Report

Conversational Commerce for the holidays: A digital retail wish guide

Brian Donnelly headshot

Brian Donnelly

July 16, 2021

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9 minutes

e-Commerce chatbot assisting a shopper over text messaging

In the last year, retailers have had to show what they’re made of. They’ve been nimble, resilient, and most importantly, willing to change. They quickly built curbside pickup models to keep employees and customers safe. They got creative with new tools like line spacers and QR codes. They enhanced their digital capabilities — some built out digital commerce for the first time, while others fully pivoted to a digital-first model with solutions like Conversational AI for retail. And that was just to keep up the status quo. 

<kicker-title>When it came to the holiday season, there was lots of cheer, shopping, and even more curveballs:<kicker-title>

  • Retailers geared up for a digital Black Friday, only to be thwarted by an unexpected Q4 Amazon Prime Day. The surprise move had cash registers ringing in a holiday shopping season that started in early November. 
  • As orders came in, retailers struggled to deliver on customer service, as pandemic-related fulfillment issues plagued the industry. 
  • But that didn't prevent a record-breaking year in digital commerce, with the US alone exceeding the $1T mark for the first time.

With the consumer economy making a comeback in 2021, digital commerce remains optimistic. But where will we find shoppers come November? Will lingering memories of fulfillment mishaps drive them back to stores for instant gratification? Or will emerging restrictions around third-party cookies hamper the digital customer experience, further reversing the online migration? 

Turns out the year after a pandemic-driven lockdown is just as unpredictable and (say it with us) “unprecedented” as the lockdown itself. Even Amazon Prime Day 2021 didn’t paint a clear picture of what to expect. Yes, Amazon broke a new record with over 11BN in sales, but the increase from 2020 was around 6%, whereas in the previous 4 years of the shopping holiday, the company has seen minimum 45% increases YOY

Good news: It looks like consumers continue to be excited about digital commerce. 

Confusing news: It’s going to be tough to predict online shopping volumes in the 2021 holiday season.

Never fear — we have some thoughts on how to succeed, leveraging lessons from the pandemic. Read on or open the printable version.

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<blog-number>01<blog-number> Continue to blur the lines between online and offline to solve fulfillment issues while remaining contactless

Woman placing BOPIS purchases in her car


The emergence of curbside pickup and BOPIS (Buy online; Pick up in store — sometimes called Click-and-collect) created a hybrid fulfillment model that solves for challenges in many ways, while adhering to contactless consumer behavior that may persist throughout a cold winter. Although the pandemic accelerated the need for this model, it’s been a long time coming.

Let’s roll back to pre-pandemic times. In 2019, many online shoppers chose to bypass delivery periods by opting for in-store pickup with a record 43% increase in customers choosing this option. In the US alone in 2020, BOPIS or Click-and-collect more than doubled, with industry experts projecting another 15%+ in growth in 2021.

Even without the pandemic, the winners were the retailers who most successfully navigated the online-to-offline experience. For example, Forbes lauded Walmart and Target for “their omni-channel strategies, wide product assortments, strong mobile shopping platforms, and BOPIS offerings.” As of 2020, what was once a trend for convenience became all but necessary. 

Now that demand for these low-touch digital customer experiences are here to stay, the onus is on retailers to make sure they build experiences that are seamless and efficient, drive additional ROI, and add value to the shopping journey. For example, bringing Conversational AI to the curbside pickup experience will make the process more convenient and streamlined.

<kicker-title>With a conversational curbside pickup experience:<kicker-title>

  1. Customers pull up to a parking spot and scan a unique QR code.
  2. They interact with a bot within mobile messaging that confirms information like order number. 
  3. Then customers simply wait in their car for an associate to bring out their order with a persistent channel open for status updates or other communication.

Brands can take similar measures to a true in-store shopping experience, leveraging Conversational AI activated by QR codes to create opportunities for virtual in-store support from remote associates while shopping or standing in line. 

Shopper scanning QR code for virtual assistance while in store

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<blog-number>02<blog-number> Provide comparable purchase guidance to both digital shoppers and in-store shoppers

Typical web conversion rates hover pretty low — around 3% normally, and holiday cheer doesn’t make things any better, hovering around 4%. There are a number of “Bah humbug” factors at play here, like disjointed checkout experiences, lack of sales support, and difficult discovery journeys. By rooting your digital operations in a messaging strategy backed with automation and machine learning, you will be able to increase these conversion rates by recreating key elements of the in-store experience over web or mobile messaging channels. AI-powered e-Commerce chatbots and specialized agents combine to help customers pass common barriers to conversion.

