Sharp low price points are really helpful for family shopping, Stitch Fix CMO says

Last fall, online personal styling service Stitch Fix initiated its Retail Therapy rebrand as the answer to what Stitch Fix CMO Debbie Woloshin described as “broken” shopping experiences—for instance, when customers hit the mall for needs like special occasions or body transformations and come home empty-handed.

Stitch Fix launched Retail Therapy as part of a rebrand into a new tone of voice and look connected to its message of personalization, community, and AI-enabled human styling. At a high level, the concept tackles how in-store shopping has lost its personal touch, leaving customers either begging for help in messy dressing rooms or drowning in endless online options.

In its third iteration of Retail Therapy, Stitch Fix found that 95% of men liked the idea from a convenience perspective and 90% of men found it fun and motivating to try Stitch Fix. Among women, 89% found the campaign appealing and 85% said it was relevant—the platform's highest relevance score with women ever, Woloshin said.

We caught up with Woloshin, who has now been at Stitch Fix for three years and goes on to the site at least four times a day, on the sidelines of Shoptalk Fall recently. “As we build upon the messaging of Retail Therapy, it’s resonating,” Woloshin said. “We see it in watch time, in engagement.”

This interview has been lightly edited for length and clarity.

In terms of holiday strategy for Stitch Fix, how is discounting evolving?

Having really sharp and low starting price points for kids has been really helpful for family shopping. We just launched something called household accounts, where you can shop for your family. That does three things for you: It takes the burden of time off your shoulders, you have great support, so it saves you a lot of focus from a budget perspective. It also makes sure that your husband doesn’t show up at Thanksgiving looking like he’s at the wrong holiday. That’s another thing that we’re going to be doubling down on, and that’s also great from a gifting perspective.

Last year, we saw the holidays start earlier, and we saw a lot of discounts with incremental, like 30% off, take an additional 15%. We’ll do that at some level. We’re going a little bit more lightweight on holiday messaging versus value messaging. We’re not talking about Christmas or gifting. We’re talking about getting ready for the season. We met with our clients, and we did a lot of focus groups, and we heard from them that they’re looking for quality and value and that they’re willing to make the purchase if it’s worth it. What we see a lot is that our private label brands have a lot of that benefit built in, and we have seen some really good traction there, so we’ll be making sure we push that out.

We have a very robust plan with lots of great themes tied to partnering with your stylist, gifting your family, gifting your friends, and a lot of fun discovery. And we’re leaning in on how we can make the holidays easier and better for you. We’re trying to take decision fatigue off their shoulders. They don’t need to make any more decisions. And we’re trying to make shopping easier for them, so that they don't buy the same item on repeat because they’re too afraid that they’re going to have to return something.

What is a key focus for Stitch Fix going forward?

What we’re doing is doubling down on the evolution of what community means—how we have built a really strong sense of personal as well as personalization within our service and really bringing the stylist more than ever out behind. They were really sort of hidden behind the curtain, and we really are bringing them out more.

We’re seeing that there’s opportunity to really amplify. Our stylists are our frontline. They are the heart and soul of the business, and they are what makes the connection between our clients and even internally, this incredible sense of community. We’re looking to make sure we scale that.

How are Stitch Fix stylists dealing with the pace of evolution of AI?

I would say that the whole company is embracing the opportunity to evolve, and what that looks like for us is providing a suite of tools to our stylists as well as to our clients to enable either better connection, better service in terms of what they want to ask for, in terms of their outfitting, and better visualization.