Retail is a game of attention. Winning it once is hard enough. Keeping it is even harder. Stores spend billions chasing new customers, yet the real money isn’t in the first sale, it’s in the second, the third, and every one after that. The brands that figure this out don’t just sell. They build relationships.
Few know this better than Leigh Sevin, co-founder of Endear, a retail CRM company helping brands like Reformation, Glossier, and UNTUCKit turn casual buyers into long-term customers. “To us, it’s shocking that so much software investment has been focused on e-commerce while retail associates, who drive the bulk of revenue, are left under-supported,” Sevin says.
Endear isn’t another mass marketing tool and it’s not designed to blast the same discount code to every inbox. Instead, it arms store associates with one-to-one messaging, helping them reach customers through email, SMS, and WhatsApp, just like a trusted stylist or a personal shopper might. Since its inception, brands using Endear have seen a 19% increase in online spending per order.
The Shift to Clienteling
The retail playbook is changing as shoppers get tired of faceless transactions. They want a human touch, even when they aren’t inside a store. Companies have tried loyalty points, automated emails, and AI chatbots. But few strategies work as well as clienteling, the old-school art of remembering what someone likes and making sure they feel valued.
“Customers don’t see ‘online’ and ‘offline’ as separate, they just see the brand,” Sevin explains. “That’s why bridging the gap with personal outreach is so powerful.”
At its core, Endear gives sales associates the same data and tools that e-commerce teams have had for years. If a customer browses a dress online but doesn’t buy, a store associate can see that. They can follow up, send a message, maybe suggest a jacket that pairs well with it.
Where The Money Is
85% of all retail sales still happen in stores, yet most marketing budgets chase online growth. Retailers have spent years fine-tuning Facebook ads and SEO, only to discover that acquisition costs keep rising and that the real value is in the customers they already have.
Sevin puts it bluntly: “The real gain from AI in retail isn’t chatbots, it’s making sales teams more efficient and effective at selling.”
That efficiency is what sets Endear apart. Instead of relying on discount-driven marketing, it helps brands create direct relationships. Instead of treating customers as numbers in an algorithm, they’re treated like individuals with purchase histories, preferences, and habits that smart retailers can learn from.
Reformation, Glossier, and The Power of Personal Touch
Reformation uses Endear to send personalized follow-ups after in-store visits. If a customer tries on a dress but leaves without buying, an associate can send them a quick message. Sometimes, that’s all it takes to turn hesitation into a sale.
Glossier, known for its loyal customer base, takes a similar approach. The beauty brand fosters community engagement by keeping store associates in touch with top customers, recommending products, and offering early access to new releases. It’s clienteling at scale.
“Retailers who prioritize personal relationships over transactions will be the ones that win in the long run,” Sevin says.
What’s Next?
Endear recently closed a $6M Series A led by Channel Equity Partners, a firm that backs companies focused on sustainable growth. Unlike many tech startups, Endear isn’t chasing aggressive expansion at all costs. Instead, the company plans to refine its AI tools, expand into new markets, and continue giving retailers a better way to keep customers engaged.
“AI helps retailers work smarter, but real customer loyalty is built through human connection,” Sevin explains. Endear’s AI identifies high-intent shoppers, suggests the best outreach strategy, and even offers personalized messaging prompts.
As automation and AI continue to reshape the industry, the brands that win will be those that use technology to deepen relationships, not replace them. Endear’s approach reflects this balance, blending data-driven insights with human connection to create a smarter, more personal way to sell. As retailers navigate an increasingly competitive landscape, the question isn’t whether they should invest in retention, it’s whether they can afford not to.
