Is it Time to Migrate Your Email & SMS?

Hey everyone,

Welcome back for another bite to chew on.

Retention in DTC has become a confusing mess. Most brands hire a retention person, hand them Klaviyo, and call it strategy. The metrics they chase (LTV, repeat rate) drop six months after the actual problem started, and nobody quite knows what to do about it. Most brands treat email and SMS like the engine of retention. They're really just the dashboard.

Eli Weiss has spent the last several years inside brands at exactly that inflection point. He led customer experience at Olipop when it was a 14-person company nobody had heard of. He brought retention and CX under one umbrella at Jones Road Beauty. He's now VP of Advocacy at Yotpo, where his title (in his own words) "changes every quarter" depending on what the customer needs. The DTC Twitter loud-take version of him does not really exist.

What came out of an hour of conversation was less a list of email tactics and more an operating philosophy. Retention is a byproduct of every decision a company makes. Email and SMS are the smallest piece of that picture, just the most measurable. And the brands that compound are the ones treating customers like real people instead of cohorts, then writing copy that reads like a founder actually wrote it.

On the Menu:

BTW, this is just a taste of our chat with Eli. Listen to the full recording here.

Most brands don't switch email platforms because they spotted a flashy new feature. They switch because they're paying a premium for service they're no longer getting.

That gap (the unresponsive CSM, the strategic guidance that disappeared, the bill that keeps climbing while the value flatlines) is the real reason brands move, not a missing report or a prettier UI. Omnisend built their migration team around exactly that pattern.

If you're stuck on another platform, Omnisend's migration team moves you in 5 days, free. Contacts, automations, templates, segments: their team rebuilds the whole setup for you. In less than a week you could be saving up to 35% on what you're paying today.

Click here to move to Omnisend FREE in 5 days!

Eli's most pointed critique of how brands approach retention: they treat it like a math problem. If you can fix repeat rate, you can fix LTV. If you can fix LTV, you can fix the business. But repeat rate dropping today means the customer was lost six months ago.

As Eli put it: "by the time that number drops, you lost the customer six months ago and now you're trying to clean it up with sending more emails."

The thing that actually moves repeat rate isn't a better welcome flow. It's whether the product was what you promised, whether the shipping was what you promised, whether the brand was what you said it was. The retention manager clicking buttons in Klaviyo is solving for symptoms, not causes. Email and SMS are the smallest piece of retention, just the most measurable. Most brands have that ratio inverted.

Eli's second move is to question the entire premise of the retention hire. Most brands look for "the best email person" and assume that person exists in the abstract. But being great at retention at Olipop doesn't transfer to a skincare brand. Being great at email for Magic Spoon doesn't transfer to a sloppy dropship operation.

The reason is contextual. Retention depends on the customer, the product, the price point, the category, and the brand promise. "Being great at retention at one brand in one industry means nothing," Eli said.

His own version of that work at Jones Road, in his sixth week, was 30 customer calls. Cody Plofker pushed him to do it. He went from knowing nothing about mascara to (his words) "a menace" about it. That foundation is what most brand hires skip, and it's the thing that separates someone who can actually move the business from someone who's just clicking through best-practice templates.

When asked what brands can do tomorrow that doesn't involve email or SMS, Eli's answer was concrete:

The brand he highlighted in the episode ran a version of this on a thousand customers and got 300 community opt-ins on the first send. Those 300 became the response panel for every survey, every product call, every roadmap question. The work didn't scale. That was the point.

The other 99.9% of brands, in Eli's framing, never try. They assume customers won't respond. The few that do respond end up running better businesses than the ones that don't.

What you can do: Pull a list of customers who bought once and never came back, then email a slice personally from a founder address asking why. Treat the answers as roadmap input, not customer service tickets.

Eli has spent the last year and a half on both sides of the migration equation: first pushing brands toward Yotpo, then pushing them toward Omnisend through the partnership. His view from inside the SaaS side is direct. The feature comparison is almost never the real reason.

"It's very rarely like a feature gap," he said. The actual reason brands move is structural: the CSM stopped responding, the strategic guidance disappeared, the pricing stopped making sense relative to the value being delivered. The flashy new UI is a tiebreaker, not a trigger.

