Rebilling and Shipping: A Best Practice Guide

Rebilling and shipping are two critical touch points you make with your customers each month. Master your monthly schedule with this best practice guide.

As a subscription business, you make two critical touch points with your customers every month: the delivery of your product and rebilling subscriptions. Both can significantly impact customer service load and customer retention. What’s more, both play important roles in scheduling internal business practices like product procurement and payroll.

Let’s explore the details of these two important dates, and discuss a few simple best practices that can help you master your monthly schedule.

Part 1: Shipping

Shipping is one of the most exciting times of the month. Your customers are set to receive their subscription and provide feedback on all of the hard work you’ve done curating and putting together the current month’s box.

But when do you ship? Do you ship every day you get an order? Once a week? Twice a month?

Deciding Frequency

Instead, it is highly recommended that you ship once a month, especially in your early stages. By shipping once a month, you solve several problems:

  • Customer Expectations: A single, clear shipping date is easy to remember. In addition, once you’ve set a clear precedent that shipping happens only once a month, you won’t have to worry about complaints in regards to shipping frequency (a common misconception).
  • Easier to Interpret Data: By removing ‘time of month’ as a variable in your customer experience, you simplify analysis. In other words, if all your customers have the same delivery experience every month, you can remove that as a factor when trying to understand changes in churn and other subscription KPIs.
  • A Deadline for Curation: Your shipping deadline also serves as a deadline for product procurement. A normalized schedule makes for easier purchasing and ensures you’re never using cash you don’t have or using credit to purchase product.
  • Easier Fulfillment: You’ll always pack (or, preferably, schedule your packing) the same week each month. This will also most likely reduce your fulfillment costs as you won’t ever be paying to store product. See our guide on ‘Fulfillment – Outsourcing Vs. In-House’.

Choosing the Date

When choosing your date to ship, I recommend choosing a date in the 2nd or 3rd week of the month. For example, the 10th, 15th or 20th. There are several good reasons to choose a date in that time frame:

  • Clearly associate the shipped box to the month. For example, boxes that ship on October 15th and arrive around the 20th clearly are the ‘October’ boxes. Shipping later in the month and having boxes arrive the following month can be confusing for customers.
  • Fewer Holidays: Some of the largest national holidays, including Christmas, Thanksgiving, Labor Day, etc, occur during the first and last weeks of the month. Avoiding these means you can avoid thinking about how shipping and fulfillment will be affected.
  • Works well with rebilling: Read on to the next section to find out why!

Shipping Best Practices

Once you have your schedule determined, there are a handful of other best practices you should follow:

  • Make sure tracking emails are functioning correctly, are updated, and are properly scheduled
  • Announce shipping to your community via social networks, build engagement by asking questions and sharing photos
  • If there are significant changes in your schedule, like a delay due to a storm, communicate it clearly to your customers. Remember, you’ve set an expectation by choosing a date.
  • Notify customer support. This is the eve of an uptick in requests, so make sure your team is prepared.

Part 2: Rebilling

After you’ve sent your subscribers their box, the next big date on the horizon is rebilling. By now, customers have unboxed, shared, tweeted, and video blogged about your box. You’ve likely processed many of the churned customers after delivery, but there’s always the tendency for customers to “forget they had a subscription,” leaving them shocked with a charge on their statement.

Choosing the Date

A lot of thought has gone into when you should rebill your customers. Rather than get into the specifics on the time of day and day of week of rebilling in this guide (covered here), let’s discuss it in terms of you larger schedule.

It’s generally advised you rebill along these following lines:

  • Never before your customers have received that month’s box
  • Never more than a week or so after they’ve received their box. The experience is fresh in mind, and they’re more likely to remember why they enrolled in the expense.
  • Always around the same time each month. Sporadic billing dates can be confusing.
  • Not on a rolling basis (ie, if you signed up on the 6th, you’re rebilled on the 6th every month). This causes lumpy financials and makes it harder to plan effectively.

That considered, if you follow the date suggestions for shipping, you might consider scheduling rebilling on the 18th, 23rd, or 30th of each month (about a week, including two days for weekends, after shipping).

Rebilling Best Practices

Once you have your date decided, follow these best practices to keep rebilling headache free:

  • Communicate it to your customers! Set the expectation.
  • Use reminder emails only when needed. By reminding people of their subscription, you may increase churn unnecessarily. Reminding customers when you need to, ie. a rebilling date change, price change, etc.

Put Shipping and Rebilling to Work for You

Effectively planning ahead and setting normalized schedules for these two important times of the month can greatly improve experience, both for customers and for you as the business owner.

Jameson’s Suggested Shipping & ReBilling schedule

  • Ship on the 20th of the month
  • Re-Billing on 30th of month*

*Depending on the shipping method you use, allow at least 2-4 days for shipping + 2-4 days to give customers a chance to cancel BEFORE rebilling happens.

