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I am a full-stack web developer interested in freelancing full-time. I am planning on billing clients monthly recurring payments for providing general maintenance of an application or website. For reference, I will likely host clients on Amazon Web Services.

I plan to manage dependencies, bug fixes, file and database backups, etc. This obviously wouldn't include the initial cost to develop the application and design the user interface. But I'm wondering what types of issues I might run into with a recurring billing model and how to overcome those issues?

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    Hello, welcome to Freelancing SE! I edited your post a bit to focus on the problem you're hoping to solve. On Freelancing Stack Exchange, our goal is to focus on Q&A. Hope this helps, and welcome to our site! :) – jmort253 Oct 10 '13 at 3:37
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I provide flat rate monthly support options for custom software I build. It includes:

  • Bug fixes
  • Email support
  • Research

The amount is different for each customer, because some applications are more difficult to support than others. Also the pricing depends on how quickly I guarantee a response - some are satisfied with 2 business day response, while others are looking for a response within 24 hours, any day of the week.

Things you'll want to address in your agreement:

  • Response time. (Make it clear that "response" isn't necessarily the same as "fixed" - you can't guarantee that things will always be fixed within a certain amount of time, as some problems may be outside your control.)
  • What is covered. Bug fixes? Answering questions about how something works? Small cosmetic changes? And make it clear what are acceptable contact methods. I don't want my phone ringing at 3am, so contact is supposed to be initiated with me via email. (I might speak with them later on the phone, but I'm not taking calls 24/7.)
  • How the contract ends. Mine are typically set up to require 90 days notice from either party, you may want to do something different.

Also, be cognizant of how much time this will really take. I set aside 25% of my time every month in case there are support requests, and I schedule other project work assuming only 75% availability. If support is needed for a client, I want to make sure I can still meet my regular project obligations. And I am careful not to take on more support clients than I can handle. Right now, I would not want to have any more than 4 support clients at any given time. Again - your circumstances may mean different limitations but consider what those might be.

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I use FreshBooks.com (no affiliation) which provides both of the features you need: recurring autopay billing and a support ticket system. For recurring autopay with a credit card, you'll need a payment gateway account. Otherwise, you can do the billing manually as long as you have the payment information on hand. Clients can log in and create support tickets (you set the permissions) or you can do it for them. Replies occur in a thread and you can assign the amount of time spent on a ticket.

For website maintenance subscriptions I offer a BareBones Plan, Basic Plan, and Custom Plans. The first 2 plans have very detailed and limited services spelled out. For instance, the BareBones Plan is basically designed to keep the lights on: WordPress core updates, plugin/theme updates, weekly database BAKs, monthly full site BAKs, and weekly security scans. Most of it is automated. The Basic Plan would include everything in Barebones plus some limited content-related services and troubleshooting. Both plans clearly state an hourly rate for requested services that are not covered by the subscription. A Custom Subscription is tailored to a client's needs.

The important thing is to clearly spell out your Terms Of Service (TOS) or Terms Of Agreement (TOA) in a document/contract that needs to be signed or accepted electronically. I state that a contract/subscription is considered signed and accepted once payment is received - which happens to be at the beginning of the covered month.

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I too am trying to build up the monthly payments. They are what keeps your business alive, in my experience I have found that the earlier you mention this the better. In your first meeting with a client bring the subject up, don't leave it till the end and say "Oh you want that? I need another stack of money" (unless you want to be the RyanAir of Web Design)

All joking aside, make sure you make the deal very clear, get your terms and conditions drawn up properly, and make sure you work out minimum terms etc. A shorted minimum term I have found is better, the client doesn't cancel if you do what you say you will but you do have the option to pull out should they start demanding unreasonable extras.

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