The headless cycle: why brands went there, and why some are coming back

Headless ecommerce had a real moment, there.

For a few years, it was the answer any ambitious brand was supposed to give when asked about their tech stack. Speed, flexibility, creative liberation, enterprise credibility: the pitch was compelling. For some merchants, it delivered. For others, it created costs, complexity, and operational risk they weren't prepared for.

We sat down with the Chief Revenue Officer for iamota, Richard "Stitch" Sandor. Sandor is a 10-year veteran of the agency, and talks us through the full arc of the headless cycle. iamota is a boutique, premier-tier Shopify Plus agency based in Canada with deep expertise in subscription brand migrations.

Sandor has been in the room for both the early headless pitches and the re-evaluation conversations happening right now. His take is consistent throughout: the decision was never really about headless or headed. It was always about requirements. Shopify's evolution since 2021 has closed most of the capability gaps that originally drove brands toward headless. For the majority of merchants, a modern headed setup now gives them everything they need, and none of the overhead they were never built to carry.

iamota helps brands like Onnit and Dollar Shave Club migrate to Shopify Plus and get the most out of their online stores.

What kinds of brands is iamota working with today?

Sandor: We're a boutique, remote-first organization based across Canada with about 25 folks on the team. Shopify designates us as a premier tier agency partner. We focus on a few different areas.

One is migrating merchants to Shopify, and with specificity there we really focus in on subscription brands. We've got a lot of chops in subscriptions and health and wellness brands. We've worked with the likes of Dollar Shave Club, Vega, ONNIT, Balance of Nature, as well as with the Harry's group, now called Mammoth Brands. We've helped over 60 brands on Shopify, about 30 of those with migrations.

When did you first see brands seriously explore headless, and what were they trying to solve?

Sandor: In the early days there were murmurings of headless, like 2018, 2019. Shopify back then was nowhere near what it is today.

One early driver was international. Shopify didn't have a clean path if a merchant was selling in Canada, the US, Mexico, and different markets in Europe. Headless was a play there. From there it picked up momentum.

There were brands that wanted creative liberation: Shopify themes were seen as constraining, and some wanted a blank canvas. Performance was a key driver, too. Everyone was trying to get their site to load faster, tied to SEO and conversion. Developer freedom mattered: not being confined to Liquid meant teams could work in React and other frameworks.

Headless was also a way for Shopify to position themselves in enterprise while staying true to their grassroots roots. They even launched Hydrogen in 2021 which was a React-based framework designed for building headless..

“Brands were going headless before even looking at requirements. Our question was always: well, why? What are you trying to solve.”

Which of those original promises have held up, and which haven't?

Sandor: It really depends on the requirements of the merchant. In terms of international, that's no longer an issue. Shopify Markets made big headway there, so there are better ways to solve for that now than through headless. 

We can talk some about the innovation of Shopify because they've enabled more freedom within their core framework. You're able to do more on headed.

So it's not that headless can't do things anymore, it can, but the headed option has really progressed and evolved, knocking down some of those drivers to headless that are less relevant today.

You mentioned that headless got pushed toward merchants it wasn't right for. Can you walk through what that looked like?

Sandor: Headless was very applicable for some merchants, but it got pushed downstream. It was very appropriate for merchants with big GMVs, true enterprise-type merchants, but we were seeing merchants as low as $5 million GMV going: we need to go headless.

There was a situation in 2020 where we're pitching for a project and there were five agencies. We were the only one, upon looking at requirements, that said: "Actually, you know what? You can go headed. You're going to be totally fine."

After we had won it, we found out all the other agencies were pitching headless to this merchant. And it totally wasn't appropriate. They didn't have the GMV. They didn't have the technical team and the chops in house. They didn't have the budget. One, to stand it up and to go live, or the budget to keep it operating. Before even looking at requirements, brands were going: oh yeah we’re going to go headless. We were like well, why? What are you what are you trying to solve?

There was a lot of hype and momentum behind it, and people were getting ahead of themselves in some instances.

Once brands were live on headless, what issues came up most often?

Sandor: There were definitely challenges in operating a headless setup, particularly if you're a smaller merchant. The total cost of ownership and operating budget take a hit. It might be fast, but you either need a team in-house or you're really depending on an agency to support you with the tech stack.

