How about a free tier? Both MailChimp and MailJet have it, and the guy is going to pay for SES anyways.
Also, I'd reach out to AWS guys and ask them to provide $50 (or $20 - whatever they agree to) credit to every customer that signs up for your free tier since that'll lead the guys sitting on the fence to explore your product.
You can also think of adding a pay per use. Since you are talking to a price conscious audience (the non price conscious ones are already using MailChimp). Maybe $5 per use (unlimited mails).
I think your right the initial entry is a bit steep. The thing that scared the crap out of us with mailchimp was that there was no end in sight for price increases. If they had a max of $500 then we may have stayed on mailchimp. I guess our thought process was if you start with us you'll never leave because our prices will top out. But yes I think we'll introduce $5 for the first 1000 to get you going something like that maybe?
Pay per use is a difficult one, I think once you start complecting the pricing model like that people don't know where they stand. Personally I prefer simple.
Also, I'd reach out to AWS guys and ask them to provide $50 (or $20 - whatever they agree to) credit to every customer that signs up for your free tier since that'll lead the guys sitting on the fence to explore your product.