September 8th, 2025: Shopify Betting Big on Design, Amazon Still Stuck Muddling Through Day 2, Why Software Sales Is Still Hard in 2025, A New Podcast where SaaS Meets AI: Oh Shift
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It’s September 8, 2025 and this is the Watson Weekly - your essential eCommerce Digest!
Today on our show:
Shopify Betting Big on Design
Amazon Still Stuck Muddling Through Day 2
Why Software Sales Is Still Hard in 2025
A New Podcast where SaaS Meets AI: Oh Shift
- 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….
Shopify Betting Big on Design as Once and Future King in the Age of AI
Tobi has in the past called himself a "design superfan". It's reflected in the growth of Shopify, and I think is underappreciated in the company's history.
There has been recent news with Shopify in design, but it wasn't the first. Actually, for that you must go back to 2013. Shopify acquired Jet Cooper, a UX design studio, which brought Satish Kanwar to Shopify.
Interestingly, Shopify used to have a Head of Design, a co-founder Daniel Weinand who ended his time there around 2017.
Fast-forward when Shopify exited Logistics in 2023, it was clear where the puck was moving. Shopify was preparing to shed anything that would distract it from its core. You might say that 2024 was the year Shopify hit overdrive in its AI investment.
Kevin Scott added to the Board, and a new AI-focused CTO. The launch of Sidekick.
In 2025, what is happening in Shopify's world? Design is Colliding with AI.
Just in 2025:
* Horizons launched, which allows AI-generated sections
* A complete AI storefront builder was announced
* Sidekick gained new capabilities, such as designing promotions and banners
* Carl Rivera, formerly head of Shop App, former founder of Tictail. Now Chief Design Officer. Carl's promotion ended an 8 year spell at Shopify without a head of design.
Carl was previously responsible for Shop App and Shop Pay.
* Shopify Design Studio was just (re-?) born last week from the acquisition of Molly Design Studio.
So where is the puck moving? Of course it's anyone's guess.
But creating companies that differentiate on design in the age of AI seems to be the bet. A new C-level role.
Keep in mind, this is from a company that has zero Chief Marketing Officer, and has not since 2020. But now they have a Chief Design Officer (again).
Priorities.
While you may or may not agree with the bet Shopify is making, it's important for the ecosystem to recognize, a tremendous bet has in fact been made inside of Shopify. A bet I believe to be equal to its focus on AI, and equal to its previous focus on Logistics. (In focus not capital!)
And that bet is on the primacy of Design as a competitive, sustainable differentiator in the age of AI. Frankly, I think the bet is simple.
Experiences need taste, and Shopify aims to provide it, along with all the tooling that merchants and agencies need to succeed and differentiate in the age of AI.
If AI becomes an uber-designer on its own, it might be a dumb bet. But, that's why it's a bet, right?
Still this is not a bet which feels risky to Shopify. It feels instead - comfortable. Almost like something they’ve bet on before that seems to have turned out pretty well for them.
>> closer
[References:]
https://www.linkedin.com/posts/ecommercestrategyconsulting_shopify-betting-big-on-design-as-once-and-activity-7368609905852698626-iFoZ
Our Second Story
Amazon Still Stuck Muddling Through Day 2: Now What?
On the heels of a reportedly slower Prime signup from the last Prime Day, Amazon is trying to figure out how to borrow from Netflix and other players to trim some account-sharing of Prime free-shipping with non-household members.
Some outlets called this a "great benefit". tbh I didn't even know this was a benefit. But on the heels of recent reports of a slower amount of Prime signups during Prime Day, it's a bad look.
I expect part of the thesis of slower Prime signups is that wealthier households are starting to become saturated, and those that were sharing the benefits with their kids are now just going to have to pony up more formally. Sounds like a tweak more than anything.
Not going to solve the fundamental problem facing Amazon: a seemingly endless acceleration of Day 2 Thinking.
There are numerous reports out there Amazon is trying to return to its "hardcore" culture. Laughable. The reality is, once the genie is out of the bottle it simply does not get put back in.
In other words, a non-founder like Jassy trying to execute "founder-mode" priorities at Amazon's size comes off like another warmed-over three-letter-acronym revamp.
We want leaders who act like owners! Yet... these owners also need to:
* monitor their phone usage.
* itemize their meals reimbursements.
* RTO where we want you to
Doesn't sound like ownership to me, smells like serfdom.
