How ThirdLove uses AI to create a perfectly personalized fit.

Finding the perfect bra isn’t just about measurements—it’s about confidence, comfort, and feeling like yourself. ThirdLove understands this deeply.

For millions of women, bra shopping has long been a frustrating and emotional experience, often requiring compromises between style and fit. Co-founder and CEO Heidi Zak saw the industry’s shortcomings and set out to change them, launching a disruptive intimates brand known for its size-inclusive bras, half-cup sizes, and digital-first fit styling.

“We’re doing more than just selling a bra—we’re helping a woman on a journey,” she explains. “For so many, this is about reclaiming comfort and confidence in their own skin. That’s what truly matters.”

Curating human connection at scale

To make good on their mission, ThirdLove has always sought to create an experience that was supportive—both physically and emotionally—by prioritizing personalization at every touchpoint.

"I joined ThirdLove because I was drawn to the idea of customer experience (CX) being a core part of the business, not just an afterthought,” says Amber-Lynn Richey, ThirdLove’s Associate Director of Customer Experience. “Here, CX has a seat at the table alongside product designers and other key teams. This means we have real ownership, the ability to make meaningful changes, and the opportunity to build customer loyalty.”

Supporting customers as they make an emotionally-charged and individualized purchase requires a great deal of empathy. But during peak seasons, delivering that same level of care at scale becomes even more challenging. ThirdLove needed a solution that could not only keep up with demand but also ensure every interaction—whether it was about fit, returns, or styling advice—felt just as thoughtful and supportive as speaking to a real stylist.

Meet Barbra, ThirdLove’s AI stylist

To meet this challenge, ThirdLove partnered with Sierra to develop an AI agent built with the same care and intentionality as their bras. Unlike traditional chatbots, which often feel impersonal, ThirdLove’s AI agent—affectionately named Barbra—was designed to offer personalized guidance with the warmth of a real fit stylist.

“Previous AI customer experience tools always hit a ceiling because customers simply didn’t want to engage with them,” says Amber-Lynn. “Even with extensive implementation efforts, automation rates stalled around 20-30% as customers often felt like they were being ‘put in a box.’ Sierra, on the other hand, adapts to what customers are asking in real time.”

Amber-Lynn decided to deploy Barbra differently, embracing the flexibility and creativity of conversational AI. The team at ThirdLove has been intentional to ensure that Barbra isn’t just empathetic, but that she speaks the brand and customer’s language, avoiding industry jargon in favor of natural, intuitive phrasing. 

"We don't ask customers to use the traditional language of the industry, like asking whether they can fit two fingers between the band and their body," explains Amber-Lynn. "Instead, we use language that recognizes that fit is subjective. ‘Does it feel too tight, or just right?’"

To maintain this level of authenticity, the team reviews Barbra’s interactions daily, making small, continuous refinements—just as they would with a team member. “Because it’s built to adapt,” says Amber-Lynn, “those refinements are easy—allowing us to keep the conversation as intuitive and comfortable as our products.”

Scaling during holiday and summer surges

One of the biggest benefits of the AI-driven approach for retailers like ThirdLove is to support customers effectively during peak seasons. The brand typically sees two major annual surges: a spike around May as customers refresh their summer wardrobes and another during Black Friday, which extends through the holiday season.

“Interestingly, many of our customers, particularly moms, put off buying for themselves until after the holidays, so we see another rush in early December,” says Amber-Lynn.

Contrary to conventional wisdom, Amber-Lynn and her team designed Barbra’s initial use cases around the winter holiday rush.

"Peak seasons are always a challenge in retail—balancing a surge in demand, staffing shortages, and increased customer expectations,” says Amber-Lynn. “When we designed our AI strategy, we took what some might call a crazy approach: we launched it right over Black Friday, one of the most intense periods of the year. But we knew that if it worked then, it would set us up for even greater success in the spring, which is actually our biggest season."

This strategic deployment not only helped ensure that Barbra could handle peak-season inquiries, but also reduced the need for seasonal staffing. A key part of this was handling one of the most complex aspects of intimate apparel shopping—returns. Bras require a highly personal fit, making exchanges and returns inevitable. Barbra plays a crucial role in streamlining this process, answering sizing concerns, guiding customers through quick and easy returns, and even proactively recommending better-fitting alternatives.

In short order, Barbra was helping customers resolve an outsized number of cases. For a team that is committed to maintaining the brand's industry-high 92% customer satisfaction score, Barbra is becoming an essential asset to meet spikes in demand.

Personalization without limits

Looking ahead, ThirdLove sees even greater potential in AI-driven support. “When a customer visits our site, we want her to feel like she has a personal shopper guiding her,” says Heidi. “AI should enhance personalization, not just react to customer needs, but anticipate them.”

Amber-Lynn adds, “We’re exploring deeper AI integration—think AR-powered fittings, proactive customer assistance, and omnichannel support that makes every interaction feel as natural as an in-store experience. The more we refine Barbra, the more she becomes a real partner in delivering the experience we’ve always envisioned.”

ThirdLove has set a new standard in intimate apparel, proving that technology and human connection can complement rather than compete with each other. By embracing AI in a way that enhances, rather than replaces, the emotional and personal aspects of their brand, they’ve crafted an experience that truly meets women where they are.

“This isn’t about automation,” says Heidi. “It’s about making sure every woman feels understood, valued, and supported. AI should make a brand feel more human—not less. That’s the future we’re building.”