Retention Edge E34: Pop-ups, AI, and the shift from acquisition to retention

Sarah Sathaye has been with NAADAM and its portfolio brands for a decade. They've scaled to pop-ups in New York, LA, and Chicago. They have a product line that practically sells itself on repeat. And until this month, they've never had a loyalty program.

This week I sat down with Sarah to talk about why, what changed, and how she's thinking about AI, physical retail, and driving repeat purchases in a business where you're always fighting to reacquire customers.

Here are my top takeaways from the episode.

Pop-ups as a retention channel, not just a revenue play

NAADAM's business is seasonal. Instead of committing to permanent retail, Sarah's team opens pop-ups in August or September and closes them at the end of January.

Smart. But what caught my attention was how she frames it: pop-ups are a marketing channel and a revenue channel.

The stores in NYC, LA, and Chicago aren't just about selling sweaters in Q4. They're building the kind of in-person connection that makes someone come back to the website in March.

Physical retail feeds digital loyalty. You think of pop-ups as temporary, but NAADAM uses them with long-term retention in mind.

If you're a seasonal brand sitting on the fence about retail, the pop-up model is worth studying.

They're launching a loyalty program this month

One thing Sarah said I think is particularly relevant right now:

"We are in a business where we are constantly going to always have to acquire a really significant chunk of our customer base every year."

That's the reality for a lot of brands. Especially in categories where the product lasts. A cashmere sweater isn't a monthly purchase.

So for 2026, they're going all in on loyalty. First official program ever. It's one of their top goals for the year.

Why now? Because they've hit the point where acquisition alone can't sustain growth.

Sound familiar? If you're still running without a formal loyalty program, ask yourself: are you leaving repeat revenue on the table just because you haven't built the structure to capture it?

AI adoption starts with giving your team space to experiment

Every brand is looking at AI right now, and trying to find the right way to use it to 10x revenue and halve expenses.

The reality is sometimes a little behind the hype.

Sarah's team is using AI for segmentation, PDP imagery, color correction. A lot of practical things; not culling headcount and reimagining their company as AI-native.

She was honest about how they’ve incorporated AI so far: "I won't go out on a limb and say that we've done that perfectly around the organization yet."

Her focus is on driving adoption internally. Giving people space to learn and experiment before mandating anything.

That's the right order. Most brands buy the tool first and figure out adoption second. The ones getting real value are doing it the other way around.

Your website needs to answer questions like an AI would

This was the most forward-looking part of the conversation.

With AI becoming mainstream, shopping habits are going to change. Not massively - the age of autonomous shopping agents isn’t here yet - but in some minor, but notable ways.

1. AI is changing how customers discover products. Search queries are getting more conversational, more specific, more personalized. Your content needs to match that depth.

2. Customers are going to start asking your website questions the way they ask ChatGPT. If your on-site experience can't handle that, you'll lose them.

It’s not an enormous shift, but it’s enough that you can get left behind if you’re still building your site with 2024’s playbook.

VIP treatment doesn't have to be complicated

When it comes to driving repeat purchases from their best customers, Sarah keeps it simple: proactive outreach with things they can't get elsewhere.

• Holiday gifts

• Early access to new drops

• Special sale access

Nothing revolutionary. But that's the point. Your VIP customers don't need a complex program. They need to feel like you actually know they exist.

Sometimes a well-timed email with early access to a new collection does more for retention than any points system.

The most important thread running through all of this: NAADAM is a brand that's been acquisition-first for a decade and is actively making the shift to retention. 

Loyalty program, pop-up strategy, AI experimentation, VIP treatment. It's all part of the same move.

If you're at that inflection point too, this episode is worth your time.

You can catch the full episode on YouTube or Spotify. Wherever you watch or listen, be sure to like, comment, share if you found it useful.

I’ll back later this week with more to help you grow & scale your brand the right way.

— Pietro

PS - Want to see what your store would look like as a mobile app? Get a free preview here, or shoot me a DM on LinkedIn.