I have implemented a number of different solutions for similar models and found that Stripe is best (http://www.stripe.com)

If you are based in the US, UK, Ireland, or Canada, Stripe.com is going to be the best choice. Braintree (https://www.braintreepayments.com/) is another good option.

This depends on where you are incorporated. If you are a US company - paypal or stripe are good options. Merchee is another option.

If you are outside the US, your options are more limited depending on where you are incorporated.

There is so much more to this than simply looking at implementation and cost. Honestly, any number of recurring providers are going to be fairly straight-forward for a quality developer to implement with your service. Many of them will also likely be easy enough that you can implement without a developer using third party API tools like Zapier.

My Disclaimer
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I run a recurring business. Every customer pays monthly. We have one trial available, and the rest are basically monthly payments. We run Stripe to actually process the payments and deposit into our bank account, and we use Chargify to handle the recurring side of things.

Stripe can handle recurring on its own, but it's not as robust ( out of the box that is ) as Chargify - and I like the reporting and maintenance piece Chargify provides.

We have 500ish customers and plans ranging from $150/mo - $2500/mo.

What to Consider
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1) You need to understand what you need
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If you simply need a way to process credit cards online as a recurring setup, then yes, Stripe can handle that. You set it up yourself ( or hire a developer ) and just connect it to your bank account. Create your product and really that's it.

If you require more functionality like HTML / PDF statements for customers, customer portal and account management, automated Dunning process for collections and your accounts receivables ( when customer cards expire, they reach their credit limits, their bank declines charges, etc.. ), refund processing, chargeback support, upgrades / downgrades, proration, etc.., you're going to be looking at some more advanced ( and expensive ) solutions.

2) You need to understand what you get
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One of the most important things to consider is data portability. You're a startup, and it's likely you're not going to be with the first solution you choose for the long-haul. Right now, you're going for what fits the business and what you can affordably scale as you need to. Eventually you may want to move to another provider.

There are currently no regulatory requirements for payment processors to provide you with your data. What this means is that in 3 years when you want to switch, you many not be able to access your customer data and port that over to your new solution.

Imagine the nightmare you are going to have when you've got 300 customers that you have to ask to re-join your services because you don't have their credit card numbers anymore. I went through it with just 45 customers and it was a terrible experience on both ends.

PayPal is notorious for making this difficult, as is Authorize.net - they are probably the worst offenders. So read through the agreements and terms and make sure you can take your data with you whenever you need it.

3) What are the fees associated?
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You're going to be dinged multiple times - by the merchant account, by the payment gateway, and by the recurring system.

If you just used Stripe, you will be charged ~ $.66 per transaction each month with your current pricing. Not bad, but it needs to be priced into your services and planned for. If you add some subscription software like Chargify, you'll be charged monthly per customer count rather than per transaction, starting at $65/mo.

So Customer 1 costs you $65.66 per month to process their card using Stripe and Chargify. So the pricing is certainly a big factor.

4) Is this self hosted or not?
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Are you going to host the payment forms, or outsource that to your gateway / processor. Stripe is wonderful because you dictate the experience and customers don't have to leave your site in order to process their payments.

However, this also means you need a secure domain or payment page with a SSL certificate. These range from $10/yr to thousands ( you likely only need the $10 cert for now.. ).

In order to have a certificate you also need a dedicated IP address. That will cost you monthly as well ( shouldn't be more than $10/mo for that ), so now our Customer 1 costs you about $77 this month in just processing their card.

If you decide to use the processor hosted page you won't need SSL or the IP address, and this works like PayPal does - customer clicks to buy and is redirected to payment page.

5) Understand the Support and Uptime
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The last thing you need are payment processing problems. Whichever provider you look at, ask them for their uptime history and understand what type of support you get.

Some processors provide 24x7 support, but only for priority customers. Some provide general email / ticket support, so you just wait in line.

Put yourself in your customer's shoes and ask what you'd do if there were a payment problem ( billed multiple times, not billed at all, not sure if you're billed.. ) and then figure out how you'd resolve those issues from your provider side. Ensure your gateway / processor support aligns with your own.
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I hope this helps you a bit. Here are some links to get you started:

Stripe - https://stripe.com/
Chargify - https://chargify.com/
Braintree - https://www.braintreepayments.com/
Recurly - https://recurly.com/
PCI Compliancy - https://www.pcisecuritystandards.org/

If you have any other questions or want some clarification on something, feel free to request a complimentary call.

https://clarity.fm/justinknechtel/e
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