The Art Of Boring
I am certain you are overcomplicating retention
Hi team,
Between the four emails a day from Wayfair, the third SMS this week about a sale I had already seen, and a push notification that appeared six hours after I had already bought the item, it’s hard not to notice how poorly coordinated retention has become.
None of this feels especially thoughtful. It mostly feels like systems talking past each other.
Somewhere along the way, retention turned into a damn performance. More messages, more schedules, and more systems layered on top of each other in the name of staying “top of mind,” without much interrogation of whether all this activity actually beats a quieter approach where systems respond to what customers are doing, rather than what a calendar says they should be doing.
The brands that seem most in control right now are rarely the ones doing the most. They are usually running simpler programs that hold up without constant babysitting, even when someone goes on vacation or priorities shift.
This week: how retention got this complicated, what campaign-heavy systems really cost, and why the most valuable thing you can build right now is boring enough that you forget it’s there.
This week’s newsie is brought to you by Tapcart AI, which matters less as an “AI launch” and more for what it signals about where retention is heading.
For the last decade, retention tools have mostly pushed teams toward more. More campaigns to plan, more segments to maintain, more calendars to manage, and more decisions to revisit every time performance shifts. That approach can work, but it depends heavily on constant human involvement to keep everything running smoothly.
Tapcart is leaning into a different direction with how they think about mobile retention. The emphasis is on reducing how much manual effort it takes to keep an app performing as a retention channel. Execution that responds to customer behavior automatically. App experiences that don’t need constant weekly manual upkeep. The kind of infrastructure that just runs without you having to think about it.
That’s what “self-driving” actually means in practice. Not replacing the team. Removing the repetitive work that eats time without moving the needle.
What Tapcart AI looks like:
Campaigns that trigger based on behavior, not calendar dates you have to set every week
Personalization that adjusts to customer patterns without manual segmentation
App performance that improves over time without constant tweaks
If you want to see how Tapcart is thinking about this shift, you can explore Tapcart AI here:
How We Got Here
Ten years ago, retention was mostly email. Welcome series, win-back campaigns, and promotional sends tied to sales. The stack was small because the options were limited, and you could understand the whole system without needing a diagram.
Then the channels multiplied. SMS became standard. Push became accessible. In-app messaging showed up. Loyalty grew into its own operational lane. Personalization tools promised to make everything smarter and came with long onboarding cycles and ongoing maintenance that nobody mentioned in the demo.
Each addition was reasonable on its own, and for a while, the promise held.
I started noticing the cracks about two years ago while helping a home goods brand audit their retention setup. We found fourteen separate automations spread across four platforms. Half of them had been built by people no longer at the company. One flow had been running for eighteen months, and nobody could say with confidence whether it still made sense. Nobody wanted to turn it off in case it was load-bearing.
The channels still work. Managing them has become its own job. Retention teams went from running campaigns to managing infrastructure, and a lot of strategic time got absorbed by coordination and QA.
Here’s how it compounds.
Someone adds cart abandonment because it performs. Someone layers in browse abandonment because customers are dropping earlier than expected. Someone builds a post-purchase sequence to drive repeat orders. Each decision makes sense in isolation.
These systems never stay isolated. They run in parallel, with different triggers, timing rules, owners, and assumptions. A customer abandons a cart at 2pm. Your email flow fires immediately. Your SMS goes out at 4pm because that’s when batch sends were scheduled. Your push arrives at 6pm because the timing was set months ago and hasn’t been revisited.
None of these systems know what the others are doing. The customer just knows they got hit three times in four hours about the same cart and is now slightly less inclined to come back.
The Real Cost of Always-On Management
The obvious cost of a complex retention stack is time. Someone has to build flows, monitor dashboards, adjust timing, update creative, manage deliverability, and troubleshoot edge cases.
The less obvious cost is fragility.
A fashion brand I know had their entire retention program effectively held together by one person who had been there for three years. She knew which flows couldn’t be edited without breaking downstream triggers, why the win-back series had a random 36-hour delay, and which fields could not be touched without breaking a loyalty sync.
When she left, that knowledge left with her. The team inherited a Jenga tower of automations that nobody wanted to touch.
Change becomes expensive, so teams default to keeping things running. They tweak around the edges, but the underlying system stays the same because the risk of touching it feels higher than the upside of improving it.
A beverage brand described their retention program as “25% strategy, 75% not breaking what already works.” That ratio should be inverted.
The Quiet Shift Already Happening
I’ve been watching this shift over the last year in conversations with retention leaders who have started simplifying their stacks.
A DTC apparel brand cut push from twelve scheduled sends a month down to three. Everything else became event-driven, responding to browsing behavior and purchase patterns in real time. Push open rates went up 31%, and nobody on the team thinks about scheduling anymore.
A supplements company deleted their browse abandonment flow entirely. It was generating a tiny fraction of retention revenue and driving most of their unsubscribe volume. Performance held and complaints dropped.
A home goods brand told me their goal for 2026 is “systems we can ignore,” meaning infrastructure reliable enough that the team can focus on strategy instead of maintenance.
The pattern is consistent. Teams are moving away from campaign volume as a success metric and toward resilience as the standard. Fewer scheduled sends and more emphasis on systems that can run without constant attention.
Performance stays flat or improves.
Teams aren’t getting bigger, budgets aren’t expanding, and expectations keep rising.
What Good Looks Like
I spoke to someone last week who described their retention program as “me-proof,” meaning it was clearly documented and built simply enough that someone new could take it over without having to reverse-engineer years of decisions.
That should be the standard.
Every tool you add increases surface area for failure. Another login, 10 more integrations, another dependency that can break at the wrong time. The best retention setups in 2026 won’t be the most sophisticated. They’ll be the ones you can explain in five minutes to someone who just joined.
That also means prioritizing owned channels that compound over time, rather than paid re-engagement that resets every month.
Where Humans Still Matter
Even in a boring retention model, strategy still matters.
Humans decide what the experience should feel like, what trade-offs to make between frequency and relevance, and which behaviors actually deserve a response. Systems can execute rules reliably, but the rules still need judgment behind them.
Scheduling sends is not a great use of human time. Deciding whether your brand should feel calm or urgent is.
The goal is to spend less time maintaining execution and more time shaping the experience.
Why Boring Wins
The best retention programs are the ones you barely think about because they run consistently and free up time for work that actually moves the business forward.
I keep coming back to a retention director who told me their biggest win last year was not launching anything new. What they did instead was make the system more durable. Their retention became boring in the best possible way.
If your stack still feels like it requires full-time babysitting, it’s worth asking what would need to change for it to become quieter. Not because quiet is virtuous in itself, but because systems that operate without constant attention give teams room to do better work.
Boring retention is better retention. And in 2026, that’s the only model that scales.
That’s it for this week!
Any topics you’d like to see me cover in the future?
Just shoot me a DM or an email!
Cheers,
Eli 💛
P.S. If you want to figure out how to get your brand to rank high in LLMs and show up in ChatGPT, Gemini, and more… check this out.
You write really well! In a world where the common advice is to 'add', it's refreshing to read this POV. I can't stand cart abadonment whatsapp messages - makes me never want to buy from the brands. And like you said, it's often terribly uncoordinated.