Like Steve said, definitely remove the reminder about the extension. That works like a roadblock to a successful purchase. What works well for me is - send a plain text email 5 days after the trial is over (if the user has not purchased) asking the user if he wants more time. This is not advertised on my website and has three benefits (i) I come across as really generous (ii) allows me to change this policy whenever I want (iii) allows me to only give this offer based on lead scoring.
Your checkout page looks fine. I like that you advise the user which plan to buy based on the number of boards he has. Anything you can do to save the user brain-cycles is a bonus.
I would add social proof by virtue of a testimonial on the pricing page. Since your customers are trading dollars for time, the testimonial needs to emphasize the number of hours they can save using Corello (saving 5 hours a month > $39). Since you don’t already have a testimonial similar to this - here is an easy hack to get one - whenever a customer is happy with your product, or you have solved some issue for the customer or provided great support, follow up with the customer asking specifically - how many hours they would spend a month manually doing what Corello automatically does for them. When they reply back with a number (they are incentivized to reply back due to your great support), ask if you can quote them on your website.
Another hack specific to your issue - since the users are signed in when they reach your checkout page, you can easily target specific users who looked at the page but did not buy. It could work like this - if the trial is over and the user checked out the checkout page and did not purchase for 48 hours, then send the user an email with a 20% off promo code that ends in 48 hours. Track how well this works. If this works very well, then there is an issue with urgency - e.g. maybe the users are not being cut-off from using the product after the trial is over.
Bonus Home page tips
- I find that I generally glaze over the entire testimonial section unless there is a picture of someone I know. It’s the same sort of banner blindness that makes you miss all the facebook ads. I would therefore remove the entire testimonial section and intersperse the testimonials throughout the home page. You can match each testimonial with a feature - For example right under the feature “Corrello gives you the high level view Trello is missing” you can put the testimonial where the customer says “Trello is great, but doesn’t have reports for me to see what is on everyone’s plate” - Boom! instant social proof of your features.
- Add some whitespace between sections - don’t worry about the vertical scrolling. Our mice have evolved to have wheels!
- Put the expedia testimonial right at the top where everyone can see the expedia logo. (I do not recognize any of the other logos/names. If any are more relevant to the niche you are targeting, use those instead)