AI features get commoditized fast. Everyone’s adding chatbots, automation, predictive analytics. Your competitors will copy those in weeks. The defensible moat is how systematically you build relationships that customers remember.
Will Guidara’s keynote at Pavilion’s GTM2025 event shifted how I think about AI and relationships in practice. Guidara took Eleven Madison Park to number one in the world by identifying 120 customer touchpoints and asking at each one: how can we exceed expectations?
The hot dog story and sledding trip for kids who’d never seen snow weren’t random acts. They were systematic.
Steven Bartlett does the same with his billion-stream podcast – monitoring CO2 during interviews, creating custom playlists from guests’ first concerts, building personalized books in real-time. Jimmy Fallon cried in his car after receiving his.
This translates directly to B2B. I’ve created The Unexpected Experience Maturity Model showing four stages companies progress through:
Stage 1: Random Acts → Stage 2: Mapped Moments → Stage 3: Systematic Care → Stage 4: Trust Moat
Most B2B companies operate at Stage 1 or early Stage 2. The defensible ones are building toward Stage 4.
Key takeaways:
AI features become table stakes quickly. Relationships built over time are the defensible moat.
While we can delight with surprise moments, the goal is consistently making customers feel understood using info they willingly share.
The Unexpected Experience Maturity Model shows progression from Random Acts to Trust Moat.
Breaking down GTM silos becomes necessary when systematically exceeding expectations across many touchpoints.
Custom GPT included to help design unexpected experiences for your business
Featuring insights from Will Guidara, Steven Bartlett, and David Samuels (former CCO at SAP, now CEO of AgentSync) on what separates 70% retention from 110% net retention.
See the full framework, B2B touchpoint examples, and access the custom GPT in the newsletter below.
A 15-min AI podcast version of the newsletter is also available (link in comments) to cater to different learning styles.
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