Hello go-to-market (GTM) leaders, strategists, and innovators! 👋 Thank you for dropping by to learn practical AI applications and gain strategic insights to help you grow your business and elevate your team’s strategic value.
Quick Take
Will Guidara took Eleven Madison Park from a struggling two-star brasserie to the number one restaurant in the world. His secret wasn’t better food. Every restaurant on that list had exceptional food. His breakthrough came from making hospitality systematic across every customer touchpoint. He wrote about it in his New York Times bestselling-book Unreasonable Hospitality.
What Guidara did manually at one restaurant, AI can help us do at scale across thousands of customers. But most companies are using AI for automation to reduce human interaction. But what about using AI to enable more meaningful human connection throughout the entire customer journey?
Top takeaways in this newsletter:
- AI features become table stakes quickly. Relationships built over time are the defensible moat.
- While we can delight customers with surprise moments, the goal is to consistently make them feel understood using info they willingly share.
- The Unexpected Experience Maturity Model shows the progression from Random Acts to Trust Moat, with most companies at Stage 1 or early Stage 2.
- Systematic relationship building requires breaking down silos. Product, marketing, sales, and customer success must work as one connected experience.
- AI should free us to be more human, not less. When AI handles analysis and pattern recognition, we can focus on connection.
In this newsletter, I’ll show you exactly what this looks like for B2B customer touchpoints, from webinars and content engagement to discovery calls and customer milestones. Plus, I’ve created a custom GPT that helps you design unexpected experiences tailored for your business and customers.
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The Moment It Clicked
There were many excellent sessions at Pavilion‘s GTM2025 event in DC, but Guidara’s keynote was different. He wasn’t talking about customer service or restaurant operations. He was talking about using systematic approaches to make people feel genuinely seen and valued.
As he walked through examples from Eleven Madison Park, I realized he was showing us what systematic relationship building looks like when done with intention and care.
Then I found Steven Bartlett‘s interview with Jimmy Fallon, host of The Tonight Show. Bartlett shared his preparation process: monitoring CO2 level during interviews, creating custom playlists from guests’ first concerts, and handing Jimmy a personalized book of quotes and photos from the interview as he left. Jimmy said he cried in his car.
The Defensibility Shift
But Guidara and Barlett showed me what this actually looks like in practice. While competitors build AI wrappers and chase feature parity, companies that stand out use AI to build systematic relationship excellence.
Will Guidara: Making Unreasonable Hospitality Systematic
Will Guidara took Eleven Madison Park from a struggling two-star brasserie to the number one restaurant in the world. His secret wasn’t better food. Every restaurant on that list had exceptional food.
His breakthrough came when he gathered his entire staff and asked them to list every customer touchpoint. After one hour, they had 30. After three hours, they had 120.
Then they worked through each touchpoint asking: how can we make this moment exceed expectations?
The hot dog story became legendary. Guidara overheard European guests mention their only regret was leaving New York without trying a classic street hot dog. He ran outside, bought hot dogs from a cart, brought them back to the kitchen, and had his Michelin-star chef plate them perfectly. The guests went wild.
But the hot dog story wasn’t what made Eleven Madison Park number one in the world. That was just one moment. What created their success was doing this consistently for years. One surprise creates a story people share. Systematic surprise creates trust that keeps them coming back.
Another family visiting from Spain mentioned their kids had never seen snow. Guidara’s team bought sleds, hired a limo, and took the family to Central Park for sledding before they returned to Europe.
These weren’t random acts of kindness. They were systematic. Guidara created a team called “Dreamweavers” whose job was to listen for these moments and act on them. He called it spending the “foolish 5%” of your budget on experiences that create lasting memories.
Captions are auto generatedPlayWill Guidara’s Keynote Session at Pavilion’s GTM2025 in DC
What if AI could identify those moments across hundreds of customer interactions? What if your team always knew exactly when and how to exceed expectations? The system becomes the moat.
Steven Bartlett: Sweating the Small Stuff at Scale
Steven Bartlett hosts The Diary Of A CEO, one of the world’s most popular podcasts with over one billion streams. His preparation process shows how systematic attention to detail builds unforgettable experiences.
Before each interview, Bartlett researches everything. When Jimmy Fallon appeared on his show, Bartlett knew about his first concert with “Weird Al” Yankovic. He created a custom playlist including that music for when Jimmy walked in.
But it goes deeper. Bartlett monitors CO2 levels during interviews because research shows that levels above 1,000 parts per million reduce cognitive capacity by 21%. For his first 200 episodes, he was essentially drunk because the room wasn’t properly ventilated.
He thinks about the scent in the room, the lighting, every detail. Then he applies the peak-end rule: people remember the peak of an experience and how it ends.
So when Jimmy finished his interview, Bartlett’s team handed him a personalized book. It contained photos from their conversation and actual quotes Jimmy had said during the interview, created in real time while they talked.
Jimmy shared on his show: “I got in my car when I left and I started crying. It’s the greatest thing ever.”
That’s the power of systematic relationship building. Bartlett used research tools, data monitoring, and systematic processes. But none of that tech is what Jimmy remembers. Jimmy remembers how he felt.
