October 13th, 2025: Process Re-Engineering Is a Key Skill in the Age of AI, Stripe Link Moving More Consumer Facing, Is OpenAI Building a Super App? And Shopify CRO Bobby Morrison Forced Out
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It’s October 13, 2025 and this is the Watson Weekly - your essential eCommerce Digest!
Today on our show:
Process Re-Engineering Is a Key Skill in the Age of AI
Stripe Link Moving More Consumer Facing
Is OpenAI Building a Super App?
Shopify CRO Bobby Morrison Forced Out
- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.
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To hear new episodes of the show every Monday morning, subscribe now at rmwcommerce.com/watsonweekly and wherever you get your podcasts.
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[PAUSE]
BUT FIRST in our shopping cart full of news….
Process Re-Engineering Is a Key Skill in the Age of AI
I recently had a conversation with Jason Cottrell that will release on the Oh Shift! podcast soon, and he was speaking about an employee progression metric (adapted and derived from Zapier) where the last stage is "Transformative". At Orium this means that AI is not just saving time in an existing process, but that processes have been totally rethought between departments with AI in mind.
Sounds simple right? No.
In general I would say that process re-engineering is one of the most difficult forms of leadership, period.
For most people, the answer is always: see tool, buy tool. Hope for the best.
But if the tool fails, find better tool is usually the answer rather than figure out what went wrong.
Sometimes the problem is that people aren't communicating with each other. Sometimes people don't want to rethink what they've been doing. And that's exactly why some kind of employee measurement framework is required. Even essential.
It sets a challenge. What's the challenge to employees then?
Simple. Business as usual is not acceptable. Processes need to be looked at from first principles with fresh eyes, with a keen eye toward customer outcomes.
And look, a lot of people aren't willing to go there. Perhaps that's why you see some of the studies you do now. But suffice to say, companies that do look at critical revenue processes will be the winners in this era.
Not just companies who encourage employees to "try AI first". How do you measure what's working? What are your value metrics? To do that, you need to look deeper than the surface vanity demo.
>> closer
[References:]
Our Second Story
Stripe Link Moving on Up
While Stripe Link has been quiet for a long time, it does appear that the profile of the payment method is increasing. Stripe is hiring for a Head of Consumer Marketing for Link on its website.
Reported facts include:
* Over 100 million consumers
* Millions more joining the network each month
That compares to 200M+ Shop Pay users (as reported in Feb by Shopify). It seems to me that Stripe Link is growing about 2x slower than Shop Pay -- at least on an order of magnitude -- and that Stripe would like to accelerate that.
While I can compare it to Shop Pay here, the real issue is Paypal. With a consumer-facing arm, Paypal has many more weapons to win a long-term war than Stripe does. So Stripe Link growth rates matter.
However, Stripe and Shopify and Paypal while overlapping and all are competing, they are also not 100% in competition -- likely all CEOs feel there can be multiple winners here.... so again, growth rates matter.
And while Paypal Branded Checkout is growing much slower than Shopify, it's also growing slower than Stripe Link too. Meaning ... Stripe wouldn't mind increasing its growth rate here.
Over the long term if you are close to the consumer you have more opportunities to increase your margin through ads, lending and other means than the alternative.
“Why It Happened or What’s Happening Next? Or What’s Interesting? Strategic? Etc
>> closer
[References:]
Our Third Story
Is OpenAI Building a Super App?
I attracted some maybe negative attention from some of my listeners this week when I insinuated that OpenAI was building a real Super app in the West the likes of which we maybe haven’t seen recently.
The Western world has chased the idea of a Superapp for many years - trying to recreate Wechat in the west, the Chinese social media, messaging, and wallet app owned by Tencent. Within Wechat are many "mini-programs" which exists from Didi (cars) to bike sharing to paying for utilities.
Yesterday, the CTO of Instacart announced they are partnering with OpenAI on Apps within ChatGPT which looked interesting. One of the more interesting screenshots (we will see in a few months the usefulness) I've seen in a while. But will it cook?
What's a SuperApp?
The corporate vision is to be the toll collector for everything - more expansive than even the mobile app stores. Many companies in the United States have professed to be building super-apps. From X to Square/Block and more. Even Klarna and Bolt have mentioned the idea in the last year. Most is just marketing hype.
But no one has the potential to pull it off like OpenAI. The success of OpenAI becoming a superapp depends on a few things:
1 - Incentives for the developers. The "vig" from OpenAI needs to be not so onerous as to discourage innovation. Apps must be easily promotable and the app store must be seamlessly integrated with the experience. (read: Ads are eventually coming here too)
2 - User ease. This is a big one. The flow has to be natural for users, such that it doesn't require special code words or awkward things you type to activate the usefulness of the app. Think about the Alexa app store as the worst example of this. Technically it works, but practically it's painful. LLMs have the promise of making it easy.
