Mastering Modern Selling in the Age of AI: How to Prospect Smarter, Close Faster, and Stay Human

This has been called the best show people have attended on AI in sales.

Tom Burton and I shared thoughts on one of the most critical shifts in our profession: how AI is rewriting the rules of modern selling, in the latest episode of Mastering Modern Selling.

And guess what? It’s not some far-off future.

It’s here.

It’s now.

And it’s not just about automating tasks. It’s about amplifying YOU—your message, your reach, your effectiveness, and your ability to connect deeply with the right people at the right time.

Let’s talk about how to master modern selling in an AI world—while staying radically human.

Where Are You Getting Stuck?

Every seller has a sticking point. Maybe it’s prospecting. Maybe it’s follow-up. Maybe your forecasts are based on wishful thinking instead of actual science.

For me, AI has become my go-to partner in dissecting every stage of the sales cycle and finding new ways to improve probability of success. Because at the end of the day, that’s what sales is—a game of odds.

Here’s how I break it down:

Planning and Territory Design Whether it’s the start or end of your fiscal year, AI helps you analyze your book of business. What’s your addressable market? Where are the gaps? What patterns does your data reveal? What should you focus on next? I’ve literally prompted AI to review my Power BI dashboards and generate a strategic plan for each workload.Prospecting Let’s be clear—I love prospecting. I’m one of those sickos. But now, with AI, I can write tailored outreach to 600 leads in minutes. I can scan LinkedIn profiles, customer websites, and news alerts to craft 3-bullet-point value messages that speak directly to someone’s mission—and AI helps me do it 10X faster and smarter.Customer Ghosting and Objection Handling Ever get ghosted after a great demo? Me too. Now I ask AI: “Write me a short message in my tone that derisks their fears and reopens the door.” It gives me empathetic, insight-driven language that gets responses and restarts the conversation.In-Meeting Reinforcement In real-time, I use AI to generate talking points while I’m in the room with a CEO. My brain might come up with 3–5 value props. AI gives me 6–10. And sometimes, bullet #7 is the one that gets the head nod.Forecasting and Goal-Setting No more guessing. I plug in last year’s data, historical benchmarks, and customer insights. AI helps me extrapolate targets that are both bold and realistic. I can even factor in variables like funding shifts or executive turnover. The AI Tools I Use Daily

Here’s my real-world toolkit:

Microsoft Copilot: Internal data like CRM, transcripts, Outlook, and LinkedIn—all in one view.ChatGPT 4.0: External-facing messaging, company research, executive prep, value messaging.Power BI + Excel: Pump dashboards into AI to uncover gaps and produce strategic plans.Sales Navigator: Combine with AI to identify the right contacts and trigger moments (e.g., a new CMO).

AI is my 24/7 sales coach, marketer, and analyst. But here’s the catch…

You Are Still the Final Editor

AI can draft the message, but it can’t deliver it with your heart. AI can highlight insights, but it can’t form relationships. AI can help you scale, but it can’t replace trust.

Every message, every call, every touchpoint still needs your humanity—your voice, your authenticity, your understanding of the person on the other end.

Because you don’t sell to accounts.

You sell to people.

The Opposite Strategy: How I Broke Through 100+ “Uncrackable” Accounts

Last year, I asked my team to give me their toughest accounts. 150 of them.

Using AI, I crafted brief, bullet-point-heavy, custom outreach to 50+ contacts per account.

I didn’t need 50 responses. I needed one.

We opened over 100 accounts. Deals that had gone untouched for years. Why?

Because AI helped me be fast, focused, and bold. But it was me—a real human—who built the trust once the conversation started.

How to Get Started with AI in Sales (Right Now)

If you’re new to AI or haven’t embedded it into your sales process yet, here’s my advice:

Start with Frustration What slows you down? Ghosting? Cold outreach? Follow-up? Let that be your entry point.Use AI to Research Prep for meetings like never before. I ask AI: “I have a meeting with the CFO of XYZ. What should I know?” Then I walk in like I’ve read every report they’ve ever published.Prompt Smarter Instead of asking for “an email,” try: “Write me a 3-sentence message to the CEO of a nonprofit healthcare org based on this URL and LinkedIn profile, aligned to their mission, in my tone.”Speed Wins Deals Whether it’s writing follow-ups, building newsletters, or generating slides—AI saves time and amplifies your brainpower. Use that time to focus on relationships. The Future Belongs to Sellers Who Blend Tech and Touch

What’s coming next?

Hyper-personalized signals. Deeper forecasting. Autonomous AI agents handling early pipeline stages. But here’s the truth:

The sellers who survive are the ones who evolve. Not just with tools—but with mindset.

You’ve got to constantly reinvent.

You’ve got to lead with empathy.

You’ve got to stay human while everyone else goes robotic.

That’s the only way to win—and win big—in the new era of modern selling.

Let’s build this together. Let’s rewrite the playbook. Let’s master modern selling—with AI by our side, and heart in every handshake.

For my entire $1B Moneyball sales playbook including AI and LinkedIn for Sales, check out “The Show Must Go On”

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