Case Study: How JOLYN Increased Winback Conversions by 9x with AI Agents
Learn how JOLYN used Monocle’s AI agents to personalize winback timing and messaging, turning dormant customers into repeat buyers without sacrificing margin.
9X
increase in conversion rate from winback flows
+15%
lift in average order value from reactivated customers
5
winback audiences
about
JOLYN is a Southern California–based swimwear and activewear brand founded to reinvent women's competitive swimwear. Designed for athletes, their suits and apparel combine high-performance fabrics with bold, stay-put styles that thrive in saltwater, sun, and chlorine. Committed to sustainability and community, JOLYN supports ocean conservation, uses eco-friendly packaging, and uplifts women through athletic sponsorships and mentorship.
“There’s no way we could personalize each customer touchpoint manually. It’s completely changed how we think about reactivation.”
The Challenge
JOLYN struggled to identify which lapsed customers were ready to repurchase, leading to mistimed outreach and unnecessary discounts.
With over 1 million subscribers, JOLYN needed a smarter way to re-engage lapsed customers without relying on blanket discounts that cut into profit margins.
The core challenge is that swimwear isn’t a weekly purchase. Some customers return within months, others not for years. JOLYN couldn’t easily distinguish between truly churned buyers and those simply not ready to purchase again.
As a result, reactivation emails were often sent when customers weren’t ready to purchase, or included content and product offers that didn’t match their interests. This led to missed revenue opportunities and unnecessary discounts targeted at the wrong audience.
“We’ve always struggled with winbacks. Only 2–3% of first-time buyers return, so it's like trying to find a needle in a haystack. And even then, figuring out what offer will actually draw them back is another challenge.”
The Solution
Monocle’s AI agents identified the best time and offer for each lapsed customer, triggering personalized emails through Maestra without manual work.
Monocle’s AI agents continuously analyze real-time behavior, including past purchases, on-site engagement, and contextual signals, to determine the ideal timing and offer for each individual. The platform also leverages zero-party data collected during signup, such as preferences for beachwear vs. poolwear, to tailor product recommendations based on each customer’s interests.
When Monocle determines a customer’s likelihood to repurchase is high, a webhook triggers Maestra to send a personalized email with the optimal offer and curated product picks, no manual segmentation or guesswork required from JOLYN.
“Maestra and Monocle solve that puzzle together. Monocle's AI pinpoints the right timing and offer, and Maestra handles the personalized messages and recommendations.“
The Results
9X
increase in conversion rate from winback flows
+15%
lift in average order value from reactivated customers
5
winback audiences
The Results
JOLYN boosted winback conversions and order value by personalizing timing and offers with Monocle’s AI agents.
By using Monocle’s AI agents to time and personalize each winback touchpoint, JOLYN turned dormant customers into high-value repeat buyers, boosting retention without sacrificing margin.
Beyond the immediate lift in conversions, the new winback strategy helped JOLYN strengthen long-term customer relationships. Personalized winback flows reintroduced customers to the brand on their terms, leading to higher engagement with ongoing campaigns and more consistent post-purchase behavior across channels.
