Automatic renewals or not?

I stressed out about this in the early days, but I now realize I was just overthinking it. It seemed like just assuming someone wants to renew is presumptuous, but now that I've done it a bunch, it's clear that customers won't think that. I think it's good to leave room for discussion so if they do want to cancel, etc. they know they can talk to you, but I think it's best for the email to seem as routine as possible.

I've used copy similar to:

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Hi [FirstName],

It's been almost a year since you started using ReviewTycoon. Thanks so much for being a loyal customer during that time! Your renewal date is coming up in 30 days, so I just wanted to give you plenty of lead time so it doesn't take you by surprise.

I've attached an invoice which you can pay any time between now and [EndDate]. The invoice has all the details, but just as a reminder, ReviewTycoon costs [Cost] per year, and that includes [a few primary benefits of your product/service].

Please let me know if you have any questions about the invoice, or anything else related to ReviewTycoon!
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It might seem a little too direct to just assume they want to renew, but I've sent a bunch of emails like this and it's literally never been an issue. If they want to cancel, they'll tell you that, but they won't feel offended that you thought they'd want to renew. You'll also probably want to have a series of reminder emails before you completely lock down their account just in case the first one slips by them.

I also love what @louisswiss suggested about segmenting your customers and sending them different emails based on their usage. The only thing I'll add is that you shouldn't assume someone won't want to renew just because they haven't been using your product. This probably differs by industry, but at least in my industry (CRM) a lot of people know they should be using it and the annual renewal might be the kick in the pants they need to get serious about it.

From the perspective of your customers I would definitely want an email or some kind of notification that my account is about to expire. Even if you had recurring payments set up I would want to know so I am not surprised by a $1000 bill or automatic payment.

If they show signs of churning, might be a good opportunity to discover why they are churning and what changes can be made to bring more value to them and others.

Good luck!

Maybe an email 30 days before the end of their paid period saying something along the lines of “your licence is about to expire, if you wish to renew please pay for another year otherwise your account will be deactivated on X date” (but worded a bit nicer) then another reminder a week before if they still haven’t paid or replied, then another a day or so before the expiry date.

Then it’s more like a reminder but you’ve also covered yourself if they don’t pay up by letting them know several times that their account will be deactivated.

So the default (assuming you don't contact them at all) is that they pay nothing and churn, right?

How do people pay you?