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About Jameson Morris

Jameson Morris is an entrepreneur and pioneer of Subscription Commerce. As a self proclaimed 'subscription box serial entrepreneur,’ Jameson has founded multiple successful subscription businesses, such as Conscious Box, Escape Monthly and Yogi Surprise.

20 Responses

  1. Amber Golightly

    “Deadline for Curation” is much more eloquent than what I’ve been saying, “Do this thing by this day or you FAIL!” I have 3 deadlines. One for a brand/company’s product commitment, one for procurement and then shipping (12th). All about a week apart. Ideally, ex: a Nov brand will have committed in Sept-Oct (if not way earlier), fulfilled the order for inventory 2 weeks prior to shipping (1st-5th), then boxing the first weekend of the month, then shipping (the 12th). The biggest issue I have come across, is that I am growing to quickly for a small company or artisan to fulfill the demand of the month they committed to. They commit while I am at X number of subs, by the time I’m placing the order it’s gone up 30%. Curating closer to the shipping date is a bit scary for numerous reasons. I also don’t want to prep a maker with false excitement that they are going to load off a ton of inventory by warning them the number could increase significantly.
    Any tips? 🙂

  2. Kim

    Great advice Jameson!

    I have a question about shipping and rebelling. What if I want to ship to customer twice a month and rebill once a month? I am thinking how to choose proper dates for this. Any advice?

  3. mario

    i dont get why you would bill after you have sent them the product, what if they get the product and havent been billed yet and then cancel the order?

    1. Hey Mario,

      You always bill in advance – however, when you immediately rebill after they receive the product, customers are more likely to remember the good product experience and not cancel. So the order is: Sign up — > Receive Order — > Renew — > Receive New Order — > Etc.

      Hope that’s clear!

  4. Amy Hostelley

    What if I want to ship to customers twice a month and rebill once a month? I’ve been trying to think of the best way to handle this and would welcome your thoughts.

    1. Hi Amy,

      When you renew someone, it creates an order to fulfill in Cratejoy. In order to do 1 rebill and 2 shipments, you’d need to somehow manually create other orders or keep track of that (maybe download your shipment list, then save 2 copies with dates dictating the time you’re supposed to print labels).

      What’s the product concept?


  5. Danny Taing

    I heard from a CPA friend that there might be some legal issues with recurring billing so far in advance of the actual ship date of the product (i.e., ship out on 10th but bill on 20th of month before). Do you know of a law that says one has to bill within 5 days or a week before shipping out the product? Thanks!

    1. Hi Danny. I’m not familiar with that law and I’m skeptical that it exists considering the enormous amount of businesses that charge people far in advance for products. I also haven’t heard of anyone having problems with it before.

      It really comes down to communication – if your customers know the box ships on a specific date & they rebill on a specific date, it shouldn’t be a problem.


    1. Hey Tori,

      It might be a funky UX, because checkout/account pages would all be on Cratejoy, but I can definitely envision a solution that would allow that. You’d need to embed all links on the checkout/account pages to direct to your current site, so when they click out of those areas they don’t find themselves in your would-be CJ site.

      I’d try to see how much of your current site you could migrate over first!

      Hope that helps,

  6. Dean

    Hi Jesse,
    I understand the reasons for wanting to ship once a month, your article is very clear on this.

    I have a slight issue with the concept of a customer missing (let’s say by a day) a deadline for shipping that month’s subscription, they will then have paid for something and have to wait nearly a month to receive anything. This isn’t great for a new customer.

    Wouldn’t it be better to ship existing customers on the same day of the month and new customers have a couple of shipment dates during the last couple of weeks of the month?


    1. Hey Dean,

      It depends on how your business is set up. If you have a welcome box you can dedicate to all new subscribers, the paradigm you explained can work. I’ve found that as long as you’re clear, most people don’t mind waiting. And you also have flexibility – if 20 people sign up a day after your cut off, you *could* always immediately ship them a box then renew them at the next renewal date – as long as you make it clear to them that they were included in the window.

      Let me know if that answers your question!

  7. Ashley

    Any advice for the suggested cadence of shipping and rebilling dates if you’re a bi-monthly box? I’m contemplating shipping on the 15th of the first month (Sept 15 for the Sept/Oct box) and rebilling in late October for the Nov/Dec box. Do you have any best practices or learnings from boxes who are similarly scheduled?

  8. Aparna Pande

    Is there a best practice on how far in advance of a rebilling date that a “reminder” email should be sent out? And, is this reminder email typically sent for monthly, 3 month, and 6 month renewal terms or only the longer terms (only 6 month, or only 3 and 6 months)?

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