Ask IH: I'm thinking about sending out a "What's new" newsletter to my subscriber list. What should I know?
I've been waiting for the right momemt to finally start to "annoy" my userbase with an automated email via MailChimp. I feel that I'm approaching the right time because I've just redesigned the blog, and realesed a few features that I believe are crucial.
My goal is to convert expired / non free trial customers to paying customers. What are the best practices for sending out a newsletter?
The best practice for this kind of effort is to have something worth saying.
It's one thing to have an email list, it's another thing to have an audience. The issue that most organizations face is that they start with an email list and never create an engaged audience because they don't prioritize valuable content.
It looks like you've published 8 blog posts since launch -- My focus would be developing a content calendar that highlights future posts (at least once a month) as that will ensure that you have something to share in addition to product updates. It's great to keep people engaged with your product but your audience (especially those who are expired/non free trial customers) will be looking for value.
So start there...
Can you create more 'How to' posts? Can you create resources that are valuable? Or maybe... If content creation isn't up your alley -- You could start curating content from other sites that your audience would find relevant. Think about stories, media companies, thought leaders, YouTube channels, etc.. That your audience loves.
Find their work and share this as a monthly (or weekly) update that also includes updates about your product sprinkled within it...