In this episode of The Voice of Retail, I sit down with my friend and colleague Tara Conway — retail leader, customer experience expert and co-founder of new media property Commerce Rewired. From clienteling innovation in Babies “R” Us to executive leadership at The Source to helping us understand AI-powered inventory planning, Tara breaks down where artificial intelligence is delivering real value — and where it’s just hype. We debate retail media, workforce disruption, leadership in the age of AI, and why remarkable retailers must shed legacy thinking to win in 2026 and beyond.
In this episode of The Voice of Retail, Michael LeBlanc sits down with Tara Conway, retail strategist and co-founder of Commerce Rewired, for a wide-ranging discussion on AI in retail, digital transformation, customer experience innovation and leadership in an era of disruption.
Tara’s retail career spans decades — from growing up in a family general store to senior leadership roles at Blacks Photography, Toys “R” Us Canada and The Source. She shares behind-the-scenes insights from launching Toys “R” Us Canada’s first e-commerce site — a testing ground for global digital strategy — and implementing early clienteling technology that connected store associates with online product data, fundamentally reshaping the omnichannel experience for new parents at Babies “R” Us.
The conversation turns to artificial intelligence in retail. Tara identifies inventory optimization, assortment planning and data-driven merchandising as the most impactful AI use cases today. With thousands of SKUs across hundreds of stores, AI enables retailers to interpret complex patterns in seasonality, demand forecasting and aged inventory — decisions that humans alone struggle to process at scale.
On the customer-facing side, Tara discusses the evolution of chatbots into intelligent AI assistants capable of handling low-touch service inquiries such as order tracking and product availability. Rather than replacing employees, she argues that AI should enhance workforce productivity by eliminating repetitive tasks and enabling leaders to focus on higher-value decision-making.
The episode also explores the risks of retail media networks. Tara warns that retail media can quickly become a friction point if revenue generation outweighs customer experience. Success, she argues, depends on intent: using data and messaging to improve the shopper journey, not overwhelm it.
Michael and Tara debate why smaller and mid-sized retailers often outpace large chains in digital agility. Without legacy systems and bureaucratic layers, emerging brands can implement rapid test-and-learn strategies that drive innovation visible to consumers. For larger retailers, shedding outdated processes and shortening decision cycles will be critical to remaining competitive.
The episode closes with Tara introducing Commerce Rewired, a new media platform focused on bold debate, data-driven insights and candid conversations about the future of commerce.
For retailers navigating AI adoption, workforce transformation, omnichannel strategy and digital innovation, this episode delivers both strategic clarity and practical perspective.