Brands can see as much as a 4x conversion rate and a 1.75x increase in average order value with messaging-assisted sales


<kicker-title>But Conversational AI for retail can go far beyond sales and care support:<kicker-title>

Pretty much anything you can do in a store, you can recreate in a digital capacity via messaging. For example, a jewelry company can provide personal stylists, proactive outreach for special occasions and reminders, virtual showrooms and try-ons, video appointments, and more — all from a customer’s favorite messaging channel. A major jewelry retailer has big plans to take on this exact challenge after they saw $50M in incremental revenue attributed to messaging-assisted sales in just 6 months (and that’s during a pandemic!).

Similar to how holiday shopping can bring a lot of extra foot traffic to your stores, you’re likely to see some massive (if somewhat hard to predict) surges in digital volume as well. Just like you would hire seasonal employees to help cover shifts and manage increased volume, Conversational AI can help you manage fluctuations in sales and service demands. For hands-on assistance building out your program, LivePerson’s contact center as a service (CCaaS) is a managed solution that offers “surge protection” so that your brand is ready for anything.


Tailored to a brand’s needs and desired outcomes, the managed contact center solution has a simple, outcome-based pricing model and can range from a seamless extension of existing operations to a full end-to-end alternative. The solution runs on LivePerson’s AI-powered Conversational Cloud and leverages customer intent data. Customer intent is effectively the reason why someone is contacting your business, and it’s a powerful source of first-party data that can be used to build and tune bots that answer top questions quickly and to train a distributed network of live agents to assist with complex or sensitive matters. 

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<blog-number>03<blog-number> Rethink personalization in a cookieless world to continue to deliver differentiating digital experiences

(Don't worry, we're not talking about holiday cookies — those are here to stay)

Conversational AI for retail isn’t just a “little helper” for the holiday season; it will benefit your brand year-round. But something that COVID-19 showed us is that understanding why customers are coming to your brand is critical to operations and your automation strategy. This means going beyond superficial clicks, hovers, and third-party data to figure out what your customers want. And it’s probably for the best — with our impending cookieless future, that kind of third-party data is going to be harder and harder to come by in the first place. 

As marketing, sales, and care leaders, it can be easy to see the ever-changing shifts in data privacy and security as blockers for personalization. But instead, we encourage marketers to think of privacy as a key piece of segmentation data. By understanding and respecting customers’ wishes, you’re likely to build more lasting relationships with higher lifetime value. 

The best way to understand this “why” is by asking

Text messaging conversation where retailer gathers and gets permission to use first-party data


Many brands are turning to customer intent data to drive their business decisions. For retail, the most common consumer intents are to ask about store inventory, initiate a return, and get information about a product, along with many others. Intent data is gleaned from conversations between customers and brands, and they are inherently consensual, two-way exchanges through which customers willingly share crucial first-party data. But the real power is how you apply that first-party data to both the interaction with the individual customer and to better your business practices overall. 

Applying intent data can come in many forms. For example, in April 2020, 22% of retail customer outreach was around "order status" (up from 13% in Feb 2020/Pre-pandemic). By analyzing this type of data, brands can contain these conversations with automation, freeing up agents to handle more novel and complex queries — namely those that drive revenue.

<kicker-title>Real-life example:<kicker-title>

One US-based retailer dove into their inordinately high volume of “returns” intents. In their search they realized that many of the inquiries actually had to do with exchanges rather than returns. Because exchanges required a different process, customers were getting stuck when they were served a “returns” automation flow. Using this information, the brand was able to build a new intent and bot flow specifically for exchanges, greatly impacting their customer experience and ultimately their bottom line.

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A final wish for the holiday shopping season

Leading up to this holiday season, retailers have an opportunity to put these innovative practices in place that will benefit them year-round. Conversational AI and messaging will be critical for this digital transformation — from coordinating seamless fulfillment to creating rich digital experiences in channels customers love, gathering and applying customer intent data to your business, and more.

Dig deeper into LivePerson's Conversational Commerce and Conversational AI for retail solutions, or request a demo below.