How to Build a Clienteling Program Your Associates Will Actually Use

Why Good Clienteling Programs Stall

Ask any retail leader whether clienteling works and you'll get a quick yes. Send a thoughtful message to a customer who just bought something, and they're more likely to come back and spend again. Nobody needs a webinar to be convinced of that.

And yet plenty of clienteling programs launch with a big kickoff, a shiny new app, and a whole lot of optimism. Six months later, a few associates are still texting their regulars while everyone else has quietly gone back to waiting for foot traffic.

So what's going wrong?

We recently teamed up with KWI and ALC for a webinar on what the best clienteling programs look like behind the curtain. The panel brought three perspectives, including Casey Drake from Endear, Scott Matza from KWI, and Jennifer Varner, Director of Retail Operations at ALC.

We kicked things off by polling attendees on their biggest clienteling challenge. The top answer was, no surprise to anyone, store associate adoption.

Clienteling asks associates to do more than clock in, help whoever walks through the door, and clock out. Here are seven lessons from the conversation on making that extra work feel worth it (and a lot easier).

Lesson #1: Build Your Program for the Middle of Your Team

Every store has a few associates who were clienteling long before anyone gave it a name. These associates know your customers' names, their kids' names, and exactly which new arrival they'll love.

Here's the thing about your top performers. They would clientele well even if you told them nothing, because they already know it leads to more sales and more commission.

That means a clienteling program has a different job. As Casey put it, the goal is to bring your bottom and middle-tier associates closer to your best ones. When you design training, tools, and expectations, design them for the associate who wants to do well but doesn't know where to start. Your superstars will be fine either way, and as you'll see in Lesson #7, they can become your best teachers.

Lesson #2: Tell Associates Who and When, and They'll Figure Out What and Why

Telling a store team to "go build your client book" is a bit like telling a new hire to "go sell stuff." Technically correct, but not much help.

Casey breaks every good clienteling message down into who, when, what, and why.

• Who and when is the signal. Which customer should I reach out to, and why is today the right day? Maybe they just made a purchase, abandoned an online cart, or were waiting on a size that finally came in.
• What is the context that makes the message personal. What did they buy? What's in their profile notes? What did you talk about last time?
• Why is the incentive to engage, like a personal styling appointment, a VIP event, or a fit check on their recent purchase.

The part associates struggle with most is the who and when. Most associates are already great at the what and why, since connecting with a customer and giving them a reason to come in is the core of their job on the floor. So if your program can hand them the right customer at the right moment, you've solved the hardest piece.

Put all four together and you get something like this:

"Thanks for shopping with me last week! Hope you're loving that dress you picked out. Did you get a chance to wear it yet? How's it fitting? Just so you know, our return window is 30 days, so if it's not perfect, come back in and we'll find you something you really love."

That last bit about the return window is a nice example of what clienteling is really about. Casey recommends it because the goal is never one purchase. The goal is getting that customer to shop again and again, and nobody comes back to a store where they feel stuck with something they don't love.

Lesson #3: Connect Your Data So the Signals Come to You

You don't need any software to start clienteling. A great associate who genuinely cares can already reach out to:

• Customers the team already knows well
• Customers who recently made a purchase
• Customers with an open thread, like a special order or an alteration

Where a platform earns its keep is in spotting the signals people can't see on their own. Casey pointed to a few:

• Lapsed customers. In Endear, a customer starts to look lapsed when the gap since their last purchase stretches past their usual order frequency. If someone typically buys every 30 days and it's been 45, that's your cue.
• Quiet VIPs. When brands first load their data into Endear, the VIP list often looks different from who the store team expects. The VIPs associates name tend to be the chatty regulars who say hi to everyone. Meanwhile, some of your biggest spenders come in, buy, and leave without much small talk, and they could be treated a whole lot better.
• Moments. Birthdays, milestones, and wishlist items all make great reasons to reach out.

None of those signals work if the data behind them lives in five different places. Scott made the case that stores are starting at a disadvantage compared to ecommerce, since an associate often knows nothing about the shopper standing in front of them. =

The goal is a single view of each customer that pulls together:

1. In-store and online purchase history
2. Returns, and why something didn't work
3. Preferences like sizes, fits, and styles
4. Upcoming dates such as birthdays and anniversaries
5. Abandoned carts and saved-for-later items
6. Order status and product availability across the business

And associates need a place to write down what they learn in conversation, so that knowledge doesn't walk out the door when the shift ends. As Scott put it, if the data is spread out all over the place, associates just won't use it.

Lesson #4: Give Your Follow-Up Cadence Somewhere to Go

A thank-you text is a fine start. But sending a thank-you text followed by silence is how customers forget your associate's name by February.

At ALC, every follow-up builds on the last one. Here's the rhythm Jennifer described.

Within 24 to 48 hours: Thank the client and reference what she bought. If she was shopping for an event, ask her to send photos. Jennifer's teams genuinely love seeing a great look come together, and customers can tell.

After 7 to 10 days: Check in on how the event went and how the pieces are working out.