3 - Network effects. More users attract more app developers. More app developers build more apps. More apps means greater chance of useful apps. Useful apps attract more users.
What would kill such a super app opportunity?
- It's too clunky. Language is imprecise, which could make it hard to use or find apps.
- Early app failures. Big early wins could help fuel the effort. Big notable failures could cool off the effort.
- Competition. Someone like Apple or Google who already has apps. Are they thinking this way? Hard to tell. Counting out Apple never a good idea. They are one of the best fast-followers in the world when a big new idea hits the stage and is clunky as hell to use. Few have the user obsession that Apple has. To OpenAI's credit, they do recognize this. But with Jonny Ive really working on hardware, will it get much of his time?
Lots of questions, few answers at this stage. But the ambition makes it one to watch.
[References:]
[PAUSE]
And Our Last Story
Shopify CRO Bobby Morrison Forced Out
Let's follow the chain for a second right?
1 - Kaz left to join OpenDoor as CEO, and this seemed to expose Bobby, who was the buffer between Bobby and Tobi. (fact)
2 - Bobby got a new buffer - Jess. (fact)
3 - Jess was not happy with what she learned? (speculation)
4 - Bobby presents to 8k people at Netsuite SuiteWorld this week on behalf of Shopify. (fact)
5 - Jess was promoted to COO based on her prior work, and what she learned needed to be fixed. (fact)
6 - Jess was promoted without an external search? (speculation)
7 - No thank you messages from Tobi, Harley, or Jess to Bobby. (fact)
8 - Bobby was forced out, along with a couple of top lieutenants. (informed speculation)
Some other meta-conclusions:
- Kaz seemed to be a big Bobby fan (informed speculation)
- Enterprise team missing numbers? (informed speculation)
Just saying, you don't get rid of a CRO who is knocking the cover off the ball.
Shopify momentum is Shopify momentum that is not going to change, but it does highlight that Shopify is quick to rectify what it thinks are mistakes and right the ship. I can think of 3 big ones in the last 5 years.
Allan Leinwand as CTO, unwound and reset.
Bobby Morrison as CRO, now unwound and we will see how it resets.
Huge Logistics bet, unwound and reset.
There are a lot of great people in the GTM team at Shopify, a lot of them brought in by Bobby. There were also some notable departures in the last 6 months.
And the final informed speculation: Shopify believed there were more sales and marketing departures to come if this was not done.
I'm not passing judgment on it, it's just the thing of it.
[References:]
https://www.linkedin.com/video/live/urn:li:ugcPost:7382107240851427328/
https://www.linkedin.com/feed/update/urn:li:activity:7382386549944123392/
It’s That Time Friends, for our Investor Minute. We have 5 items on the menu today.
First
Salesforce to Acquire Regrello
Salesforce has announced that it has acquired Regrello, an AI platform designed to streamline and automate complex workflows in manufacturing and supply chain for an undisclosed price. The software will be integrated into Salesforce's Agentforce platform and Slack.
Second
Pylon Secures $31M in Series B Funding
B2B customer support platform Pylon announced that it has raised $31 million in Series B funding that will be invested in product development and hiring.
Third
Klaviyo Acquires Gatsby
Klaviyo announced that it has acquired Gatsby, a social automation platform that converts social media engagement into owned customer relationships for an undisclosed price.
Link: https://www.klaviyo.com/newsroom/gatsby-acquisition
Fourth
Blue Yonder Acquires Optoro to Further Transform Returns Management and Extend Capabilities
Blue Yonder has announced the acquisition of Optoro, a returns software platform, for an undisclosed price.
AND FINALLY …
Keychain Raises $30M in Series B Funding
Keychain, a manufacturing supply chain platform for the consumer packaged goods (CPG) sector, announced that it has raised $30 million in Series B funding and plans to enter new CPG verticals.
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Did you know that RMW Commerce has another podcast? Check out The Watson Weekend for an unfiltered and lively eCommerce chat each week with me, Rick Watson, my co-host Jess Lesesky, and an array of interesting guests and topics. All focused on eCommerce. You can find the Watson Weekend by searching for it on iTunes, Spotify, or Youtube.
That’s all for this week! Till next time Watsonians.....
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Hi, I’m Rick Watson, CEO and Founder of RMW Commerce Consulting and host of the Watson Weekly podcast - your essential eCommerce Digest.
To hear new episodes of the show every Monday morning, subscribe now at rmwcommerce.com/watsonweekly and wherever you get your podcasts.
