Retention is becoming a much bigger job.

It’s not just welcome flows, abandoned carts, and “send another campaign.” Brands are treating retention as a revenue system: one that shapes acquisition, improves repeat purchase, supports forecasting, and gives customers a real reason to stay engaged.

That’s what we covered at Commerce Roundtable’s Retention Roadshow.

We pulled together nine sessions from operators across email, SMS, lifecycle, AI, forecasting, and community-led growth, including Max Sturtevant, Fil Pejic, Devyn Pukteris, Rytis Lauris, Melanie Balke, Anwar Abdul Jawad, Daniel Guerra, Chris Lang, and yours truly Jimmy.

This morning, we're covering a quick guide to each session, plus links to watch the full talks.

Also inside:

→ Your winning email has a shelf life. Nobody told you when it expired.
→ Your first impression is too valuable to waste. Avoid these three mistakes in your welcome flow
→ The best part of Commerce Roundtable San Diego isn't on the agenda
→ Shoppers are ditching brand chatbots for ChatGPT, most companies using AI aren't seeing results, + back-to-school dollars are shifting fast

Your winning email has a shelf life. Nobody told you when it expired.

That layout crushed in April, so it became the template. And every send since, the numbers have slipped a little more. 

Spoiler: Your list isn't tired of email. They're tired of THAT email.

Paid media treats creative fatigue as a law of physics. 

The algorithm watches every combination, retires what's cooling off, and rotates in the next one, per person, automatically. Nobody schedules a meeting about it.

In email, a fading winner has to be noticed, rebuilt, and retested by hand. By the time anyone acts, it's been underperforming for months.

Allan gives email that reflex. 

Your team stocks the shelf with headlines, images, offers, and copy, and Allan builds the right version for every subscriber, getting sharper with every send.

Winners fade. The difference is whether something is ready to take their place.

→ Start your 30-day free trial 

*Sponsored

Commerce Roundtable’s Retention Roadshow: 9 Sessions to Help eCommerce Brands Build Smarter Email & SMS Programs

Retention isn’t just about sending more emails anymore. It’s about building a system that helps customers buy faster, come back sooner, spend more over time, and actually get value from the product they purchased.

We took the Retention Roadshow across the country to New York City, Austin, Miami, and Los Angeles to hear directly from the operators shaping the future of retention marketing.

Those conversations became the foundation of the Roadshow. Across nine sessions, operators shared the frameworks they're using today, from foundational email flows and AI-powered decision making to post-purchase experiences, retention forecasting, and community-led growth.

Below, you’ll find a quick guide to each session, plus links to watch the full talks.

The 2026 Email Flow Playbook: Pop-Ups, Welcome Series, Abandonment & Retention Flows

With Max Sturtevant, Founder of Well Copy

Max Sturtevant gets tactical on the email and SMS systems most brands should have dialed in before chasing advanced segmentation or overly complex journeys.

Rather than chasing increasingly complex automations, Max makes the case for getting the fundamentals right first. Strong pop-ups, high-converting welcome series, faster abandonment flows, and thoughtful post-purchase experiences generate far more impact than layering on dozens of low-volume niche automations.

Max also breaks down why pre-purchase flows need speed, why abandoned cart and checkout emails should put the product front and center, and why post-purchase should focus less on immediate upsells and more on helping customers actually use the product.

Retention Marketing Playbook: AI Testing, Pop-Ups, Offers & Creative to Win BFCM

With Fil Pejic, Founder of Bedford

Fil Pejic’s session is a reminder that the best retention teams don’t just copy what worked for another brand. They test for lift, profit, and actual business impact.

Fil walks through how brands should approach BFCM months before the rush, using AI to analyze tests, compare holdouts, and understand which pop-ups, offers, creative formats, and send strategies actually move the business forward. The point isn’t to test everything. It's to identify the handful of variables that can meaningfully change revenue, margins, and long-term customer value.

This session is especially useful for teams that know they should be testing more, but need a clearer way to prioritize what’s worth testing before peak season.

5 Hidden Patterns That Broke The Standard Industry Playbook on Retention Revenue

With Devyn Pukteris, Head of Lifecycle Marketing at Sweat Pants Agency

Devyn Pukteris challenges some of the standard rules marketers tend to follow around subject lines, creative, CTAs, and campaign structure.

One of the most interesting ideas from this session is that improving one metric can actually hurt another. A subject line that drives fewer opens might attract more qualified clicks. A simpler email might outperform a beautifully designed one. And a campaign focused on one clear action often beats one trying to accomplish five things at once.

Devyn makes the case for questioning assumptions and optimizing for revenue, not vanity metrics.

Connected AI for Email & Retention Marketing: Using MCP to Turn Data Into Actions Faster

With Rytis Lauris, Co-Founder & CEO of Omnisend

Rytis Lauris takes on one of the biggest problems in modern retention marketing: teams have more data than ever, but not enough time to turn that data into decisions.

In this session, Rytis explains the difference between generic AI and connected AI. Generic AI can help write copy, brainstorm win-back ideas, or summarize strategy. Connected AI, using tools like MCP, can access real marketing data, pull context from your systems, identify changes, suggest segments, and help marketers move from question to action faster.

It’s a practical look at how AI becomes more valuable when it’s connected to the systems marketers already use, instead of sitting outside the workflow.

The Anatomy of The Golden Goose: Stop Discount-Led Churn

With Melanie Balke, Founder of The Email Marketers

Melanie Balke’s session reframes retention around one of the most overlooked moments in the customer journey: what happens after someone buys.

Her argument is simple but important. A first purchase doesn’t mean the customer is retained. It means they gave you a chance. If brands acquire customers through aggressive discounts, fail to communicate the real value proposition, or don’t help customers reach the product’s “magic moment,” churn becomes much harder to fix later.