Around 30 days: Share what's new. This is where ALC's teams build look books from their own store's assortment, pairing new arrivals with pieces the client already owns.

That last step is where good data pays off. When you know what's already in a client's closet, a new arrivals message reads a lot more like advice from a friend with great taste.

Lesson #5: Write Like a Human, and Always Ask a Question

Our moderator raised a fair point during the Q&A. We've all bought something, then spent the next three weeks getting buried in follow-up messages. So how do you stay helpful without becoming one more notification your customer swipes away?

Casey's answer was refreshingly simple. Put a question in your message.

A question invites a reply, and a reply changes everything. Once a customer writes back and gets a real response, they realize there's an actual person on the other end. From then on, your messages live in a different mental folder than the promotional blasts filling up their inbox.

A few other ways to keep outreach feeling personal:

• Talk like you're on the floor. New clienteling users often start sounding like the marketing team the moment they switch to text or email. Your marketing team already sends those emails. Customers who shop in store do it because they like talking with you, so write the way you'd talk if they were standing in front of you.
• Keep brand voice guardrails light. Managers should be able to review messages and make sure nobody strays too far off-brand, but templates work best as a starting point that associates make their own.
• Let the system protect customers from overload. Endear, for example, blocks associates from accidentally sending more than one new message to the same customer within a 24-hour period, while still allowing replies within an ongoing conversation.

Lesson #6: Build Clienteling Into the Shift

Anyone who has worked retail knows associates juggle about a thousand things a day. If clienteling only happens "when there's time," it won't happen.

Casey was blunt about where the responsibility sits. Operations leaders and retail directors need to carve out a specific time in the day for this work. Some brands block off the first 15 minutes after an associate's break to sit in the back room and work through their clienteling opportunities. And yes, he acknowledged that some stores may need to schedule an extra person to free up that time. (He knew that one wouldn't be popular.)

At ALC, the routine happens first thing. Jennifer described a typical Wednesday where associates log in before the store fills up and work through who purchased recently, who has an appointment coming, and what each outreach should say. Task reminders pop up automatically, whether it's a client to contact when the fall collection launches or a nudge about a birthday discount waiting to be used. Most ALC stores run with two or three people on the floor, so one person can step away for 30 minutes to handle outreach.

When an attendee asked about the labor cost of all this, Jennifer's answer surprised a few people. When all the data lives in one place, ALC hasn't needed to spend extra labor hours on clienteling at all.

This is also the thinking behind Endear's AI Opportunity Engine, which ALC leans on daily for thank-you follow-ups, birthday outreach, and abandoned cart messages. Most apps want you spending more time in them. The Opportunity Engine is designed to get associates in and out fast, serving up the day's signals as a stack of cards they can accept, edit, or skip.

Lesson #7: Plan for Adoption Before You Launch

The first few weeks of a clienteling rollout matter more than any others. Casey described it as a snowball rolling downhill. When associates have early wins, they fall in love with clienteling, and it spreads from there. When they don't, the program stalls. Here's what the panel recommended to get that snowball moving.

Pilot first. ALC started with a single test store, gathered feedback for about two weeks, and then rolled out to everyone. Because the pilot surfaced the questions store teams were likely to ask, the full rollout took roughly a month.

Turn your superstars into teachers. Remember those top performers from Lesson #1? At ALC, they write the thank-you, birthday, and new arrivals templates the whole company can pull from and personalize. Many have also become trainers who help onboard new hires.

Make wins public. At a minimum, recognize the associates putting in the extra effort, and ideally back that up with commission or bonuses. ALC shares clienteling reports with the entire retail chain each week, and Jennifer has watched people push hard to land in the top five.

Get conversations off personal phones. Your best clientelers often have years of client relationships stored in their iMessages, and they can be the hardest to move. Casey suggests a simple pitch. If your outreach lives on your personal phone, I can't give you credit for it or brag about you to leadership. ALC also printed the Endear number on their new business cards, so clients reach associates in the app from day one. As a bonus, managers can see every conversation, so a client never gets dropped when an associate goes on vacation or moves on.

Make attribution easy to explain. Endear lets each brand set its own attribution rules, generally based on how recently a customer interacted with a clienteling message and how engaged they were (opening it, replying, or clicking a product or look book). Online purchases can count too, which helps end the old store-versus-ecommerce tug-of-war. Whatever rules you choose, associates should be able to explain how and when they get credit. If they can't, the system won't motivate anyone.

The Takeaway: Make the Right Thing the Easy Thing

Clienteling has been around as long as the little black book. What has changed is the scale retailers can pull it off at, and the expectation that every associate (not just the naturals) can do it well.

The common thread across all seven lessons is ease. Hand associates the right customer at the right moment. Put the data they need in one place. Give them time in their shift, templates to start from, and a clear picture of how they earn credit. Do that, and clienteling becomes part of how your stores run every day.

As Casey put it, clienteling gives associates a chance to take their goals into their own hands for the first time, without depending on whoever happens to walk through the door. That's a pretty good pitch for your team, too.