There's one merchant that we're working with right now who is reevaluating their business. They're in a high-risk situation because they have the tech resources in house, but there are such specialized resources to hire someone. They've got two technical resources supporting headless and so there's a business risk. A couple of those resources leave or even one leaves, and they've got to rehire. There's a real challenge and tight talent pool to bring in a technical resource to fill that gap. And that was even more than the cost challenge actually. It was more a business risk in terms of resources that could support headless.

“Whether it's Rebuy or other apps, they're going to be easier to test, learn, and try in a headed environment. It's a big unlock for a lot of brands.”

What has Shopify added or improved since that initial headless wave that changes the decision today?

Sandor: Shopify has changed a ton over five years. Online Store 2.0 was a big unlock: sections everywhere, theme app extensions, app blocks. You can add UI in a modular and safe way without touching theme code. Meta objects gave merchants the ability to create custom data types and reuse them across the store, which addressed some of what headless CMSs were being used for. Shopify Markets solved international. Checkout extensibility was another big unlock. Shopify Functions gave brands meaningful backend customization. That's massive progress.

And it's not just Shopify. The apps have progressed too. Rebuy is a very different product than it was in 2021. The combination of Shopify and apps like Rebuy coming together and offering more customizable solutions is what really changes the equation.

Richard 'Stitch' Sandor of iamota dives deep into the headless-versus-headed architecture debate.

What's one signal that a brand should be re-evaluating its headless setup?

Sandor: A few things. Start with: why did you go headless in the first place? Note those original drivers, and then see if they're still applicable today. Shopify pushes out about 150 enhancements every six months. A lot of those original reasons may be solved. Then document your current state requirements, and your known future state requirements, so you're not just constraining yourself to today.

There are some limits in terms of ability to move quickly; to test, update, to iterate, to enhance. Because it is a more complex environment. If there's a desire to move a little quicker and you feel the current state on headless is holding you back, that's something to think about.

We're seeing more pressure on merchant teams as well. So team size is  shrinking a little bit on the merchant side. Everyone's trying to do more with less to leverage AI, etc. So there could be a case to be made with a simpler site structure on headed, that more teams could be enabled to move a little quicker on that stack.
 
And then, there's obviously all the CFO pieces too. Just revisit those operating costs and your total cost of ownership, if you're investing a lot of money month over month just just to operate things. We're talking to one merchant where they're retaining month over month, and we're like: hey, in probably like eight months with that budget we could have you stood up on on a whole new headed structure. So having some of those thoughts and pushing around those considerations I think will be super helpful. The payback period is pretty prompt. You'd be surprised.

“Platforms evolve, needs evolve, architectures evolve. You just have to have the flexibility to evolve with everything."

What's one mistake you'd caution brands against when thinking about headless?

Sandor: Some brands are first-mover brands. They want to be the first in on new tech and tools. The lesson from what we've seen with a lot of merchants walking back is: you don't need to be the first mover all the time. Hold back, see how the market shakes out. Make sure your requirements are being addressed. Be requirements-based in your decisions, not tech-based.

If you had to sum up in one sentence, what has changed since that first headless wave?

Sandor: A lot has changed. Revisiting a headless decision isn't a step backward. It might have made sense at the time, and I'm sure it did for some of what merchants were trying to solve. But it might not be right looking forward. Platforms evolve, needs evolve, architectures evolve. You just have to have the flexibility to evolve with everything.

Bonus question: what are you reading, watching, or listening to?

Sandor: I'm a very bad sleeper, so I listen to a lot of podcasts, mostly sports-based ones that are boring enough to help me get to sleep. I also try to read a lot. I want to spend time away from my screen when I'm not working. When I do read, it's history books.

I just read a really interesting book about the changes that America went through from 1900 to 1950. I believe it's called The Big Change, by Fredrick Allen. It describes the change in America over those 50 years. Poverty rates, population growth, immigration, two world wars, technology. For instance, in 1900 there were really no cars, electricity was rare. It got me thinking about where we might be in 50 years time.

Richard Sandor is the Chief Revenue Officer at iamota, a boutique Shopify Plus premier agency based in Canada. iamota has helped more than 60 brands on Shopify, with deep expertise in subscription migrations and complex commerce builds. You can learn more at iamota.com.

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