This Founder Calls Every High-Value Customer. AI Tells Her Who.

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*Glean, Work AI Index 2026

This week I interviewed Hillary, the founder of Wardrobe at the Cross. She runs a clothing boutique and an online store for women over 45. Honestly, the last brand you'd expect to be running serious AI automations. She's running them across the whole business.

One of them stuck with me because of how simple it is.

Her customers need a lot of nurturing before they buy. Most of them visit the site 4 or 5 times before placing an order. So whenever someone places a big first order, Hillary or someone from her team calls them personally to welcome them and make sure the sizing is right.

Finding who to call was the annoying part. She was going into Shopify every day and checking orders by hand.

So she automated it. Here's her explaining it on the podcast:

The AI goes through her orders every morning, picks out the customers worth calling, and puts a slot in her calendar with the phone number, what they bought, and a small script. All she does is make the call.

And that call saves her real money. If someone ordered jeans in a size 30 and she knows they run tight, she offers to send the 31 instead. The return never happens.

We rebuilt her exact setup in Claude Cowork.

The full walkthrough is in the paid section below. Takes about 15 minutes to set up, then it runs every morning on its own.

Every store has dead links. Say you enter a URL with a typo. You will either land on a page that says 404 error, page not found or you will be redirected to the home page.

Fresh Clean Threads sells t-shirts on the error page instead.

Type any broken URL. I typed https://freshcleantees.com/S

Instead of getting and error i got:

"Oh Shirt!"

Then no apology at all. "We found super soft threads you might've actually been looking for." And below it, the whole catalog. Crew necks. V-necks. Polos.

A wrong turn becomes a shop window.

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