I would be very hesitant to go with the AWS/Heroku pricing route. A major selling point for PythonAnywhere is simplicity. Sign up, select your Python web framework, and that's it - time start coding. With AWS and Heroku, there's a learning curve, there's jargon, there's information overload you need to deal with first before you can use it. It takes an experienced developer/sys admin to successfully navigate through this level of complexity.
And PythonAnywhere's target customers are not necessarily AWS and Heroku's customers. You guys sell simplicity, not flexibility. The core of your customer base (I'm guessing) lies with the weekend hacker and novice developer crowd. And you don't want to scare away these customers by asking upfront how much storage or how many workers I need. Damned if I know. I'm not even fully clear what a worker is in the first place.
So the way I see it, there's two good options here.
Option A - Offer 5 or so different plans, ranging from around $9 for the entry level plan to $200ish for the enterprise level (helps serve as a price anchor). Best examples of this pricing scheme in action: https://www.linode.com/ and http://www.wufoo.com/signup/ . Consider eliminating the $5/month level plan or finding a middle ground between the $5/month and $12/month level. You're probably losing a good chunk of change here with such a low price point.
Option B - Offer one $9-$15ish/month base plan, but offer upgrades for diskspace, bandwith, memory, and a dedicated IP. Best example of this pricing scheme in action - http://www.webfaction.com.
Either pricing strategy could be successful. A/B testing is the name of the game, though. Some random thoughts about your current pricing table:
- Give concrete examples of what each plan would be appropriate for - "good for running a Flask app with xxxx database queries a day and xxxxx visitors a day", "recommended for small scraping scripts", etc.
- Change the color scheme of the table, a la Wufoo style, to help differentiate each plan
- Testimonials exist for a reason.
- Put the Beginner account to the left of the Hacker account to better explain the feature differences between the free/paid plans.
- Logos of the websites/newspapers you've been featured in at the bottom
- Take the information from the comparison table and put it into the pricing table. Then explain what a worker is, what Dropbox integration entails, how much Bandwith does my website need. Once again, look to Wufoo.
- Get an annual plan once you've solidified your pricing.
- Create a "buying FAQ" to clear up any misconceptions, reduce purchasing anxiety
- Graphically stress the "no-quibble 30 day money back guarantee" on each plan or on the Paypal buttons
Try some of these suggestions out. You can probably double or triple your conversion rate with a few months of A/B testing.
Food for thought: http://www.kalzumeus.com/2012/08/13/doubling-saas-revenue/