Perfecting Personalized Promotions, The secret to achieving advanced personalization, and what’s holding retailers back

Promotions are a key performance area for all retailers, and effectively implementing truly personalized offers at scale has been a goal for enterprise retailers for decades. Eagle Eye’s CRO Jeff Baskin shares his thoughts on how technology is making this goal more attainable, the legacy approaches that are holding retailers back, and what impacts they can expect from genuine one-to-one promotional engagement.  

The biggest flaw with traditional mass discounting is that it often incentivizes customers who would have purchased anyway, while failing to influence behavior where it matters. This inefficiency is largely driven by legacy systems and the inertia of “what’s always worked.” Most retail infrastructure was built to support blanket offers or, at best, broadly segmented campaigns, not individualized promotions at scale. For years, that was effective, but as competition intensifies and technology improves, more retailers are embracing approaches that enable one-to-one engagement. After all, dynamically creating an offer for the exact brand of organic snacks the individual customer is most likely to respond to at the exact discount level most likely to prompt them to action is inherently more effective – and efficient – than placing a generic discount on similar items in the weekly circular.    

Manual processes, unstructured data, and legacy platforms are the main roadblocks to true one-to-one personalization and are what keep retailers relying on broad-based approaches. There are also two issues of scale: first, the volume of data (customer data, SKUs, multiple sales channel data) retailers must manage has increased exponentially; and second, the ability to deploy personalized offers at enterprise level across millions of transactions remains out of reach. Few incumbent promotional systems support the real-time decisioning or on-the-fly offer creation necessary to deliver unique promotions to individual customers across a multi-store network, let alone a portfolio of banners.  

From a tech perspective, AI and machine learning models can now analyze behavior and generate custom offers in milliseconds. Cloud infrastructure handles the computational demands of real-time adjudication across millions of shoppers or loyalty members. Operationally, retailers now have the customer data and digital touchpoints necessary to identify individual shoppers and deliver offers at checkout, online and in-app. These two components are equally important; even the most advanced AI will deliver irrelevant promotions without data-based insights into what individual customers care about, and all the customer data in the world is useless without the technology make it actionable. 

Attribution at the individual shopper level is essential. You need systems that track each customer's baseline purchasing patterns, then measure how behavior changes when specific offers are delivered. Closed-loop reporting that connects offer allocation, redemption, and actual sales lift reveals which promotions are working. Of course, this requires technology that follows the complete customer journey from offer to purchase, across platforms and channels, and incorporating both marketing-exclusive systems (like retail media networks) and traditionally analog interaction points (like physical stores). 

BCG estimates enterprise retailers can generate over $100 million in topline impact from scaling personalized offer execution. That suggests that retailers’ current promotional spending is underperforming, delivering little incremental value for the budget. It tells us that when retailers offer undifferentiated incentives to customers with existing purchase intent, or offer deeper discounts than necessary to change behavior, they’re essentially paying for sales they already had. 

Customers now expect offers that reflect their actual shopping behavior; generic discounts feel irrelevant. In this way, promotions have become a de facto indicator of whether retailers truly understand their customers. Those who do can deliver timely, meaningful incentives, build stronger engagement and capture more share of wallet. Those who don't risk spending promotional dollars with little measurable return. In a marketplace with more choice than ever, relevance is a clear competitive advantage. 

Personalization ensures that customers receive offers that feel relevant and appropriate rather than random or excessive. When offers align with consumers’ actual preferences, purchase patterns and contextual cues, engagement naturally increases. Delivered through digital channels or at checkout in the moment of decision, personalized incentives create a higher-value experience that encourages repeat behavior and strengthens ongoing loyalty. They also drive results for retailers; Eagle Eye’s AI-powered Personalized Challenges, which creates personalized, incremental goals for each shopper based on their purchase history, has generated 7:1 ROI for high-profile retailers that have implemented the solution