How AI-Powered Clienteling Helps Retailers Turn Holiday Shoppers Into Loyal Customers

1. What are retailers getting wrong about turning holiday shoppers into long-term customers, and how can personalized follow-up help extend the relationship beyond the first purchase?

Retailers put a lot of focus on the holiday shopping rush, but they can miss the opportunity to build a relationship with customers who may be shopping with them for the first time. During the holidays, associates learn what customers are looking for, what they like and what matters to them. That gives retailers a starting point for future conversations, but those details often go unused once the holiday rush is over.

A personalized follow-up gives customers a reason to think about the brand again, whether an associate checks in about a purchase or reaches out with a product that fits their interests. Endear’s research found that 63% of shoppers are more likely to return to a store when an associate follows up with them personally, and more than half have made an additional purchase as a result. A customer who came in for a holiday gift might not have planned to shop with that brand again, but a thoughtful message can give them a reason to return.

2. How can retailers use customer data and AI to help associates deliver more personalized outreach at scale without making those interactions feel automated?

Retailers have a lot of information about their customers, but associates don’t always have the time to sort through it and decide who to contact. When an associate is helping customers on the floor and managing hundreds of relationships, it can be difficult to remember each person’s interests and find the right reason to reach out.

AI can help associates prioritize customers and suggest messages based on their purchase history and previous interactions. Associates can then review and personalize those suggestions before sending them, using what they know about each customer to make the outreach feel relevant. We found that retailers using AI for clienteling increased associate-led outreach sixfold in six weeks without adding headcount. This shows how AI can help associates reach more customers while keeping the personal touch that makes clienteling effective.

3. What role should AI play in clienteling, and how can retailers make sure associates remain at the center of the customer relationship?

AI can help an associate understand what a customer has purchased and suggest what might be relevant to them next. But purchase history doesn’t tell the whole story. An associate might know that a customer was shopping for a special occasion, was deciding between two items or had a specific concern that never showed up in their purchase history. That context can make the difference between a message that feels personal and one that feels like any other marketing email.

Retailers should use AI to support an associate’s judgment, not replace it. Associates can decide whether a suggestion makes sense, how to approach the customer and what they want to say. The goal is for customers to feel that the brand remembers them and understands their preferences, even when they aren’t in the store. AI can make that kind of personal attention possible across more customer relationships.

4. How do you see AI changing the role of the store associate as retailers look for new ways to build repeat customer relationships?

AI gives store associates more ways to stay connected with customers after they leave the store. Our analysis of more than 100 million SMS messages and 2.2 million clienteling interactions during Black Friday week 2025 found that customers who received tailored outreach from store associates were 30 times more likely to purchase than those who received traditional marketing emails or SMS blasts. Clienteling-driven revenue also grew 22% year over year.

These results show that the relationship between an associate and a customer can continue to influence shopping decisions long after a store visit. AI can make it easier for associates to keep in touch with more customers, share relevant recommendations and give people a reason to return. That expands the associate’s role beyond helping with the immediate purchase to building relationships that bring customers back over time.