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Implementing a clienteling strategy in a luxury retail store, especially in the jewelry industry, requires careful planning, leadership, and team buy-in. Many store owners struggle with the challenges of adopting new technology, training their teams, and ensuring long-term engagement.
Bob Woolsey, President of Jones Bros. Jewelers in Illinois, shares his insights on overcoming these obstacles based on his experience with Clientbook and other retail technologies.
1. Start with early adopters and just get started
One of the biggest hurdles retailers face when introducing new clienteling systems is simply getting started. Woolsey advises store owners not to overthink the process:
"Test it out with other people in the industry and see how good it is. From there, find the most tech-savvy people at your store and have them be the early adopters to try it first. Then have them help the rest of your staff and get it implemented across the whole store," he says.
When Jones Bros. Jewelers adopted Clientbook, the digital sales assistant for luxury retailers, they took a straightforward approach. "We just launched it at one point and got it going. So don’t paralyze yourself with perfection when you first get going. Just get started and learn as you go."
This approach helps prevent delays caused by over-planning and allows the team to adjust and improve as they go.
2. Training that fits the sales environment
Training staff on new technology can be a challenge, especially when balancing time on and off the sales floor. Woolsey believes that hands-on experience is the best teacher, especially with Clientbook.
"With Clientbook, it’s pretty intuitive. We let people run with it. The main training will be how do we utilize sales opportunities, or tags, or processes so that everyone’s doing the same thing," he explains. "For tech-savvy people, it’s pretty simple."
To support training, Jones Bros. Jewelers provides videos and a sandbox account for their point-of-sale system so employees can explore the tools on their own. However, Woolsey emphasizes that the most effective learning happens in real customer interactions.
"Until a sales associate is in front of a customer, they’re not going to fully learn anything. When they’re on the floor with a customer, that’s where the real learning happens. When you’re entering in a real sale, or a real repair, and you have a living, breathing person there, it makes all the difference. Because there’s a different level of pressure that they have to deal with."
3. Creating time and space for training
While learning on the job is the best teacher, your sales associates have to start somewhere. That’s why Woolsey highlights the importance of providing dedicated training space.
"We recently put in a conference room that allows us to do training off the floor, and it’s been a game-changer. It’s hard to do training in front of the customer unless you have a place to go," he shares.
While on-the-job training remains crucial, having a dedicated space to practice new tools without the pressure of live transactions can significantly boost adoption.
4. Evaluating technology before investing
Selecting the right clienteling software is another critical step. Woolsey relies on insights from other jewelers before making technology decisions.
"If a new technology comes out that I’m interested in, I’ll reach out to groups that I trust, or jump in a chat or discussion group online. Buying groups are another great resource," he explains.
He warns against relying solely on sales pitches. "The salespeople from those technology groups are always going to make their technology sound like it will solve every problem for you—it’s their job. But when you hear from real jewelers in the industry on what’s good and what’s not, you know you’re getting good information."
5. Driving team buy-in
Finally, for any new tool to succeed, employees must see its value. Woolsey believes that the key to securing buy-in is demonstrating how the technology benefits them.
"The first piece is selling the benefits. How does it help them make money? How does it make their job easier? How does it make their customers’ lives better?" he says.
If employees resist the change, store owners should dig deeper. "If there’s still pushback after you’ve communicated the benefits, find out what the heart of the problem is. What’s really holding them back may not be what you think. It might be a concern of ‘I’ve always done it this way,’ or some people are just wired for something not to work."
By addressing these concerns through open conversations, retailers can turn skepticism into enthusiasm.
6. Embracing AI in retail
Looking ahead, Woolsey sees artificial intelligence as a transformative force in the retail industry.
"I think AI is the next industrial revolution. We all have to figure out our best uses of it and don’t be afraid. It’s not going to fully replace a human being," he says.
At Jones Bros. Jewelers, AI-powered tools like Clientbook’s AI Insights are already proving valuable. "AI Insights in Clientbook gives ideas for clients to reach out to that you hadn’t thought of. I’ve talked with other jewelers who use it even more than I do, and they’ve talked about how it starts to really respond more and more every day like your people and your store. It really learns, which is so cool."
Beyond clienteling, Woolsey also sees AI streamlining administrative tasks. "ChatGPT is really cool for simple things that take time like planning a meeting and sales training. The more you put in, the more it puts out. Simple contracts or even marketing stuff it can do a good job with. Or job postings and descriptions are great with AI—any of that manual employee stuff."
However, he stresses the need for oversight: "The main thing with AI you have to do is watch it and make sure it’s in line with your brand, your values, and the messages you want to send."
Conclusion
Successfully implementing a clienteling strategy requires more than just adopting new technology—it demands strong leadership, hands-on training, and a focus on team engagement. By leveraging early adopters, creating effective training environments, ensuring team buy-in, and embracing AI, store owners can navigate the challenges of change and set their businesses up for long-term success.
As Woolsey’s experience with Clientbook shows, the key is to take the leap, learn along the way, and always prioritize what benefits both the staff and the customers. If you’re ready to start implementing a clienteling strategy with Clientbook, book a demo to get started.
