Recommend an Email Marketing Plugin

I’m looking to build a membership/subscription based site. I already have an existing custom programmed site. But I’m looking to use Woocommerce Subscription and Members plugins. However, I am open to a better solution/plugins.

My question is in regards to email campaigns. I need email a specific customer segment based off of previous & current purchases.
Example, sending an email to customers who purchased product X in the past, who are currently SUBSCRIBED to product Y.
The system needs to build this email list automatically without the user having to select individual accounts. I will have over 5000 active accounts at any given time. It will be very time consuming to manually build an email list.

Does any anybody have a recommendation of a combination of plugins to accomplish this task? There are so many affiliate blogs… I’m looking to hear real world input.

Thanks in advance.