Holiday Shopping 2022: How AI-Powered Guided Selling Creates Bespoke Customer Experiences

With the holiday season on the horizon, brands are looking to gain an advantage over industry competition. Considering many customers will be buying some, if not all, of their holiday gifts online, identifying ways to capitalize on increased ecommerce demand can make or break an organization’s holiday profit potential. As the state of retail technology advances, companies are learning how to leverage artificial intelligence (AI) and machine learning (ML) tools to provide more bespoke shopping experiences online.

In any omnichannel approach to sales, it is essential to look at how to replicate the best parts of an in-store experience online. Online retailers are always looking for ways to simulate guided selling — the process where a sales associate engages a customer about their specific needs and guides them to the perfect item without further browsing or research. This simple tool for a website can be implemented even after code freeze, adding a reactive and engaging layer to the online shopping experience. By employing AI-powered technology, the guided selling process can now be enhanced and streamlined through the power of automation.

Beyond the transaction itself, guided selling provides brands with data that can lead to a deeper and more intuitive understanding of their consumers. Learning how customers respond to specific product recommendations enables brands to understand better what consumers are looking for and why. The real-time visibility allows them to construct their offerings around what items are being shopped for more often, what product upgrades are most attractive, and what factors are most important to determining the customer’s final purchasing decision.

The Quickest Path to the Perfect Product

Guided selling is an interactive method for helping customers quickly identify the product that is right for them. In industries like apparel or electronics, where specific sizes, brands and types make all the difference, having a tool to reduce the research time required by the customer makes for a more seamless customer experience. For example, a customer purchasing Bluetooth or wireless speakers doesn’t want to waste time cross-referencing sizing or compatibility specs for every product available. Their purchasing decision will be influenced by convenience and relevancy.


AI-driven guided selling can be accomplished in several different ways. First, it requires adopting a dynamic ecommerce platform that can engage customers in real-time, asking questions relevant to identifying the item they are interested in. Organizations can set up a flow of questions that build upon each other to present personalized product recommendations or lead a customer to the single product that is best for them. The end result is a selection or series of selections, that feel personalized for the buyer. Shoppers arrive at their desired product faster and more confident that it being the right item for them.

Benefits for Both Customer and Company

The benefits of guided selling are clear. A more streamlined experience that leads to smart purchasing decisions is a crucial driver of consumer brand loyalty. Evidence suggests that in the near future, high-quality customer experiences will overtake product quality and price as the most critical factor in differentiating between brands.

Implementing AI-powered guided selling tools within an ecommerce platform enables brands to reduce choice paralysis and shopping fatigue, leading to higher conversion rates and happier customers. In order for brands to stand out against their competition this holiday season, the focus needs to be squarely on the customer experience. Guided selling will soon no longer be a fun option for brands to stand out in their field but a required practice to provide the best online service available. The 2022 Omnichannel Retail Index shows that only 26% of retailers offer guided selling, thus allowing several retailers the opportunity to stand out this holiday season.

Want more insights from the 2022 Omnichannel Retail Index to guide your 2023 strategies and tactics? Watch our recent webinar featuring Bernardine Wu of OSF Digital and Rob Garf of Salesforce now!

Kathy Kimple is the Executive Director of OSF Digital’s Strategy group. She leverages 25+ years in omnichannel retail with a focus on brands, covering digital strategy and store operations, registry, marketing, tech selection, and organizational design.

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