Jon Cleaver, Chief Technology Officer at SportsShoes.com, has spent over 20 years leading technology transformation across retail and ecommerce. He leads the online retailer’s technology strategy, helping shape the systems, processes, and innovations that support the next phase of the business’s growth.
Cleaver shared his perspective on the future of retail, the lessons learned from SportsShoes.com’s digital transformation, and why building the right technology foundations is key to long-term success. “You don’t really know how customers are going to interact with new technology until you put it in front of them. That’s why they test, learn and refine,” he said.
Background and Experience
Cleaver has spent more than 20 years working in retail technology, leading digital transformation programs across a range of businesses. He joined SportsShoes.com four years ago as Chief Technology Officer, and since then, the company has been on a significant transformation journey, modernizing its ecommerce platform with a flexible architecture.
Cleaver emphasized that successful transformation is as much about people as it is about technology. “You can have the best platform in the world, but unless you bring the business with you and solve real problems for customers and your teams, you’re never going to get the full value from it,” he said.
His extensive experience in retail technology has also taught him the importance of understanding the customer’s perspective, and how this understanding can inform the development of effective technology solutions. By putting the customer at the forefront of the transformation journey, Cleaver has been able to drive meaningful change and improvement in the business.
Technology Approach
SportsShoes.com’s approach has always been to build the right foundations first. Moving to BigCommerce and adopting a flexible architecture has given the company a technology platform that can evolve alongside the business. Cleaver noted that the biggest advantage is flexibility, allowing the company to introduce new capabilities more quickly and respond faster to changing customer expectations.
The company has already seen the commercial impact of this approach, achieving a significant increase in conversion since modernizing its ecommerce platform. Cleaver said that success isn’t a one-off milestone, but rather creating a platform that allows the company to keep moving forward.
This approach has also enabled SportsShoes.com to experiment with new technologies and innovations, such as AI-powered product discovery, and to refine them based on real customer behavior. By taking a flexible and adaptable approach to technology, the company has been able to stay ahead of the curve and respond to changing customer needs.
Measuring Success and Best Practice
Cleaver said that measuring success starts with the customer, looking at commercial metrics like conversion, as well as how quickly the company can introduce new capabilities and respond to customer feedback. He emphasized that best practice is about being prepared to experiment and understanding how customers actually shop.
SportsShoes.com has been testing AI-powered product discovery and analyzing how customers interact with it. Cleaver said that having accurate, well-structured product data will become even more important as AI and technologies like agentic commerce continue to evolve.
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In addition to experimenting with new technologies, Cleaver also highlighted the importance of reviewing product data through the customer’s lens. By understanding how customers search for and discover products, SportsShoes.com has been able to improve the way it structures its product data and make better-informed decisions about where to invest.
Partnerships and Future Plans
SportsShoes.com partners with specialist technology companies, including Feedonomics and Bloomreach, to deliver a better customer experience. Cleaver said that the ability to integrate these technologies together has been a key part of the company’s transformation.
Looking ahead, SportsShoes.com will continue its transformation journey, applying the same thinking across the rest of the business. The company will also explore where AI can deliver genuine value, taking a measured approach by testing new ideas, learning from customers, and investing where it can see a clear benefit.
As the retail industry continues to evolve, Cleaver noted that building a modern, flexible technology stack has given SportsShoes.com the freedom to keep innovating without having to reinvent everything each time the industry changes. The company will continue to test, learn, and evolve, because that’s what retail has always been about.
It is about growth.
Cleaver leads the online retailer’s technology strategy.
SportsShoes.com has been on a significant transformation journey.
The company has already seen the commercial impact of this approach.
Cleaver said that success isn’t a one-off milestone.
SportsShoes.com will continue its transformation journey.