He took it further. In 6 to 12 months, every platform will be shipping hundreds of features per quarter. The alpha is no longer in the feature count. It's in which two or three features matter for your specific brand, and which partner will actually help you use them well.

Eli's most useful migration advice came in two parts. The easy part: most partners will handle the migration for you. Suppression lists, deliverability, automations, screenshots of SMS flows that get rebuilt with three clicks. On the SMS side specifically, he pointed out that everyone is using the same toll-free numbers and the same Twilio piping. The technical lift is far smaller than the fear around it suggests.

The hard part is timing and discipline. Don't migrate in the middle of Q4. Don't migrate in the middle of a launch. June, July, and into August for BFCM-ready brands is the right window because the stakes during the transition are lowest. Keep your suppression lists, understand your deliverability metrics, and pick a partner with strong support and a clear handoff plan.

In Eli's words: "this is not rocket science."

Not every tool in your stack needs an annual review. The back-in-stock app probably doesn't. The pop-up vendor probably doesn't. But email and SMS together drive 25 to 30% of revenue for most DTC brands, which means they deserve a regular look.

Eli's two triggers for evaluation: you feel like you're missing something (usually a service or guidance gap), or your costs are climbing without a clear return. Both are signals that the value side of the equation has shifted, and neither has anything to do with a competitor's feature release.

His broader frame: "build for the long run and don't be an idiot." Profitability matters now in a way it didn't three years ago. The tools that survive are the ones that align price with actual value, and that's worth checking on the channels that move the most revenue.

What you can do: Once a year, audit the two highest-revenue tools in your stack. If service has slipped or pricing has crept up without new value, it's time to evaluate alternatives.

Eli credited Cody Plofker at Jones Road with the framework that became foundational to how he builds flows. At each stage of the customer journey, the objection is different, and the email or SMS has to answer that specific objection.

A welcome flow subscriber gave you their email but not their credit card. The objections are predictable: I'm not sure this product will solve my problem, I'm not sure it's worth the price, and there might be a better competitor I should look at first. The flow has to remove those three in order, not list product features.

A post-purchase customer has already given you their credit card. The job there is the opposite: thank them, set them up for success, and cross-sell with intent. Eli's framing: you're a business, not an organization, so cross-sell, but do it thoughtfully.

An unengaged customer is a third problem entirely. Different journey, different objection, different message. Most brands send the same generic blast to all three. That's why most brands' retention engines underperform.

On the campaign side, Eli's recommendation was structural. Stop building campaigns by coming up with a Slack idea on Tuesday and sending it Wednesday. Pick three core brand pillars (community, education, and a third that fits your category) and route every campaign through one or two of those pillars.

A community email can still have a CTA that sells. An education email can still have a community component. The pillars aren't silos, they're filters. The point is to give each email a reason to exist beyond filling the calendar.

The brands that skip this step end up with what Eli described as the agency default: the entire best-practice book thrown at flows and campaigns, design language that looks like everyone else's, and copy with no unique point of view. The fix isn't a redesign. It's deciding what you actually stand for and writing from there.

Eli's hottest take on the connected stack: the goal of consolidation was never one dashboard. It was a connected data layer that lets the brand treat one customer like one customer.

A one-star review should change how you email that customer. A loyalty member about to lapse should get a different post-purchase message than a first-time buyer. A subscription customer who keeps requesting flavor swaps is telling you something about your roadmap. None of that is possible if the reviews tool and the email tool don't share context. The future of retention, in Eli's words, is one to one, not one to many.

One tactic he hasn't seen die yet: the plain-text email from the founder. "I'm still a sucker for a good plain text email," he said. The reason it still works is that it's the one format that hasn't been gimmicked into the ground. Most brands have abandoned it for designed templates. The brands that haven't are quietly winning the inbox.

What you can do: Tomorrow morning, open your welcome flow and audit it top to bottom. Remove the dead products, the outdated story, and the old logo: this is your brand's front door, and most brands have let it go filthy.