At some point in the last four years, the average eCommerce operator's software stack quietly became a form of emotional coping masquerading as infrastructure.
It began with a sensible decision. A tool was needed. The tool was acquired. It had an integration. The integration suggested a complementary tool. That tool had an annual plan at a discount if you committed before Friday, which you did, because it was Thursday and someone had just left a difficult comment in a Slack thread and the quarter was not going well and frankly the demo had been quite good.
This continued for longer than anyone intended.
There are now, depending on the brand, between fourteen and thirty-one tools involved in running a mid-sized DTC operation. Several are solving the same problem with the quiet competitive dignity of colleagues who have never been introduced. One was implemented by an agency that is no longer retained, for a strategy that is no longer active, and is currently sending a weekly report to an inbox that forwards to another inbox that nobody has opened since the rebrand.
The stack has a loyalty program that has demonstrated, across four years of operation, considerably more loyalty to its own billing cycle than to any customer who has ever redeemed a point. It remains, because cancelling it requires a conversation, and the conversation requires a meeting, and the meeting requires someone to own the agenda, and that person is already in three other meetings about something that was urgent in February.
Somewhere in the stack is a tool that sends a particular type of notification that one particular person found useful in 2022. That person left. The notification continues, faithfully, into the void, like a lighthouse keeper who was never informed the ships stopped coming. Every four hours. Into the dark. Professionally.
None of this is anyone's fault specifically. It is the natural geology of a scaling eCommerce brand: layer upon layer of good intentions, quarterly panic purchases, and software that has long since outlived the problem it was hired to solve, now simply coexisting in a Shopify ecosystem with the quiet resignation of people who have all been assigned to the same project and are no longer certain what the project is.
The invoices, at least, arrive on time. Someone set that up correctly.
Upcoming Events
Most retention events are a day-long sequence of slides, sponsored lunches, and tactical frameworks that were useful to someone, somewhere, under conditions that no longer apply to your business.
The Retention Roadshow is making a reasonable case for being different. One day. A deliberately small room of a mere 75-100 growth and scale-stage DTC operators.
Four cities in June — New York, Miami, Los Angeles, Austin — and an agenda built around lifecycle marketing and LTV rather than ninety minutes of attribution discourse and a founder panel where everyone agrees that brand matters.
Tweet of the Week
He Went From $0 to $100M in 11 Months — And You're Still "Planning"
AI agents are now shopping on behalf of your customers with the quiet confidence of someone who has already read your entire website, noted the inconsistencies, and decided to recommend a competitor with better catalog hygiene.
They know the customer's dog. The breed. The bag size. What they do not know.. because you have not told them in any legible, structured, or internally consistent way… is what your subscription offer actually is, what it costs, what it changes, and whether it is called "Auto Ship" on the product page or "Subscribe and Save" on the explainer page you may or may not have built before pivoting to a loyalty program in Q3.
Matt Holman and David Bradley sat down to discuss what agentic commerce requires from a subscription brand before the machines make their recommendations without your consultation.
The conversation covers, in such coherent fashion that it borders on the unhinged:
structured data
explainer page architecture
the precise and underappreciated art of telling an AI what your product is not for
why Chewy is currently eating everyone's lunch with the aggressive organizational enthusiasm of a brand that once decided its catalog should make sense
The data flip at the center of this piece is worth the price of admission alone: for years, your job was to capture customer intent. In agentic commerce, the agent already has the intent. Your job now is to give it something coherent to work with.
Most brands are not doing this. Most brands have a product page that was last audited during a rebrand, an explainer page nobody can find, and a URL structure that communicates the organizational confidence of a shared Google Drive folder named "FINAL v3 USE THIS ONE."
This is not a technical overhaul. It is a small, boring, commercially meaningful act of legibility that the majority of your competitors have not yet performed.
Do it before they do. Read the piece.
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Quick Shots
@zachmstuck When are we going to have Enhanced Games for eCom?
@MattOrlic “We hired a creative team, produced our best ads ever, but every single one flopped.”
Peter Quadrel PROPAGANDA IM PUSHING:
@wearetheselect "We're a premium brand. We don't do promotions."
Sarah Levinger “I don’t know why my customer buys.” 🫣
Here for the Memes
Top Headlines this Week
Best from LinkedIn
Not sure how I feel about this one . . . bummed a bit I guess.
Everlane spent a decade selling "radical transparency" and last week it was acquired by the company most often used as a synonym for the opposite.
The deal: $100M. Buyer: Shein. Seller: L Catterton, Everlane's majority owner.
This is the counter-point exit to what Chad Janis pulled off with Grüns . . . not a strategic buyer paying a premium for a brand that "resonates." Instead, a sponsor offloading to a fast-fashion competitor at a price designed to clear the debt and zero the common stock.
Look at where the $100M actually went. $25M to Gordon Brothers. $65M to the asset-based revolver. That's $90M of the headline number paid to lenders before a single shareholder saw a wire. The cap table below the preferred stack got rounded to zero in the polite, paperwork way.
This isn't an Everlane story. Allbirds did the same thing earlier this year at a smaller number. Honest Co. wound down DTC last quarter.
Two unglamorous things worth doing today:
Recommended SAAS & Services
Still on Klaviyo? This one’s for the Omnisend-curious.
Omnisend’s new on-demand webinar goes live June 15, walking DTC brands through how it stacks up against Klaviyo… and what it actually takes to migrate. Deniz, Omnisend’s Senior Onboarding & Migrations Manager, covers feature differences, pricing, SMS, support, common pain points, and the step-by-step migration process, from lists and segments to automations, deliverability, and onboarding support. [Watch from June 15]Scaling paid media shouldn’t feel like gambling. Sum Digital helps 7–9-figure ecommerce brands turn ad spend into predictable, profitable growth across Meta, Google, and TikTok—without bloated teams or black-box reporting. Senior operators only, creative that actually converts, and a relentless focus on ROAS. If you’re done paying for spend instead of results, Sum Digital is your agency of record.
Stuck between an overpaid $80K/Year US hire and an inexperienced $5/Hour VA? Tidal helps you hire experienced, execution talent globally that outperforms US hires, at a fraction of the cost. Built by operators focused on hiring better talent, not just cheaper talent. Get started with a free payroll audit today --> www.hiretidal.com
Stat Attack
Software stacks, like sediment and certain agency relationships, do not resolve. They accumulate. The sensible tool becomes the legacy tool becomes the thing nobody touches because the last person who understood it left a note that was not entirely legible and is now, itself, a kind of institutional knowledge.
This is simply how it goes. The invoices will continue. The notification will fire into the void on schedule. And somewhere, a loyalty program will renew with the quiet confidence of something that has never once been asked to justify itself. ✌
And with that, we bid you farewell!
👆👆👆
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