Enterprise selling is evolving fast, and the salespeople who understand what is coming are going to pull away from the rest of the field. In this episode of Ask Jeb on the Sales Gravy Podcast, Brian, a sales leader in Canada managing an enterprise team selling into large organizations, brings a big question: where is AI taking enterprise sales over the next few years, and what does that mean for sellers and their teams today?

Jeb's answer might surprise you. He believes AI is about to flip the information advantage back to salespeople. For years, it has been said that buyers need salespeople less and less due to the wealth of information widely available. Jeb breaks down why that is about to change, and why the sellers who learn to use AI as a research and intelligence engine will walk into accounts as true consultants with information their customers do not have.

But there is a caveat. Lazy salespeople and low-skill salespeople will not be able to operate in that environment. The technology only amplifies what you bring to the table.

Brian and Jeb also dig into a challenge a lot of enterprise teams are facing right now: getting back in front of customers after years of leaning on virtual meetings. Jeb makes a point that challenges every salesperson who has ever said their customers do not want to meet in person. Spoiler: it is not your customers who are avoiding the meeting.

In this episode you will learn:

• Why AI is poised to flip the information advantage from buyers back to sellers
• What the human-to-human relationship looks like in long, complex sales cycles
• Why salespeople project their own avoidance onto their customers and how to stop
• How to ask for a meeting with confidence instead of leaving the decision to your prospect
• The egg timer story: how Jeb turned a five-minute ask into an hour-long executive conversation
• Why great discovery and genuine curiosity will always outperform a polished pitch

Whether you are leading an enterprise team or carrying a bag yourself, this episode is a direct challenge to the habits that are keeping you from getting in front of the people who can actually buy.

Got a question you want Jeb to answer? Submit it at salesgravy.com/ask and you could be featured on the next Ask Jeb.

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In this episode of Money Monday, Keith Lubner fills in for Jeb Blount and breaks down the one metric that actually predicts sales success: the First Time Appointment (FTA). Using the Moneyball story as a framework, Keith explains why FTAs are the sales equivalent of getting on base — and how tracking them can transform your pipeline, your coaching conversations, and your close rates.

🎟️ Grab your tickets for OutBound Conference

📖 Purchase Jeb Blount's new book, 90 Days to Level Up Your Sales Skills

📝 Download the FREE 25 Ways to Ask for an Appointment on a Cold Call

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Buyer resistance is higher than ever, and most salespeople are losing deals because they lack the emotional intelligence to push through it. In this episode of the Sales Gravy podcast, Jeb Blount Jr. sits down with Colleen Stanley, Founder of SalesLeadership and author of Emotional Intelligence for Sales Success, ahead of her keynote at Outbound 2026.

Colleen breaks down why delayed gratification, internal locus of control, and assertiveness are the real drivers behind consistent pipeline movement. She also challenges sales leaders to rethink their hiring practices in an AI-driven world — because learning agility and teamwork are now non-negotiable.

🎟️ Grab your tickets for OutBound Conference

📖 Purchase Jeb Blount's new book, 90 Days to Level Up Your Sales Skills

📝 Download the FREE 25 Ways to Ask for an Appointment on a Cold Call

🔗 Follow us on LinkedIn!