Trial email schedule

The users of my saas app have a 14 day trial run to decide if they like it enough in order to stump up the cash for a monthly subscription.

I'm trying to work out a schedule of emails to send the users during this period in order to maximize conversions to a paid plan. The question is: what is the right amount of emails to send without feeling spammy or overbearing?

My current thoughts are:

• Email on signup of trial, "welcome to your 14 day trial"
• Email 5 days before trial expiry, "your trial is about to expire so subscribe"
• Email on expiry "trial expired, subscribe to continue"
• Email 7 days after expiry, "look at the cool stuff you are missing"
• Email 14 days after expiry, last email, "special offer, 20% off if you sign up today"

Does this seem reasonable? Too much? Too little? Just right?

Answer - it depends.

• On your market
• Your customers expectations
• Your app
• Your email content
• The prevailing winds

Experiment and measure is the only way.

(More actionable advice - that seems reasonable but the key is that the first few emails have to have something useful in for the subscriber. Tips on setting up, how to get best use etc)

There should be a way to opt-in and out. Then: 1) Send a message for first usage with a suggestion on some other feature theyou could try. 2)Send a message of they have not used it for 1 week. 3) Send a message a day or two before it expires.

They should be able to opt out at any time. Pay attention to how this is working. If too many people opt out, change the frequency and/or make sure you explain how often you plan on emailing them. Don't let their fears get the worst of them so they think you're going to send something every hour. Keep them informed.