So this is what I do, my results have been ok...ish.
Plugins I use are alidropship abandoned cart, mailchimp and mailmunch.
There are 3 basic funnel scenarios that are relevant to me.
A. Customer purchased (the object here is to alleviate buyers remorse and encourage repeat purchase)
1. Thank you for purchase email (alidropship automatic)
2. Tracking number email (alidropship automatic)
3. Related product / upsell promo email (I manually make these using mailchimp)
4. Leave a review promo mail (I manually make these using mailchimp)
5. Regular (but not to regular) niche related newsletter emails) (I manually make these using mailchimp)
6. Seasonal promo emails (I manually make these using mailchimp)
B. Customer abandoned cart (the object here is to get shopper to complete purchase. Some folkes spend more than I do - I hate spam so send fewer on principle)
1. Cart reminder email (alidropship abandoned cart plugin)
2. Discount mail (alidropship abandoned cart plugin)
3. Bigger discount email (alidropship abandoned cart plugin)
C. Shopper left without adding anything to cart (the object here is to get shopper to subscribe to newsletter)
1. Exit intent popup with discount (I use mailmunch for this)
2. Discount email with related products (I manually make these using mailchimp)
3. Regular (but not too regular) niche related newsletter emails) (I manually make these using mailchimp)
4. Seasonal promo emails (I manually make these using mailchimp)
Use popups sparingly. Don't spam people, they will hate your brand and your store. Imagine you are the customer. If the content isn't meaningful, your readers will ignore it. I keep my email short and to the point.
Hope this helps,
B