1) I would set up a MailChimp account, for free. It’s the industry leader, it’s the best performer (in my experience) and it’s the most pleasant to use from a UX/UI standpoint (which matters a lot to me). It’s also entirely free from the get-go, up until a couple thousand subscribers. It’s a “no-duh” piece of software. This let you easily segment your lists depending on sign-up locations, or sign up types. If you have email resources to push subscribers – like Bidsketch does with their proposal templates – you can easily segment the users that sign up there, apart from the users that sign up straight from your blog.
Instead, I’m talking about timed pop-up ads, or onsite retargeting. After a user spends a certain amount of time on your page, she can receive a pop-up relevant to the content on that page, or to her behavior. Examples include exit pop-ups, which appear when a user tries to leave the page, or scroll pop-ups, which appear after the user scrolls a certain percentage down the page.

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