Melanie walks through how acquisition, post-purchase onboarding, first use, second purchase, subscription experience, win-back, and loyalty all connect. This session makes a compelling case that post-purchase is where retention is won or lost. Before asking customers to buy again, brands need to answer a simpler question: Have we helped them succeed with the first purchase yet?

From Retention Calendar to Revenue Plan: Forecasting, Pivots, and Hitting the Number in E-Commerce

With Anwar Abdul Jawad, Prophit Engineer at Common Thread Collective

Anwar Abdul Jawad brings a finance and operating lens to retention marketing, showing why a calendar of sends isn’t the same thing as a revenue plan.

The session breaks down how retention teams can forecast campaign and flow revenue, diagnose gaps, and pivot when performance misses the plan. Anwar explains why forecasting isn’t about perfectly guessing what will happen next month. It’s about setting a target, understanding how you expect to get there, and creating a clear reason to act when the numbers move off track.

For marketers who want retention to have a stronger seat at the revenue table, this session is a quick fire guide for tying email and SMS directly to margin, forecasting, cash flow, and business goals.

An AI System for Accurate Email & SMS Revenue Projections

With Daniel Guerra, Head of Data at New Standard Co

Daniel Guerra goes deep on one of the most underused disciplines in retention: projecting email and SMS revenue before the month starts.

Instead of pulling last month’s revenue, adding a growth target, and hoping the number lands, Daniel shows how teams can build a projection system around real inputs. That includes revenue per recipient, deliverability, segment health, SMS overlap, list growth, inventory, acquisition, seasonality, campaign plans, promo news, and recent flow changes.

His core point: The system works best when AI helps with the math and structure, while the operator decides what’s realistic, what changed, and what needs to happen next.

Retention Redefined: The 8 Steps to Profitable Email & SMS in 2026

With Jimmy Kim of Commerce Roundtable and eCom Email Marketer

Jimmy Kim lays out a broader framework for what profitable retention should look like in 2026.

This session moves beyond the idea that retention is just campaigns and flows. Jimmy breaks down the shift from “send more” to “send smarter,” showing how email and SMS should support the full customer journey: awareness, interest, first purchase, onboarding, second purchase, habit, emotional buy-in, and advocacy.

He also digs into segmentation, zero-party data, SMS strategy, and why personalization only works when you understand where the customer is in their journey.

How Fresh Chile Grew 1M Email Subscribers by Building a Community, Not Discounts

With Chris Lang from Fresh Chile Co and MOVE

Chris Lang closes the series with a different kind of retention lesson: the strongest email lists aren’t built on discounts alone. They’re built on access, trust, story, and community.

Chris shares how Fresh Chile grew to over 1 million email subscribers by giving people a reason to care and a reason to act now. Instead of asking people to “subscribe for updates,” Fresh Chile sells access: first pick of the harvest, limited seasonal drops, recipes, giveaways, education, and a real connection to the Hatch chile community.

Watch the Full Retention Roadshow Series

Each session brings a different angle, but together they point to the same bigger shift: retention marketing is becoming more operational, more measurable, and more central to profitable growth.

Explore the full Retention Roadshow sessions above and start building the retention program your next stage of growth actually needs.

👌 The quick take:

Your first impression is too valuable to waste… avoid these three mistakes in your welcome flow:

The best part of Commerce Roundtable San Diego isn't on the agenda.

Sure, the speakers always hit. But ask anyone who's been before and they'll tell you the same thing: it's the conversations between sessions, the ideas over lunch (and yes, the lunch itself), and the introductions that turn into partnerships.

Commerce Roundtable returns to San Diego September 21-22, bringing together 750+ founders, operators, marketers, and agencies for two days of tactical content and networking all on top of the San Diego bay.

Use code EEMVIP to save 40% on your ticket.

→ Grab your ticket

🍦 DTC Scoop:

Shoppers would rather ask ChatGPT than your chatbot

Customers are three times more likely to use third-party AI tools like ChatGPT or Claude than a brand's own chatbot when they need help shopping. And that gap is growing fast: third-party AI usage doubled in the past year while brand chatbot adoption has been flat since 2022. The big reason? Brand bots can answer questions but can't actually help you buy anything.

90% of companies say they're using AI (about 5% are seeing results)

There's a growing gap between AI adoption and AI actually doing something useful. A new report found that while nearly every company claims to be using AI, only 5 to 6 percent report any significant improvement from it. The takeaway isn't that AI doesn't work but that most companies rushed to adopt it without rethinking the operations around it.

Back-to-school spending is flat, but where the money goes is shifting

Deloitte says families will spend about $557 per student this year, which looks steady until you factor in inflation (it's actually down 6%). The real shift is actually behavioral; kids are filling their own carts now (61% of them), almost a quarter of families are shopping through social and influencer recs, and clothing is winning while tech spending cratered 16%.

Meta built an AI tool that puts your products in shoppers' living rooms

Meta's new Muse Image feature lets shoppers upload a photo of their actual room and see how a brand's products would look in it. It pulls directly from a brand's existing ad catalog, so there's no extra setup required.

Annnnd that’s a wrap for this edition! 

Thanks for hanging with Chase and me. Always a pleasure to have you here.

If you found this newsletter helpful (or even just a little fun), don’t keep it to yourself! Share ecomemailmarketer.com with your favorite DTC marketer. Let’s get them on board so they don’t miss next week’s drops.

Remember: Do shit you love.

🤘 Jimmy Kim & Chase Dimond

PS - Your next best customer might be reading this right now. Want in? Email Jimmy to sponsor this newsletter and more.

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