Optimize email marketing campaign

My friend, John, asked me today:

I run an online business selling digital products (software) for individual real estate investors. My products are both available in a free version (with limited features) and a premium version (with all features). The fee version helps me build an email database to target users for potential upsell of my premium products.

I’m in the process of setting up all kind of automatic emails to maximize the value of my customer email list and I would like you opinion on it. Currently I have the following automatic emails:

• cart abandonment (automatically sent if a user does not confirm the purchase) – Sent 1 day after signing up without completing purchase
• Upsell Email (to offer premium product at a discount) – Sent 1 week after purchase of free product
• Feedback email to premium users (asking to fill out a short customer satisfaction survey) – Sent 2 weeks after purchase

Question 1: What additional emails should I send? I’m thinking about an email to ask customers for their reviews online (trustpilot, etc) but maybe it should go in the same email as the satisfaction survey?

Question 2: I don’t have any cross-sell email because my products are quite different and I’m not sure a user of one product would necessarily be interested in the other products I offer. Maybe I’m wrong and should set up such email anyway?

Question 3: The survey email is currently just sent to users that purchased the premium product but I could, in theory, also send it to users of the free version. What do you think? (That would increase the reach considerably)

Question 4: In terms of sequencing, how long after purchase should I wait to send each of those emails? Currently I’m waiting 1 week for the upsell email but I’m afraid it’s too long. On the other end, given that the product is a software, it takes some time for the user to get familiar with it. Same question for the survey / feedback email that is sent 2 weeks after purchase.

That’s all I have for now, appreciate any feedback on this strategy!

Here’s the recommendation I gave John and I think It’d be helpful for some of you:

There is no such thing like a fully optimised strategy, at least not at the stage where you only start experimenting with flows.

The fact that you implement and think about it is already a very positive sign.
Just test and see what’s working and what’s not. Nothing is set in stone here but as long as your customer’s journey falls into a logical sequence and your copy is right there is no threat of alienating or scaring your customers away.

From what you’ve said I’d definitely add some abandonment cart emails (3 within the first 48hrs is a good start without breaching any legal rules in most countries).

Upsell emails – most definitely yes, I wouldn’t wait that long though, but I’d attack nearly from day one offering a time-limited discount.

Cross-sell – only if your products complement each other. If any other product would help them with the problem related to the product you’re offering, then I’d consider that but if you don’t have any sensible plan for it I’d leave it for future campaigns – at least you’ll have a reason to contact them later on.

I’d add review-gathering flow – min 2 emails (one is usually not enough, people need some encouragement or at least a reminder). Here’s where copy plays a big part, give them a good reason to do so and you should see some effects. And yes, I’d ask for feedback in the very same email rather than keeping them separate.

Yeah, play with it a little bit, add some emails on. Just make sure your copy has a human touch and it all makes sense and your sales will definitely benefit from it.

Hope that helps.

Thanks