At a time when AI is taking over the enterprise software sales function, is there a risk that it will take humanity out of sales? Or is it actually an opportunity to bring more humanity into sales?
It depends. Sales leaders who lead with empathy and apply AI in the right ways have a chance to build teams that listen more carefully, personalize with intent and help customers make sense of an overloaded world. Sales leaders who want AI everything or keep a command-and-control management style? Good luck with that.
On this episode of Work Tech Weekly, Ryan Estis, former Fortune 500 chief revenue officer, bestselling author, and corporate keynote speaker, joins us to talk about what it actually takes to lead teams through this moment.
The thesis is simple: AI only delivers if you use it to make your people more human with customers, not less. As Ryan puts it, “It’s not about the software. It’s about leveraging the software to become increasingly more human. That's what our customers want.”
In this conversation, we dig into human-centered leadership, what needs to be unlearned, and what separates events that change behavior from the ones that just burn budget.
As Ryan points at, the average sales professional spends less than 30% their week actually selling, according to Salesforce research. The rest is a combination of emails, meetings, CRM updates, and what he calls “administrivia.” AI can do many of these tasks quickly and efficiently. When you take away half of someone’s workload, they suddenly have time to do the thing that actually moves deals forward: real conversations with real people.
The data backs this up, too. Teams using AI in their daily work are twice as likely to hit their performance targets. But most organizations are botching the execution. It’s more important than ever to strike the right balance of tech and humanity, then use the time savings wisely. “Capture that time and opportunity to spend it with clients or prospects doing the things that a skilled sales person in the field should be doing,” Ryan says. “I believe deeply that for quality enterprise B2B sellers, this is their defining moment.”
Why? Customers want sales experience to add value at every step and salespeople to have a sense of urgency. What they need is a human who understands their world and can help them see their own future differently. AI can create the space for sales to do that work, but it can’t do that part of the job for them. “Our customers are overwhelmed. They're inundated with information,” he says. “They need experts and sense makers and guides for making the right decision.”
If AI handles the transactional work, what's left for humans? Everything that it can’t do, like empathy, coaching, and building emotional intelligence.
Ryan rejects the term “soft skills” outright, and he's right to do so. “Empathy, particularly for the sales and the revenue function, is one of the most critical leadership and producer competencies,” he says. “It’s one of the hardest things to do.” The ability to actually listen, read the room and pick up on what's not being said is the competitive edge. “EQ trumps IQ. We've got machines that can think a lot faster than we can now, and that's only going to increase. So, what's left is human-centricity, and that's what we believe is true.
Ryan tells a story about his best boss, a man named John. They haven't worked together in 16 years, but if Ryan sent him a text right now, John would be on the phone in 5 minutes. That’s the kind of relationship that transcends employment. “At the end of Q3, when he called and said, ‘Hey, we're gonna fall short, what do you have?’ I wanted that call,” Ryan says. “Delivering results was good for me, but I wanted to do it for him because of what he had done for me.”
That's what human-centered leadership looks like in practice. People perform better when they feel supported, when they're coached with precision, and when they believe their leader actually cares. “Leadership isn’t a job, it's a responsibility,” Ryan says. “And it isn’t about us. It's about helping other people become the best they're capable of being.”
Ryan has led hundreds of sales kickoffs and is an expert in maximizing their impact. He’s seen what works and what's a waste of money. His diagnosis is sharp: Most kickoffs and strategic initiatives fail because they’re designed to create a feeling instead of a behavior change.
“The most important minute of a kickoff meeting is 8:01 a.m. on Monday morning, when you get back into the business,” he says. “What are you going to go do and do differently based on the investment that was made? If there's no throughput, no follow-up, and no accountability, it was just an expensive party.”
Ryan breaks down what actually makes a sales kickoff work: alignment around strategic priorities, skill development tailored to the moment, and connection across teams. But all of that collapses if leadership doesn’t follow through. “If you don’t have managers in the field driving these initiatives forward, they fall apart,” he says.
The lesson applies beyond sales kickoffs. Any major initiative — a company-wide training, a new tool rollout, or a strategy shift — lives or dies on the same principle. Clear expectations. The tools and training to meet them. Ruthless follow-through with the same rigor you’d apply to a quarterly review.
The takeaway: Strategic initiatives are measured by what happens afterward and whether your leaders are actually living it.
The future belongs to leaders who understand that AI is a tool to reclaim time, not replace judgment. And it belongs to teams who treat empathy, coaching, and sense-making as the hard skills they've always been.
If you're leading teams into 2026, the question isn’t whether you'll adopt AI. It’s whether you’ll stop tinkering with it and start using it to become more human.