Welcome to Executive Action Items, a Glossy+ member-exclusive series driven by monthly focus groups with subject matter experts. The bi-weekly series offers immediately actionable takeaways for workers navigating the rapidly evolving beauty and fashion industries.
This month, Glossy brought together founders from swimwear, intimates and jewelry brands to discuss how paid advertising strategies are evolving and how they’re preparing for AI-driven shopping.
Focus group members:
Bette Bentley, founder of Skimpies, the patented “strapless bra of undies” designed to feel like going commando while providing full coverage and support, created specifically for wearing under leggings.
Hayley Segar, founder of Onewith, a patent-pending swimwear brand designed to fit like no-show underwear. Onewith launched in 2021 and was featured on “Shark Tank” in January 2025.
Mike Cooke, founder of Sterling Forever, a 10-year-old women’s jewelry brand known for celebrity-inspired and designer dupe pieces, sold direct to consumer and through retailers including Nordstrom.
Paid ads and attribution challenges
Segar: “We repurpose our top Instagram Reels posts as Meta ads, with all the original organic comments intact. That’s been our most consistent paid strategy, and it works because it’s authentic content. Even user-generated videos can become top-performing ads when you secure rights to them.”
Bentley: “TikTok is great for instant results, but Meta still hasn’t clicked for us. I use Instagram as more of a brand billboard than a sales driver, but I’d love to figure it out. TikTok’s reporting lets me see exactly what moment made someone add to cart. That level of insight is harder to get elsewhere.”
Cooke: “We look at total P&L across channels because attribution is messy. TikTok drives awareness that lifts our Nordstrom Rack business, even if the direct ROAS on TikTok ads is break-even. That halo effect is real. Right now, everyone — agencies, creators, TikTok itself — is making money, except us. That’s why we’re building our live selling in-house to control costs.”
Preparing for AI-driven shopping
Segar: “We’ve already signed up for the ChatGPT shopping beta and optimized our site for AI readability. I’m fully anticipating that AI will be a major channel, the same way TikTok transformed awareness. The moment consumers can shop directly inside ChatGPT, I want us to be there.”
Bentley: “I use ChatGPT daily, and I’ve already noticed people mentioning it when looking for solutions. If a woman searches for ‘What underwear can I wear under leggings?’ I want Skimpies to be in that answer set.”
Cooke: “I hadn’t considered AI shopping until this call, but I’ve already had my team sign us up for the waitlist. It’s clear we need to adapt now before it becomes table stakes.”
