How Endear uses AI to help in-store sales teams send personalized messages

You won’t find “clienteling” in Merriam-Webster, and to the uninitiated it might seem like jargon for “customer service,” but don’t let anyone at Endear hear you say that.

Endear, a customer relationship management (CRM) platform that focuses on helping sales associates in physical stores with follow-up messaging, even goes to the trouble of disabusing those who conflate the terms in a blog post. Customer service is largely reactive, responding to issues customers have with returns or undelivered packages, the post explains. But clienteling is proactive and “uses data to anticipate needs, make personal recommendations, and create moments of delight before the customer even has to ask,” Endear wrote.

The point of clienteling is not to resolve complaints like the customer service department, the post continues, but rather to “foster a relationship that encourages repeat purchases and turns customers into brand evangelists.”

Now Endear is reporting that one of the key aspects of clienteling on its platform—sending personalized messages to customers rather than mass marketing email and text blasts—is gaining traction. Such personalized messages from sales associates in the 2,000-plus stores using the platform grew 50% YoY in the 12 months that ended April 30, per Endear.

So how did Endear help boost such messaging, and help drive more repeat purchases and bigger orders for its retail partners?

The answer combines the age-old imperative of retailers getting to know their customers better with emerging AI technology that enables them to do so en masse.

The message is the medium: Leigh Sevin, co-founder of Endear, told Retail Brew that while stores typically email or text customers to inform them about a sale or special offer, clienteling “almost flips that model on its head.” Rather than telling customers what the store’s doing, she said, the platform helps ask customers, “What are you doing?”

The platform helps store associates surface what customers discussed the last time they shopped in the store and helps craft missives that refer to those discussions.

Yes, Sevin acknowledged, sales associates taking notes on customers and schmoozing with them has been a cornerstone of commerce “since the dawn of retail,” but the platform simplifies and automates the process.

The platform uses artificial intelligence to help throughout the process. Its Notetaker tool allows store teams to add voice memos, video recordings, and even audio and video of the customers’ store visits if they’re game, and then distills all that information in the customer profile. When it comes time to connect again with customers post-sale (perhaps following the industry standard “2-2-2” rule of following up after a couple days, weeks, and months), the platform’s AI can draft personalized messages in what Endear calls the brand voice.

Thus, rather than paralyzing associates at message-sending time with the cold sweat-inducing blank page, it “dramatically increases the likelihood” that they send the message, “that that message converts, and the likelihood that customer comes back,” Sevin said.

The average open rate of marketing emails is 30.4%, per Omnisend. Endear reports that more than twice that, 66%, sent on its platform are opened.

Cosmetic differences: Jones Road Beauty, the brand founded by makeup artist Bobbi Brown, began piloting the Endear system in October 2025. The goal was for sales that resulted from the back-and-forth between associates and their customers over the platform to account for 10% of the revenue at all the stores, Amanda Aldecoa, regional director at Jones Road, told Retail Brew.

Some stores have already smashed that goal, including Jones Road’s Upper East Side location, where sales resulting in personalized messages now account for about 22% of its sales, Aldecoa said.

It turns out that customers receiving messages through Endear also end up spending more per transaction than those not in the system yet.

“What we have found using Endear is that the AOV”— that’s average order value in industry parlance—“is actually higher for clients that are client outreach and have a relationship versus customers who just purchased maybe one time,” Aldecoa said.

And it appears the clienteling cohort is adding more than just an $8 product-scooping spatula to their orders; their AOV is 41.3% higher than non-clienteling customers, per Jones Road.

What makes the customers so spendy is that they’re not getting a generic do-not-reply email about a sale but rather an email from, for example, Brianna at your local store asking how the Dusty Rose Miracle Balm blush worked during that weekend on Nantucket.

“We’re here for a resource that goes highly underutilized, which is the store associate,” Sevin said. “We want store associates to feel empowered to know who to reach out to and what to say all day, every day.”