that outcome: leadership led from the front and got behind the AI initiative and it made the difference.

So I got Alli to walk us through it and what we can all learn from their experience.

Important enough to take everyone off the road

To take all sales & GTM teams off the road is a significant commercial call, and it signals how seriously leadership weighted this. A factor Alli believes led to the success is how leadership got behind the AI focus:

"I don't mean just sending an email or opening a Zoom call. It's really being on the floor, paying attention and involved."

The difference in adoption when leaders are genuinely in it is significant.

Before you layer on AI, sort the foundations

One of the most practical lessons Alli shared: you cannot build an effective AI layer on a messy foundation.

The approach was to slow down to go fast. Go back to the foundations first, even when the products being discussed were released six weeks prior. Build it properly and you can scale quickly. Skip it and adoption collapses.

The lessons for all of us is to get our ducks in a row, before layering AI.

The Ferrari in the garage problem

Sellers are carrying 13 or more tools, however most are living in just three of them.

For a successful pilot, HubSpot focused on creating behavioual change by working on the tools sellers are already in most of the time, the CRM. And this isn't just a bias because HubSpot is a CRM provider, it's because it's the one tool sellers spend most of their time in. The success came from meeting the team where they were at.

HubSpot solved this by embedding their sales methodology directly into their CRM instance. On any live deal, sellers can see in real time whether they've covered all elements of the methodology. No tab switching and no re-reading a document. The learning surfaces where the work is actually happening, at the moment it's needed.

Alli calls this "just-in-time learning." The right information, in the right place, at the right time. A relevant case study for the industry the seller is calling into. A one-pager on the products they're likely to discuss. Surfaced by AI, inside the tool they're already in.

The lesson for us: don't just add another tool, see if you can integrate within your existing tools where your sellers are already hanging out.

Around 20% of the week back. What are we doing with it?

That's the real question underneath all of this.

A HubSpot account-sourcing pilot changed how sellers find accounts. The result: approximately 20% of their week back, around 12 to 15 hours per rep. Alli estimates the Prospecting Agent alone is saving in the region of 95% of admin time for that specific task.

But if that time gets swallowed by more meetings and noise, the ROI disappears.

The teams pulling ahead are using that time to go deeper on industry research, customer knowledge and relationships. The things AI genuinely cannot do.

HubSpot measures this through productivity per seller, tracking both activity level (calls and customer conversations) and average deal size. When one goes up and the other doesn't, that's the signal to look at where the gap actually is.

ROI on AI has been notoriously hard to track and measure, HubSpot's defined what success looked like to them, tracked it and took action where needed.

The paradox sitting in the middle of all of this

AI adoption is accelerating, and simultaneously in-person events are selling out in days.

Buyers are craving human connection more than ever. Alli's observation from across LinkedIn, Elmo Software and HubSpot: even as more buyers want a seller-free experience, when they do choose to engage with a person, that interaction now carries more weight than it ever has. Getting it right is the differentiator.

"We have to find that sweet spot where it's AI-informed but human-delivered."

Alli referenced an EY study that found the gap between how companies think their AI interactions land with customers and how customers actually feel them is bigger than most businesses realise. We're not as seamless as we think we are.

The lesson for all of us is continuously monitoring how AI interactions actually land with customers.

The one thing Alli looks for across every sales team she's worked with

Across LinkedIn, Elmo Software and HubSpot, I asked Alli what separates consistent high performers from everyone else.

It has nothing to do with AI.

Grit and growth mindset. Angela Duckworth's research names grit as a stronger predictor of success than IQ, and Alli agrees.

The sellers who thrive in fast-changing markets aren't necessarily the ones with the best tech stack. They're the ones still willing to learn after 25 years in the game.

That trait is also what makes someone good at AI adoption. Curious, willing to experiment and not waiting until they feel ready. And right now, in a market moving this fast, it's arguably more important than any technical skill.

Listen to the full episode to find out:

• The tool Alli uses to train her own prompting skills, and how she uses it to build capability rather than just get answers.

• More on how HubSpot measures the ROI of AI enablement, the specific metrics they track, and what they do when the numbers reveal a gap.

• Why Alli brings pre-sales, sales and marketing into the same room for AI enablement, and the aha moments that only happen when they're all there together.

Alli and I also cover so much more from the balancing act between automation, authenticity and customer trust, the messy middle of CRM foundations, and why behavioural change still makes or breaks AI ROI.

Listen here.

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