Truth is, Amazon had a famously frugal culture that employees complained about but they knew the drill. Jeff still had the door desk, right? Who am I to complain.
Long past this. Yes these are the days that Jeff warned us all about.
One investor even mused that Jeff might need to come back to rein in things. The reality is, even if Jeff came back, founder mode would not return. Why
Simple.
"127 meter Yacht" Jeff is not the same as "Door-desk" Jeff.
My advice would be stop talking so much about the bureaucracy, start delivering more for the customer. Amazon has a ton of great qualities, fantastic people, and outstanding service. Your people are not the enemy -- they are your greatest enablers. If your supposed fantastic leadership (of which Jassy was a leader most of this time) was so great, why are there so many bad people?
I hope just hope Amazon doesn't get lost in a corporate quagmire of self-doubt.
>> closer
[References:]
Our Third Story
Why Software Sales is Still So Hard in 2025
Most new sales leaders and co-founders think things are pretty simple:
Step 1: Spam enough people to get a meeting with someone who will listen.
Step 2: Feature vomit all the things.
Step 3: (a miracle happens)
Step 4: Revenue!
And to that, I have one question for you: "Are you smarter than Steve Jobs?"
He famously hated Enterprise sales. Why? Just listen:
"What I love about the consumer market, that I always hated about the enterprise market, is that we come up with a product, we try to tell everybody about it, and every person votes for themselves. They go 'yes' or 'no,' and if enough of them say 'yes,' we get to come to work tomorrow. That's how it works. It's really simple. With the enterprise market, it's not so simple. The people that use the products don't decide for themselves, and the people that make those decisions sometimes are confused."
Simply, the user is not the economic buyer. And the economic buyer has other motivations. This simple insight captures the bulk of problems in most software companies today.
"What we have here is a failure to communicate. Some men, you just can't reach." -- Cool Hand Luke
I have a feeling Steve Jobs was a big fan of the Captain in the movie. I can't tell you how long it's taken me to learn and incorporate simple insights like this.
If you have ever found yourself thinking after a demo:
"They surely will go with us, they have so many problems!"
You actually have no idea what business you are in. You are not in the business of solving problems. Any business has thousands of problems, most of which a buyer will never tell you about.
Instead, you are in the business of creating trust. Yes, even in the age of AI this is still true.
[References:]
[PAUSE]
And Our Last Story
A New Podcast Where SaaS Meets AI: Oh Shift
In case you missed it, last week I launched a brand new podcast, you can find it on the RMW Commerce Youtube Channel.
Oh Shift is a podcast at the collision between AI and the typical way we have run Software as a service providers for the last 25 years. How are you changing how your company operates? Is it different for each department? How do you lead through the change?
Take a listen to quick preview of me with John Shao, CTO and Co-Founder of Order Management company Pipe17.
Play 3 minute clip.
<insert 3 minute clip>
[References:]
It’s That Time Friends, for our Investor Minute. We have 5 items on the menu today.
First
Bonsai Secures $1.8M Investment for First-Party Marketing Intelligence Platform
Bonsai, a first-party marketing intelligence platform, announced that it has raised $1.8 million in funding, which will be invested in product development and go-to-market initiatives.
Second
Flexport Sells Convoy's Technology to DAT
Flexport announced that it has sold Convoy's technology platform to DAT, a business unit of publicly traded Roper Technology, for a reported price of nearly $250 million after acquiring it for a reported $16 million.
Third
Global-e Acquires ReturnGO to Enhance Post-Purchase Experiences
Cross-border e-commerce platform Global-e announced that it has acquired ReturnGO to enable merchants to offer enhanced post-purchase experiences through easier returns and exchanges. The acquisition price was undisclosed.
Fourth
BigCommerce Acquires Domain Name Commerce.com for $2.4 Million
When BigCommerce announced its earnings at the end of July, the company also disclosed that it had spent $2.4 million on the domain name commerce.com. The company has a parent now, Commerce, that contains BigCommerce, Feedonomics, and MakeSwift.
Link: https://domainnamewire.com/2025/05/09/bigcommerce-buys-domain-name-for-2-4-million/
AND FINALLY …
Figma Starts Trading on NYSE After IPO
Design software company, Figma raised $1.22 billion from its initial public offering. It is now a publicly traded company on the New York Stock Exchange with the ticker Fig.
Link: https://www.cnbc.com/2025/07/31/figma-fig-starts-trading-on-nyse-after-ipo.html
[PAUSE]
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.....
[PAUSE]
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.