The more tech Bartlett used, the more human the experience became. That’s the irony most companies miss: they’re using AI to automate away human interaction, obsessing over efficiency – the means. But the defensible outcome is authentic human connection.
AI should free us to be more strategic and more genuinely human, not less.
Building Trust Without Being Creepy
Here’s the question you might be asking: does this approach require monitoring customers without their knowledge? No, absolutely not.
Maya Angelou said it best, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
You don’t need secret data to make people feel understood. You need to care more about the information they willingly share than your competitors do.
For example, your competitor gets a question during the webinar and sends a generic follow-up email. You get the same question and send a personalized resource addressing their specific challenge, plus an intro to someone who solved it. It’s the same data, different level of care, completely different feeling.
Yes, you lose some element of surprise when customers opt in to share info. But you gain trust. And trust sustained over time is what makes relationships truly defensible.
Competitors can copy your surprise tactic tomorrow. They can study Guidara’s hot dog story and try their own version. They can’t copy years of consistent care that builds deep trust.
What This Means for B2B and GTM
Both examples show what was done through human attention and systematic processes that AI can now help us do at scale: identify touchpoints, understand context, predict needs, and enable humans to act on those insights.
Here’s an example how this translates to B2B when done systematically over time, using only information customers willingly share:
The Multiplier Effect
When customers say “they really get us,” they’re not talking about the technology. They’re talking about how the technology enabled humans to show up as trusted advisors instead of vendor reps.
Notice how managing these touchpoints requires breaking down silos. Product, marketing, sales, and customer success can’t operate separately when you’re systematically exceeding expectations at 50+ touchpoints per customer. AI becomes the connective tissue that lets everyone see the full picture.
I explored this dynamic using the chart below in AI is Breaking Department Silos: Moving from Org Charts to Work Charts.
The Pattern Behind These Stories
Both Guidara and Bartlett share the same approach to building defensible advantage. They built systems to identify moments that matter, then empowered humans to act on them. The relationship is the work.
This approach works regardless of company size. A 50-person startup can build this moat as effectively as a 5,000-person enterprise. The differentiator isn’t budget or headcount. It’s commitment to making customers feel valued over time.
David Samuels, CEO of AgentSync and former Chief Customer Officer at SAP and Chief Commercial Officer at Pie Insurance, shares his perspective from leading customer organizations at scale:
I’ve seen that customers don’t remember your automation – they remember the moments when someone actually understood their challenge.
The companies using AI to identify those moments at scale, then empowering humans to show up with real value, are seeing it in retention metrics. It’s the difference between a 70% renewal rate and 110% net retention.”
This is about values, not just choice. Do you value efficiency or relationships? AI can serve either. Most companies default to efficiency because it shows immediate ROI. The defensible companies choose relationships and commit to them over time.
The Unexpected Experience Maturity Model
Most companies approach customer experience in one of four ways:
Stage 1: Random Acts – Occasional surprises with no system. Customer delight is inconsistent.
Stage 2: Mapped Moments – You’ve identified your customer touchpoints and know where opportunities exist. But execution is still manual and varies by person.
Stage 3: Systematic Care – AI spots patterns and flags opportunities while humans deliver personalized attention at scale. You’re consistent across all touchpoints using information customers willingly share.
Stage 4: Trust Moat – Consistent care over time makes the relationship your defensible advantage. Competitors can’t replicate years of earned trust.
Most B2B companies are at Stage 1 or early Stage 2. The defensible companies are building toward Stage 4.
Understanding Your Starting Point
Most companies don’t sit at just one stage across all touchpoints. You might be at Stage 3 for webinar follow-up (AI finds patterns, team acts systematically) but Stage 1 for customer milestones (completely forgotten or inconsistent). Your marketing team might have mapped moments while sales still operates on random acts.
This is normal. The framework helps you see where each critical touchpoint is today and prioritize which ones to move first. Start with touchpoints that have the biggest relationship impact and work systematically through the rest.
Here’s how to move forward:
In my newsletter A Leader’s Playbook: How a Lean Team Transformed Into a Human-AI Powerhouse, I showed how one CMO built a 45-member team where 25 humans work alongside 20 AI teammates. Today, they have more than 100 AI teammates. That organizational structure is exactly what enables this systematic experience approach. The AI teammates handle research, analysis, and pattern recognition. The humans focus on relationships and exceeding expectations.
Custom GPT: Your Unexpected Experiences Ideator
I’ve created a custom GPT called Unexpected Experiences Ideator to help you get started. Answer a few questions about your business, customers, and touchpoints. Get personalized suggestions for how AI can help you exceed expectations at every interaction.
What’s Next
The companies figuring this out first will have customers who become true partners because the relationship grows stronger with every interaction.
Your competitors can copy your AI features. They can study your playbook. They can’t copy years of customers feeling genuinely understood at every touchpoint.
That’s the moat.
Try the Unexpected Experiences Ideator GPT to start building yours.
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For those who prefer more interactive learning, explore our applied AI workshops, designed to inspire teams with real-life use cases tailored to specific go-to-market functions.
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