During the INBOUND conference in San Francisco, Bart Kowalczyk, host of the H2H Sales Automation Podcast, sat down with Sarah McDevitt, Senior Director of Partners at HubSpot, to explore one deceptively simple question:
What if your best sales tool isn’t AI—but the person using it?
AI has transformed sales operations—automating research, drafting emails, and qualifying leads. Yet, Sarah argues that the most successful teams don’t compete against AI; they combine AI’s efficiency with human depth, empathy, and curiosity.
“It’s not humans versus AI - it’s humans versus humans,” Sarah emphasises.
Every rep now has access to similar automation tools. The differentiator is the quality of human interaction: who listens better, who reads the room, who shows up with curiosity and authenticity.
A good rep asks questions; a great rep hears what’s unsaid - tone, hesitation, subtext—and uses it to create value. That ability to interpret emotional signals is where deals are won.
Sarah introduces a concept she calls empathetic structuring—a deliberate way of building accountability and openness into the sales process.
Instead of the rep carrying the full burden of discovery, both sides share responsibility for reaching the best outcome.
“Make customers aware they’re accountable for sharing information,” she explains. “That’s how you reach the real answer together.”
In practice, empathetic structuring means explaining why questions matter, mirroring the buyer’s goals, and creating a tone of collaboration rather than interrogation.
Bart, CEO of AutomateNow, in San Francisco after interviewing Sarah McDevitt at the HubSpot Partners Lounge during INBOUND.
Why do so many reps rush calls or rely on canned talk tracks? Because they’re pressed for time.
Missed planning leads to end-of-month panic; panic crushes presence.
Sarah sees AI as a way to reclaim that space:
Automate scheduling, CRM updates, and summaries—then use the extra hours for genuine connection.
“If you’re not pipeline planning, you’re not giving yourself the space to connect,” she warns. “And connection is what creates future sales opportunity.”
Sarah breaks the modern sales workflow into three buckets:
20 % AI-Only: Tasks that require no human oversight—data entry, enrichment, meeting summaries.
20 % AI + Human: Collaboration between people and intelligent agents—drafting proposals, analysing calls, suggesting next actions.
60 % Human-Only: The core of selling—listening, discovery, negotiation, trust-building.
Reps who treat all three buckets as equal end up starving the last one. Protecting the human 60 % ensures time for curiosity, storytelling, and emotional calibration—the traits AI still can’t fake.
Conventional wisdom says trust takes years to build and seconds to lose. Sarah disagrees.
“If authenticity, logic, and empathy are present, you can build trust in a matter of moments.”
Being prepared with insights (logic), showing up as yourself (authenticity), and showing genuine concern (empathy) are the three fast-acting ingredients. The first impression becomes the trust foundation.
At INBOUND, many HubSpot partners shared an “aha” moment: the end of the delivery mindset.
“Delivery” implies a finish line. Modern revenue work is looped—test, learn, iterate, and repeat.
Loop Marketing reframes services from one-off projects into continuous improvement cycles.
For HubSpot partners, like AutomateNow, that means evolving from “technical implementers” to complexity experts—professionals who orchestrate cross-team collaboration and help clients keep learning from their own data.
AI will democratise many technical skills. Tomorrow, every agency and rep will have similar tools.
What will differentiate them is their comfort with complexity—human, geographic, organisational.
“Don’t sell yourself as technical,” Sarah advises partners. “Be a complexity expert. The tools will change. Complexity won’t.”
Sarah’s upcoming book explores relational intelligence through personal stories.
It’s a call to resist the “disconnection epidemic” of modern work—where speed and automation can crowd out empathy.
Interestingly, she co-wrote it with AI:
“Of course, I used AI—it would be silly not to. But the AI didn’t live my experiences. I did.”
The book models how humans can be amplified, not replaced, by technology.
If you remember one tactic, make it this:
Start every meeting with “How are you?”
Then follow up with, “How are you really?”
That second question breaks the automation loop. It signals presence, curiosity, and care—the foundation of long-term trust.
The next revolution in sales won’t come from faster algorithms but from slower, deeper human moments—where curiosity replaces scripts and empathy replaces noise.
AI handles the tasks. You handle the trust.
Because in the end, the most powerful sales tool is still you.
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