How can I automate follow-up emails for carts abandoned more than once?

I'm pulling my hair out with cart abandonment. We're a growing fashion accessories brand, and our monthly ad spend is around $15,000. Our conversion rate hovers at a frustrating 2.5%, but what's killing me is seeing the same customers abandon their carts multiple times. It's like they're window shopping but never committing. I've tried generic 'come back' emails, but they feel impersonal and frankly, they're not moving the needle. Our products aren't cheap—we're talking $80-$250 per item—so each abandoned cart represents serious potential revenue. I need a smarter approach that doesn't just blast everyone with the same message. I want something that understands why they're hesitating and offers a truly compelling reason to complete the purchase. Right now, it feels like I'm throwing darts in the dark, hoping something will stick. Our team tracks every metric religiously, and these repeated cart abandonments are a massive leak in our sales funnel that we desperately need to plug.