The area of API-first ecommerce has seen relentless optimization of the customer experience. Decreasing page load speeds, personalized shopping, and the ability to adopt other new features more quickly can all contribute to happier shoppers, and more revenue for brands.

But what happens when the conversion of experience into dollars falls at the last hurdle? At checkout, an unintuitive or outdated experience could be the difference between closed sale, and a wasted customer journey. 

Jordan Gal has been on a mission to improve online checkouts. He’s now started two businesses to address the problem. His current venture, Rally Commerce, offers a streamlined payment process that allows retailers to quickly adopt payment methods without protracted integration processes. 

On the latest episode of Martalks, Jordan joined me to discuss: 

  • the limitations of legacy ecommerce checkouts
  • prioritizing customer choice as part of an effective product strategy
  • the importance of following your nose as an entrepreneur, and trusting in the market as adjudicator of your success.

You can listen to the podcast in full here, or read on for a summary of the article.


Legacy checkouts are costing conversions 

Jordan describes legacy checkouts as ‘relics from the internet of 10 or 20 years ago’. Where there has been innovation in the shopping experiences leading up to payment, many websites still require labor-intensive processes for the shopper to complete the transaction.

“We’ve all been to online stores of retailers that we admire and like to shop with, and you start to checkout, and you’re either forced to create an account or go find your account information. 

“Then you get another step further. You manually type into form fields, first name, last name, city, state, zip, then you see your shipping options, then you come back then you have to pull out your credit card and maybe use your password manager or your form filler…

“When merchants force their shoppers to go through any form of friction around checkout, they are endangering the transaction. And then you start to look at that at scale and it is definitely having an impact on their business.”

Research by the Baymard Institute, which pulled data from 49 independent businesses and organizations, found that 70% of online carts are ditched at the payment stage. That’s a lot of business being left on the table. 

Jordan attributes this lingering problem to the ubiquity of monolithic platforms in the earlier eras of the internet. Where retailers had been accustomed to a single commerce solution, it was assumed the checkout would come as part and parcel. But as retailers progressively upgraded various stages of the customer journey, the checkout stage lagged behind. 

The ability to innovate around the payment layer thus became a competitive advantage. Jordan identifies Shopify as a platform that has taken the lead with payments.

“Because of that history, and how platforms were built, the checkout was assumed to be owned and operated by the platform. 

“These platforms grew into big businesses and complex solutions with a lot to worry about on the front end, a lot to worry about on the back end, with their app ecosystems and their agency partners’ ecosystems. The truth is their checkouts languished. They just have not innovated at that layer nearly as fast as new products on the market like a Shopify. 

“That’s why you have this very strange discrepancy where you have some of the best retailers in the world on platforms like Salesforce Commerce Cloud, Commercetools, Magento, SAP and others. Their checkouts look like they’re from 10 years ago, because they are in fact from 10 years ago.”

Rally Commerce allows retailers to “leapfrog into the present”, as an API-first checkout that can plug into other ecommerce platforms. Jordan explains that the solution streamlines the adoption of new and popular payment methods such as Apple Pay or Google Pay, that don’t require account activation, form-filling, or the storage of customer data by the retailer. 

Whereas previously integrating a new payment method would require extensive development work, Rally allows retailers to offer new options “at a click of a button”. The tech also comes with other useful functionality such as pre-populated item payment links for social media or newsletter selling, and ‘post-purchase offers’.

Enabling choice for retailers and their customers through composable checkout

Checkout can be viewed as another iteration of the tussle between monolithic and composable product strategies.

Despite praising Shopify’s checkout experience, Jordan draws a comparison with other commerce platform vendors, and their increasing willingness to embrace retailers’ preferred ways of working.

The issue with Shopify is that they’re very willing to exercise their power in defense of their business model, regardless of what the merchants want. And other platforms like Commercetools, Adobe Commerce, Salesforce and BigCommerce, they’re a lot less willing to tell the merchant what they can and can’t do. So that higher form of respect for the merchant’s decision-making is the right environment for us.

In the case of checkout, the importance of this step in the customer journey is such that it’s actually forcing brands to consider replatforming. Jordan said he’d seen a number of brands migrate to Shopify, attracted to the quality of Shopify’s checkout experience – and others, to composable platforms that gave them the freedom to choose their own checkout.

Jordan now sees an ecommerce ecosystem that is more open to collaboration with innovative vendors in this space. He explains that Rally Commerce has been able to work with legacy platform providers, SIs and agencies, and retailers themselves, to move towards a more customer-centric payment experience.

A few years ago, he explains…

“…it would have been unimaginable for Salesforce Commerce Cloud merchants to build their storefront completely off of Salesforce, and then choose a checkout that’s right for them. And then choose an order management system and a PIM and just grab these individual solutions that are just right for the merchant.

“We think that is inevitably where ecommerce goes, especially in the mid-market and enterprise levels. And we want to be part of that. And we want people to know that the checkout layer, which can be complex, and difficult to build and maintain, can be looked at as a solved problem.”

As such, Rally Commerce is ultimately agnostic as to the payment options it provides to a retailers’ customers.

Jordan describes Rally as a ‘train station’ with regards to different payment rails that users may use. Rather than prioritizing any one method over another, it only provides retailers with the functionality and choice their customer needs.

Trusting in the market as an startup entrepreneur

Checkout has been Jordan’s mission for some time. He founded another business, CartHook, in 2014. Acquired in 2021, the solution offered post-purchase offers for Shopify stores, despite initial resistance from the platform itself.

“We started off as an abandoned cart app but then we identified a bigger problem in building a better checkout for Shopify merchants. We got into a fight with Shopify, and they wouldn’t let us into the App Store.

“But we still boomed, just absolutely boomed. All through word of mouth despite never being allowed on the App Store.

“Millions in ARR, doubling every year, billions in GMV. That felt very much like we were on to something.”

Of course, fighting with incumbents comes with a degree of risk. But when you consider that Shopify has now incorporated post-purchase offers – a CartHook innovation – it’s clear this is a case study in the importance of trusting your instincts as an entrepreneur, and in your belief in the direction of the market.

“It’s rare what happened to us at CartHook. It’s rare to hit product market fit, and feel that type of pull from the market. That is addictive….

“It feels great to be an entrepreneur and to swim in a lake of risk: the upside of that, and the downside of that. The market is very honest with you, and whether it likes what you’re doing or not. If it doesn’t, then your company fails, and you start something else.”

In Rally Commerce’ case, that ‘addiction’ seems to have spread beyond the founder; many of Jordan’s best people followed him from CartHook to Rally Commerce.

This is a notable feat, in an industry where many startup founders burn out after a liquidity event, often taking some of their lieutenants down with them. It also seems to be a testament to Jordan’s leadership philosophy.

“People want to be part of it. Then you treat them fairly and you pay them fairly and you motivate them appropriately. Then you feel like you’re part of something bigger – that makes an impact directly on individual businesses and makes their businesses better and people’s jobs and lives better.”

“To me, entrepreneurship is just this very obvious force for good. And I feel lucky to be in a position to lead a company.”

About The Rosenstein Group

The Martalks Podcast publishes fresh content monthly about martech, commercial strategy, entrepreneurship and startup scaling.

Our earlier piece, on scaling a startup during an investment downturn, gives other examples of startup founders whose leadership approach has been fundamental to the company’s success.

The Martalks Podcast is published by The Rosenstein Group, the leader in martech executive search. For over 20 years, we’ve been recruiting heads of sales, channel sales leaders, and other members of the commercial team, across martech, supply chain, ecommerce, sales enablement and systems integration.

Visit to find out more.

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