Hiring an AI Leader in Retail Is Uncharted Territory. Here’s the Map.

Retail has been here before. Twenty-five years ago, companies knew eCommerce would change the game, but there was no established playbook for hiring a leader to build out the new function. So, brands did what they could, pulling executive talent with catalogue experience, and adapted as the role evolved. Today, retail is facing a similar challenge with AI leadership. Every retailer recognizes the need for AI expertise, yet few have clarity on exactly what the role should look like. This presents a unique challenge. How do you hire a seasoned AI leader with retail experience when there are none? Here’s our approach. 

AI Leadership is Still Forming 

Across industries, the urgency to hire AI leadership is undeniable. Yet without a proven blueprint, many organizations are still defining the role in real time, often leading to longer, more frustrating search processes. A common mistake is attempting to consolidate too many responsibilities into a single hire: strategic vision, technical expertise, operational execution, and enterprise-wide influence. In practice, this scope exceeds what one executive can effectively deliver. The right profile depends on the organization’s priorities. As a result, the best hire might come from a range of backgrounds. The critical first step is for the organization to define their priorities and then align the role to match. 

The Retail Challenge 

The retail industry faces another layer of complexity. AI is transforming nearly every aspect of the business, from customer experience to supply chain operations. On the customer-facing side, AI is the key to improving personalization, loyalty programs, recommendation engines, and augmented reality experiences. On the operational side, AI is shifting merchandising, inventory management, forecasting, distribution, and supply chain optimization. Because the scope of influence is so broad, retailers often discover they will need more than one AI executive to oversee all their AI needs. Ultimately, the most successful organizations will treat AI as a business initiative supported by technology, not an IT project searching for business adoption. Internal alignment around priorities, ownership, and desired outcomes is critical before any hiring process begins. 

Key AI Leadership Profiles in Retail 

Three AI leadership profiles are beginning to emerge:  

1. The Technical AI Leader 

Executives that typically come from data science, machine learning, analytics, software engineering, or AI infrastructure backgrounds. They own the data ecosystem, governance, engineering, and deployment capabilities that enable AI at scale.  

2. The AI Transformation Leader  

Executives that often come from digital transformation, strategy, consulting, or general management backgrounds. They focus on prioritization, adoption, change management, and aligning AI investments with business objectives.  

3. The AI Product Leader 

Executives that come from product management and innovation functions. These executives sit between business and technology teams to build, prioritize, and scale AI-enabled products and solutions. While still relatively new, the emergence of this role reflects the growing maturity of enterprise AI programs. 

Increasingly, companies are pairing the first two profiles, the technical AI leader and AI transformation leader, recognizing that technical execution and business transformation require different skill sets. The third profile, the AI product leader, is largely only found in mature, scaled organizations, which require additional leadership on top of the technical and transformation profiles. 

The lesson for retail leaders is straightforward: stop searching for the perfect AI executive. That person likely doesn’t exist. Instead, start by defining the business problem you’re trying to solve, determine whether you need technical leadership, transformation leadership, or both, and build the role accordingly. Just as retailers once learned how to build eCommerce leadership from adjacent talent pools, the next generation of AI leaders will come from multiple backgrounds. Retailers that recognize this reality and hire accordingly will be the ones that most effectively leverage AI as a competitive advantage.