Bold Commerce’s Deanna Traa On Driving Checkout Conversion And Shortening The Path To Purchase

Retail Bum
6 min readFeb 22, 2022

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Winning the loyalty of today’s increasingly digital-first consumers requires brands and retailers to rethink their checkout flow. After all, consumers today expect an intuitive, seamless shopping and payment experience regardless of how and where they choose to shop. Retail Bum caught up with Retail Bum: Coming out of the holiday season, we are seeing a spike in consumers’ interest in shopping online. How do you anticipate consumers’ shopping and payment behaviors to evolve this year? CMO Deanna Traa and Leading Lights’ Rick Kenney to discuss the checkout blindspots that get in the way of conversion and what retailers can do about it.

Deanna Traa: As an industry, we have all been waiting for these “ “ moments to come out of the pandemic. The rise in social shopping, new payment methods, almost instant delivery — these shifts are continuing and they are becoming mainstream, not limited to trendsetters.

At the heart of it, there is this ongoing proliferation of how consumers want to shop. A couple of years ago, we talked about blink commerce. Innovations such as voice commerce, even social commerce and the return of the QR code, which was championed in the restaurant industry — those use cases are starting to become relevant in day-to-day life and we are finally getting to the point where there are a ton of commercial use cases driving the evolution of shopping.

Retail Bum: It is undoubtedly becoming essential for retailers to offer the right set of features, whether they are digital-only or whether they have a brick-and-mortar presence. Looking into your crystal ball, which features do you think will be vital for them to actually get shoppers to complete their checkout process?

It’s definitely an exciting time to be in the checkout space of retail, where a lot of these possibilities are unfolding.

Deanna Traa: Checkout is really the last untapped part of the shopper journey to be optimized. If you think about it, retailers have been investing at every stage of the shopper journey to improve the shopper experience. Today there are so many validation points that make the shopper think, “ oh, they know me, they know me.”

From predictive search, to dynamic content, reviews and recommendations, all these prompts along the journey are reaffirming, getting shoppers adding to cart and building a bigger basket. But once shoppers hit the checkout flow, it’s like, “you don’t know me at all.”

It’s not enough to load stored shipping and payment credentials — those are table stakes. Extending that same tailored, personalized experience from browse and discovery into the checkout is the opportunity. Today most retailers just default to a very vanilla checkout experience, and the numbers for sure show that.

One out of two shoppers who proceed into checkout, don’t complete their order. These are shoppers who show premium purchase intent, but half of them bail. It just seems crazy that that is such a huge component of what’s contributing to the broader cart abandonment dilemma and brands are going to need to address that.

Retail Bum: So, how do you think brands and retailers should go about addressing these issues?

All the fine-tuning that they do to optimize every other part of the shopper journey does not make up for the leaks and the money that they are leaving on the table at checkout.

Deanna Traa: There are two main themes. For brands today, I think there’s pain to solve for in checkout and there’s gain to be made in putting checkout somewhere else.

We very clearly see that retailers either need to upgrade the traditional checkout experience on their website to reduce friction and enable shoppers to get faster through the checkout or present the right information contextually based on what they know about the shopper.

In the case of subscriptions, it could mean something like collecting loyalty points. The point being all of these things need to be orchestrated at checkout. It’s about embedding checkout in high-traffic channels that brands are not monetizing today.

Retail Bum: According to the Checkout Benchmark* Study, of the 70% of traffic that comes through mobile, only 55% of it actually converts at checkout. What are some of the reasons you think retailers are struggling so much to get the process right on mobile?

There are so many different strategies brands and retailers can take, but it begins with personalization and tailoring those checkout experiences.

Deanna Traa: There was a time when we all thought that the answer to improving mobile checkout was responsive design, but the reality is most brands are still serving checkout one way through their desktop and mobile site. Businesses today don’t have the option on their eCommerce platform to say, “I see, the data says that we should be offering progressive checkout on mobile devices where shoppers advance through micro commitments, and a single page on desktop — so let’s serve up different formats based on device type.”

Instead, shoppers are offered a scrolling experience on mobile where they fill in all their information, hit ‘place order,’ and if something goes wrong, they are scrolling back up to find out their error. Unlike desktop, where a single page works fine because you see it all right in front of you on the larger screen size.

So what we need to be thinking about is what the checkout flow and experience should look like that is ideal for mobile, separate from desktop. On mobile, less is more — lending toward one-click experiences and easy payment access ( PayPal one touch, Apple Pay). Or taken one step further and tailored with preferred payment based on purchase history, along with BOPIS auto select based on location.

Rick Kenney: One thing that struck me is that there is no clear winner when it comes to designing the checkout flow. It absolutely depends on what you are trying to check out. What is the shopper buying? Do you have a loyalty program? Are you trying to get someone interested in subscription or at least reordering? There are so many of those micro choices. You have to get a design that works around shoppers’ requirements.

Retail Bum: Looking ahead, what approaches and solutions will be key to winning shoppers and driving conversion?

Moreover, when you have fundamental differences from one business to another relating to fulfillment, loyalty and different types of payments in the B2B and B2C world, there’s no one size fits all approach that works. Instead, the right solution has to blend all of those options.

Deanna Traa: Reducing friction and elevating the checkout experience for many retailers will take more than just adding digital wallets or a third-party one-click solution. There are “conversion boosters” that shoppers have come to expect in checkout, such as the ability to pick up in-store today, to collect loyalty points on my purchase, to use my preferred payment method, to convert a one-time purchase into a subscription or apply a promo code.

Retailers can’t afford to trade in the conversion gains that come from those features. Thus, while there is a role for a buy now button, there’s a bigger opportunity to think about how we shorten the path to purchase without trading off those conversion boosters that we’ve already built into the experience.

The Checkout Benchmark looks across millions of checkout sessions to reveal just what shoppers are doing inside checkout.

Ultimately, moving off a one-size-fits-all checkout is where retailers and brands will win. Offering tailored checkout flows based on one or more conditions, such as channel, customer segment, device type, is where conversion growth lies. It is not unlike the evolution we have seen elsewhere in the shopper journey. And with one in two shoppers dropping off during the checkout flow, it’s ripe for retailers’ attention.

Nearly Half Of Shoppers Abandon Checkout Process Before Completing It

Originally published at https://retailbum.com on February 22, 2022.

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