Gladly chief revenue officer Andy D’Amato discusses why the same AI experience is costing companies their highest value customers now—and their most valuable ones next.
Your highest value customers are the least forgiving of your AI. And the customers who will define your revenue five years from now are already judging it by standards most companies haven’t started tracking.
Most companies don’t realize either of these things because the metrics they use don’t show it.
Boomers and Gen X together account for roughly 66% of U.S. consumer spending, according to Circana. Boomers alone represented 33.7% of total holiday spend in 2025, per PwC. These are your biggest spenders right now, and their tolerance for AI-mediated service is low. Just 11% of Boomers and 36% of Gen X are willing to go more than five exchanges with an AI before they expect to talk to a person, according to the 2026 Customer Expectations Report, a survey of 1,000 U.S. adults who actively use AI-powered customer support.
On the other end, Gen Zers accounted for 5.6% of holiday spend in 2025, but their share has more than doubled since 2020. They’re entering peak earning years. Their purchasing power is compounding. And they’re already the most demanding generation when it comes to what AI should be able to do.
Gen Zers tolerate more AI (56% will go past five exchanges), but they expect continuity across conversations, recognition of who they are, and context that carries forward from one interaction to the next. When that works, the loyalty payoff is real. When it doesn’t—when the handoff feels generic or the AI treats them like a stranger—26% say they’d walk away from the brand entirely.
Companies that read Gen Z as “the easy AI audience” are misreading the data. This is the cohort that will punish lazy personalization hardest as their wallets grow.
Two revenue problems hiding behind one dashboard
Most companies have built a single AI experience for their entire customer bases. The 58-year-old with a $12,000 annual spend hits the same automated loop as a 24-year-old browsing for the first time. These companies measure whether the conversations are closed. They don’t measure what those experiences cost in either direction.
In the near term, the cost is direct. Among customers who couldn’t reach a human when they needed one, 40% abandoned or switched brands. Of those who experienced a blocked escalation path, 47% said they’d avoid future purchases if it happened again.
But there’s a parallel cost that takes longer to show up in a quarterly report. Gen Zers are forming brand opinions right now, in their twenties, during the window in which loyalty habits take shape. If the AI experience they get today is shallow—no memory, no personalization, no sense that the company actually knows them—those impressions harden. By the time their spending power peaks, the relationship is already set.
The generational data makes the dual problem visible. The strategic question is whether companies can solve both at once.
Same infrastructure, different routing
Companies making progress here aren’t choosing between protecting current revenue and building future loyalty. They’re doing both on the same infrastructure with different routing logic.
For high-value customers with lower AI tolerance, that means shorter automated flows, earlier escalation triggers, and handoffs that carry full conversation history so customers never repeat themselves. This protects the revenue already at stake.
For customers more open to AI-driven interactions, it means longer self-service paths with real depth: recognition of past purchases, proactive recommendations, continuity across channels. Get this right for a 26-year-old today, and you’ve shaped a relationship that compounds over the next two decades of their spending.
The platform doesn’t change—the routing does. One path defends margin in the highest spend segment. The other builds lifetime value in the fastest growing one. A single undifferentiated AI experience does neither well.
The measurement gap is the real blocker
Forrester’s Customer Experience (CX) Index hit a new low in 2025—four consecutive years of decline—while companies are spending more on customer-facing AI than ever. If investment keeps rising while outcomes keep falling, the technology isn’t the issue. What the technology is being asked to optimize for is the issue.
Most companies will spend the next year refining a single AI experience for their entire bases and calling it progress because conversation volume went up and cost per contact went down. Those metrics matter. They’re also incomplete.
The companies that pull ahead will be the ones measuring two things simultaneously: whether their AI is protecting the relationships that fund the business today and whether it’s earning the loyalty of the customers who will fund it five years from now. The generational data to act on both already exists in their systems. The question is whether anyone’s looking at it.
The companies that keep treating AI as one dial to turn—optimizing for a single average customer who doesn’t actually exist—will keep watching CX scores decline while AI budgets climb. They’ll have optimized for neither the customers paying the bills today nor the ones who’ll decide whether the brand matters tomorrow.
See how Gladly helps companies build AI that works for every customer at gladly.ai.