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Seven emails that bring a customer back for a second order

The seven emails worth sending after a first order, when to send each, what the law asks of you, and how to do it by hand with no email tool.

10 October 2026 · The Workden team


Someone you have never heard of buys from your shop. You pack it, post it, and that is the last contact you have with them. Three months later you are paying for adverts to find new people while a list of past buyers sits in your store admin, untouched.

The short version: we suggest seven emails to a first-time customer, spread over the following months. Two of those emails are about the order, three are useful to them before they are useful to you, and only the last two ask for a sale. You can send all seven by hand from your normal mailbox if you take a few orders a day.

The seven emails, in order

The timings are a starting point from our own experience. Adjust them to what you sell.

  1. The order confirmation, with one useful line added. Sent straight away. Most shops leave this as a bare receipt. Add when it will be posted and one thing worth knowing before it arrives: how to store it, what size battery it takes, that the candle needs a two hour first burn.
  2. The "it is on its way" email. Sent when you post it, with the tracking link and the day it should arrive. This is the email that stops "where is my order" messages before they start.
  3. How to get the best from it. Three to five days after it arrives. Care instructions, a recipe, how other customers use it. No offer. The point is that they use the thing, because a product left in its box does not get reordered.
  4. The check-in. About two weeks after arrival. Ask one question, such as "did it fit?" or "how are you getting on with it?", and invite them to reply to you directly. Some will answer with a problem you can fix. Some will answer with praise, and you can ask those people for a review.
  5. What goes with it. Three to four weeks after arrival. This is the first email that sells. Recommend one or two things that belong with what they bought, and say why. A list of your bestsellers is not a recommendation.
  6. The "running low" reminder. Only if what you sell runs out. Mailchimp's guide to replenishment emails recommends reminding customers once a product is 70% consumed, so a 30 day supply gets a reminder around day 21. If what you sell does not run out, send "new since you last visited" at around two months.
  7. The "we have not seen you" email. Sent once the customer has been quiet for longer than your regulars usually go between orders. Klaviyo's help centre suggests setting this delay a little longer than your business's average buying cycle. Say what is new, and if you are going to offer money off, this is the place for it.

Two rules apply to the whole run. When a customer orders again, stop the run and start it from email one for the new order. And nobody should get email seven twice. If they stay quiet after it, leave them be.

Working out your own timings

Emails six and seven depend on how often your customers come back, and guessing is how shops end up emailing too early.

Take your last 20 customers who have ordered more than once. For each, count the days between their first and second order. The middle value of those 20 is your usual gap. Send the reminder a little before it and the "we have not seen you" email a little after it. A coffee roaster might land on four weeks and a furniture shop on eighteen months, and both are normal.

If you do not have 20 repeat customers yet, use the timings above and revisit them in six months.

What the law asks of you

Emails one and two are about an order the customer has placed. From email three onwards you are marketing, so the marketing rules apply.

In the UK, the ICO says you must not send marketing emails to individuals without specific consent, with a limited exception for your own previous customers, often called the soft opt-in. It covers an existing customer who bought a similar product from you, as long as you gave them a simple way to opt out when you first collected their details and in every message since. In practice that means an unticked "send me news and offers" choice, or a clear opt-out line, at checkout, and an unsubscribe link in every email from three onwards. If your checkout has never offered that choice, add it now and start the run with new customers only.

In the US, the FTC's CAN-SPAM guide says a commercial email must include your valid physical postal address and a clear explanation of how to opt out, and that you must honour an opt-out request within 10 business days. Messages that only confirm or complete a transaction the customer already agreed to are treated separately, which is another reason to keep the selling out of emails one and two.

This is a summary for shop owners and not legal advice.

Doing it by hand, for nothing

You do not need email software to start. If you take a handful of orders a day, this works:

  • Write the seven emails once and save them as templates or drafts in your normal mailbox.
  • Keep a sheet with one row per first-time customer: name, email, order date, what they bought, and a column for each email with the date it is due.
  • Once a week, sort by due date and send what is due. Change the first line of each so it mentions what they bought.
  • Keep a column for "asked to stop" and check it every time.

At that size it is a small weekly job, and the replies will teach you a lot about your customers. In our view it gets hard to keep up at around ten orders a day, or when a second person starts sending and neither of you knows what the other sent.

Before paying for anything, check the platform you already sell on. See whether your store already sends emails one and two, and look for where to edit their wording. If you are on Shopify, its help centre says you can create marketing automations to send emails to customers automatically, and that those go only to customers who are subscribed to marketing.

Where Workden fits

Workden is built for the point where the sheet stops working. Each customer has one page showing what they bought, what you last said to them and what they clicked. You can email a customer from Workden and it goes out as you, and whoever picks up next can see what was asked and what was promised. There is one list for the whole shop, with a nudge when something has gone quiet, which helps with emails four and seven, the two that tend to get forgotten. Newsletters are built by dragging blocks, sent to the people who asked for them, and you can see what each one earned.

One honest limit: email sequences that branch are still being built, so today the run above is a mix of your own sends and reminders, not a fully automatic sequence. It is £10.99 a month for your whole team, and there is a 14 day free trial if you want to try it with your own customers.

Questions shop owners ask

Do I have to offer a discount to get a second order?

No. Try the run without one first. A reminder at the right time and a relevant suggestion do a lot of the work. Keep money off for email seven, where the customer has already drifted.

Can I email everyone who has ever bought from me?

In the UK, only those who consented or who were given the chance to opt out when you collected their details, and only about similar products. If you are unsure whether older customers were given that choice, leave them out.