Your Six-Month Checklist for Subscription Success

April 17, 2019 · 9 min read

One of the biggest draws of starting your own subscription-based service or product is the idea of “set it and forget it” recurring revenue. But setting up any kind of business takes work, time, and intention – and avoiding many potential pitfalls along the way.

If only you had a checklist for the must-do items in the first six months of your business…like the one below. Following these guidelines will help you set the stage for success and build a strong foundation to your business:

The first month

The first month of starting any business can be pretty nerve-wracking, but especially so for subscription e-commerce. For our purposes, we’ll assume that you’ve:

  • Already chosen your niche
  • Figured out what specific problem you’re solving
  • Started to get clear on your unique selling proposition and the benefits of your product

(If you haven’t completed that “pre-work,” Practical Ecommerce is a great resource.)

In your first month, you’ll want to:

  • Build a website
  • Figure out how to accept payments safely and securely
  • Have a marketing strategy in place

Choose your website platform

The first step is building a website so that people can learn about your business, buy from you and subscribe to your email list. If you want to write weekly blog posts about your experiences or to give advice, your website is a great place to park it. Developing a great website will impact your and your customers’ experience going forward, so be sure to choose wisely.

WordPress (which you can use self-hosted or hosted by WordPress) is the most popular CMS, or content management system — basically, the interface you use to build your website. Because of its popularity, you can find plenty of tutorials for it, along with themes and integrations for it. (Including the Rebilly for WordPress plugin!) It’s also easy to find contractors at a variety of prices and skill levels who specialize in it.

If you go with self-hosted WordPress, Flywheel is a managed WordPress host that makes the process seamless. If, for whatever reason, WordPress isn’t for you, you might take a look at Squarespace as an alternative.

Choose and set up your payment gateway and merchant account

Obviously, this is a necessity for getting paid! We’ve already written an article to help you navigate that process, so make sure to check it out and choose a payment gateway and merchant account that fit your needs.

Choose your subscription billing management software

Once your website is set up, how will people sign up for a subscription? This is where subscription billing software becomes important, as you’ll want to make the payment process simple for you and your customers. And it can provide other benefits, too. For example, if you lose a merchant account, billing management software can help you route payments to a backup gateway, so payments never get interrupted and your subscribers aren’t inconvenienced.

What to look for? PCI compliance, multiple payment options, payment gateway integrations, secure card vaulting, and much more. If you want a full rundown of exactly what to look for from a subscription billing software, check out our Six Must-Haves guide.


Your awesome website with easy payment options won’t do much good if no one knows about it. There are many marketing tactics you can use to drive your product’s usefulness home to consumers and traffic to your website, but a few options include:

  • Social media marketing
  • Email marketing
  • Content marketing

Choose your social media channels

Depending on what your business is, you’ll want to adjust your social platforms accordingly:

  • For a B2B company, LinkedIn might be the best option.
  • If you’re selling a beauty or fashion box subscription, Instagram is probably a good bet for your audience.
  • Facebook or Twitter are always a solid bet for someone trying to reach the widest cross-section of people.

You’ll also want to create a way to keep track of both social media efforts and all of your other marketing efforts — Airtable has a lot of free organizational templates for this.

Choose your email marketing tool

Not only is email a great way to let current and potential customers know what’s going on in your business, but it also allows you to keep up communication should your customers need to get a hold of you. Check out our email marketing tool suggestions here.

Begin establishing yourself as an expert through content

Content is an important part of a modern marketing strategy and helps with your search engine rankings in the long run. Aim to answer questions that your potential customers would have (whether about your product, the industry in general, or problems related to your product) and create useful, actionable content. For search engine rankings, Hubspot has a great list of suggestions for how to optimize for SEO.

Three months in

Three months into the business, you’ll want to focus on the feedback you’re getting and adjust your processes accordingly. It’s all about refinement. How can you make things better? Consider these three areas:

  • CRM Tools
  • Onboarding Processes
  • Shipping/Logistics

Choose your Customer Relationship Management (CRM) tool

You’re looking for leads, or you’re getting leads, but you need a better way to see the bigger picture and capitalize on opportunities. Look for a (CRM) tool like Pipedrive or, if you’re a bigger operation, try Salesforce to help you build and maintain those relationships.

