Jenna Flateman Posner has sat on both sides of the retail technology equation: as a retail CDO and as a technology operator. That’s exactly why her perspective on the AI moment we’re in carries weight.
Now, as Co-Founder and CEO of Chief Digital Agency, she has a view under the hood of a dozen retailers at once, watching in real time as organizations try to figure out how to move with urgency without losing the plot.
In a recent conversation, she didn’t pull punches about what she’s seeing.
Having a Roadmap Is Not the Same as Being Ready
One of the things I’ve heard talking to some retail leaders is a version of, “We’ve got our AI roadmap, so we’re covered”. But in Jenna’s view, that level of confidence is actually a warning sign.
“The reality is that staying on top of this is such an unbelievable challenge that that sentiment in itself is going to leave that retailer in a lurch. It can’t be static right now. It just can’t.”
She describes the current environment as “whiplashy.” Retailers are taking cues from the major platforms, and when those platforms reverse course (she points to OpenAI’s rollbacks on shopping-specific features and Instant Checkout), the organizations that locked in a fixed plan are suddenly unmoored. The signals are changing daily. Figuring out which ones to react to and which to wait out is its own full-time job.
This doesn’t mean that retailers should be paralyzed by indecision. But there’s a meaningful difference between being in motion and being finished. The companies best positioned for what comes next are the ones that stay curious and keep adapting, not the ones that feel done.
The Case for Moving Early—and Not Just for Technology Reasons
The conversation about AI in retail tends to focus on what’s being built and deployed. Jenna thinks the internal transformation—how organizations feel about AI, not just how they use it—is being underestimated.
“There’s so much that we have to get over: the fear, the uncertainty, the concern about our jobs. The sooner that brands [start] to adopt AI, show its value, help establish trust within the organization… the sooner we can get to a place where now we’re talking about adopting AI across the entire business.”
She points to Ekta Chopra at e.l.f. Beauty as an example: a leader who moved from CDO to CTO/Chief AI Officer not because a title was created for her, but because she earned the organizational trust to hold it. That credibility takes time to build, and it compounds.
The practical returns on early AI investment eventually show up in the numbers. But every month spent building internal fluency, working through the cultural resistance, and demonstrating value is time that can’t be bought back later.
The companies that wait won’t just be behind on the technology. They’ll be behind on the trust.
Build vs. Buy, and the Dangers of Spreading Too Thin
A lot of the conversations I’m having right now are circling back to something that we’ve been debating as long as I’ve been covering the industry: build versus buy. Given her experience on both sides of the aisle, Jenna’s take is nuanced.
“I think there’s a nice hybrid scenario here where you can continue to flex your own ability to innovate and build internally while still getting the benefits of working with technologists that are just experts.”
Her core conviction: vendors build to solve specific, quantifiable problems, and problems that cost money are easier to build a business case around than a broad AI strategy. That relationship still has real value.
But there’s a related tension: when implementations are lightweight enough to spin up and swap out quickly, it’s easy to end up with too many vendor relationships to manage well. And when you’re spread thin, the casualty is partnership.
Her advice isn’t to consolidate everything—she’s seen what happens when a retailer’s overly reliant on a single vendor. It’s to be deliberate about which relationships deserve real time, energy, and trust.
Ecommerce Is Moving Into a New Gear—and the Engine Might Not Be What You Think
The most striking thing Jenna said in our conversation wasn’t about a trend. It was about a moment.
She was walking through a client’s integration into Perplexity, and mapping out the flow: product feed, order creation, conversion, path to fulfillment. And somewhere in the middle of that exercise, it hit her.
“There’s no ecommerce engine in here. There’s no Shopify, there’s no Salesforce, there’s nothing. And I was like, oh my God, we’re here.”
It’s the vision she’s been describing for years: commerce that isn’t beholden to the browser, to the monolith, to the generic search engine. A consumer who can transact wherever intent shows up. In that conversation with her client, she watched it become real.
But Jenna’s biggest point remains simple. “Horribly challenging and unbelievably exciting” isn’t just a description of the moment. It’s a choice. The organizations that treat it as the latter are the ones that will define what comes next.
Author
Krystina Gustafson
Co-Founder & Co-CEO, RetailClub
Krystina Gustafson is the Co-Founder and Co-CEO of RetailClub, the only retail event built on the conviction that AI isn’t just transforming the industry, but is reshaping the economy, society, and culture that underpin it. She was previously SVP of content at Shoptalk and Groceryshop, a retail reporter at CNBC, and a web editor at Women’s Wear Daily.
Disclaimer: This article was written by me … with the help of AI (Claude Sonnet 4.6, to be specific). If we’re building an event about how AI is transforming retail, we’d be hypocrites not to use it ourselves. At RetailClub, we’re testing and deploying AI at every stage of the business: from how we research and write, to how we design, plan, and deliver events. And no, I refuse to stop using em dashes. I’m a former reporter. I was overusing them long before AI showed up.
