Hey Lindsay, Love a good onboarding tactical discussion :) 

Please look up the /email/new/email-campaign area for Automated Email campaigns.

You could config that Segment today using filters /users/overview

and can go on to set up a One-off email today and not an Automated email

So right now the process is manual and I will leave it to the CC Product team to communicate on possibilities available today and in the future.

Will all users who performed their last activity 2 weeks ago be contacted right away after constructing this email? If so, does that mean users who I want to setup the email for after 3 months also be contacted?

I’ve just been looking into this functionality. What I learned is that the email is only sent when users cross that particular threshold. So when you set up an automated mail for “users whose last activity was >30 days ago”, no-one is immediately emailed, even if they have been inactive for >30 days. Only when the a user hits that 30 day mark do they get the email.

Similarly, if you set up >14 days too, no-one >30 days inactive will get that email as well. It only gets sent out to a user when that user reaches the 14 days inactive mark. Not to everyone else.

That’s what I read, anyway, and trial+error confirmed that this is the way it works.