Define and improve your onboarding processes

You got people to sign up, but are they staying? Many businesses are all about their prospects, but then seem to forget about them once the initial deal is done. During the first few weeks of getting a new user, you need to be just as focused on their experience as you were during the sale, if not more so. This is where customer onboarding processes can make or break your churn rates.

Evaluate and improve your delivery, shipping, and logistics processes

At this point, you should also be aware of any hiccups in your shipping or logistics operations, if you are selling a physical product (like a box subscription), are your customers getting their orders when they are promised to arrive? And are your refund and return policies easy to understand?

Logistics company Shippo offers the following advice:

  • Double-check the orders before they leave
  • Offer flexible shipping options
  • Be transparent about your shipping rates up front to avoid problems

For services, this is your opportunity to evaluate how they are being delivered. How well, quickly and easily are users able to access your service? Do you have a SOP for every step of the process to make sure nothing gets missed and every customer gets the same (great!) experience?

For digital products, there’s a lot you can completely automate, but this is a good time to double-check all of your automations and integrations, and make sure they’re working as they should be. Go through the entire process as a new customer and note any places that can be streamlined.

Look at other processes and automate what you can

While you’re looking at your customer relationship, onboarding, and logistical processes, don’t neglect other areas. Marketing in particular has a lot of ways to be automated without decreasing the quality of your results. Traditional automation software is expensive, but using tools like Zapier and IFTTT, combined with the other tools (like Buffer or Airtable) that you might already be using, you can get a head start.

You can also look at your customer service and communications in general. Obviously, you don’t want to automate your customer communications entirely, but you can create communication templates that can save you (and your future team) time and energy. Head here for a list of templates to start with.

Six months and beyond

You’re growing and communicating and refining your processes, hooray! Now’s the time to think about scaling up. To do that you’ll want to…

  • Evaluate your hiring needs
  • Evaluate what’s working and what isn’t in your marketing strategy
  • Revisit your products, plans, and business model

Evaluate your hiring needs and weigh employees vs. contractors

One of the key decisions to make as your business grows is when to bring on help. There are a lot of sub-questions here:

  • What specific work to start outsourcing
  • Whether to use a contractor or virtual assistant , or hire someone full time (or part-time, but as an employee instead of a contractor)
  • How much work to offload at the moment

Step back and review what you most need at this stage: Is it a bit of help fielding customer service requests? Or are you ready to build out a more customized website than the WordPress theme you’ve been working from? Then, hire accordingly – in this case, customer service support or a web developer.

In general, contractors are less expensive than full-time employees and require less overhead and administrative work. However, they might be less reliable help than having a full-time employee. If you’re at a spot where you only need a few hours each week, or work on a project basis, hiring a contractor or freelancer is the way to go.

Evaluate what’s working and what isn’t, and try new strategies

This is a good time to look at your analytics and evaluate what you can or should change when it comes to your marketing. At about six months in, you should have enough data that you can start making smart data-based decisions. Here are some guides to help:

This is also a good time to try new things. If you haven’t experimented with PPC ads, that’s something to look into. And, if you’ve been using content marketing, you can start looking at leveraging your existing content more.

Revisit your products, plans, and business model

There might or might not be any changes to make here, but while you’re evaluating your other metrics, it’s a great time to review these, too. Here are some questions to ask yourself:

  • As my business has grown, is the base model of it sustainable? Am I finding myself working more hours than I’d like?
  • Are customers regularly asking for a product or plan that I haven’t created yet? Is there a reason not to create it?
  • Are there things I could add on to create more value (like a monthly group coaching call) that would be an easy upsell for customers?

Set the stage for success

No doubt about it, there’s a lot to accomplish when it comes to creating a subscription business. But if you follow these steps, keep working, and keep your eye on the prize — predictable (and sustainable!) recurring revenue — you’ll be rewarded.

Want to make it even easier? You can download the checklist as its own reference sheet for free below:

Six-Month Checklist

Enter your email below to receive your Six-Month Checklist for Subscription Success and subscribe to Rebilly updates: