If you run a membership, you may have a group of members who've paid you month after month for a long time. They show up, they use what's inside and they keep renewing. But every one of those members is still one card problem or one busy month away from canceling and you're collecting their money in small pieces when some of them might choose to pay for the whole year if you gave them that option.
That's what an upgrade sequence is for. It's a short set of emails that goes to your monthly members at the right moment and offers them a better deal to switch to an annual plan or a lifetime plan. It runs on its own once it's set up, so it's one of the ideas on my Sales on Repeat list of 99 ways to make sales every day, under the ideas for what happens after the sale.
In this post I'll walk you through how to price the annual and lifetime options, when to send the sequence, what to write in each email and how to set up the checkout so nobody gets charged twice.
Why the upgrade is worth setting up
When a monthly member moves to annual, you get a full year of payments at once and they stop having to decide every month whether to stay. When a member moves to lifetime, you get one larger payment and they never have to think about renewing again. Both are good for the member too, because they pay less overall than they would month by month.
The upgrade also gives your membership a second way to make money from people who already said yes. This works with the members you already have, as long as they hear about a better option at a time when it makes sense for them.
And because the sequence is automated, it sells on a regular basis without a launch. Every week, some of your monthly members hit the point where the sequence starts, so the offer goes out on its own all year.
Price the annual and lifetime plans before you write anything
Start with the numbers, since the emails are built around the offer. You need three prices that make sense next to each other: the monthly price, the annual price and the lifetime price.
The annual price
A simple way to set the annual price is to charge ten months and give two months free. If your membership is $29 a month, that's $348 for twelve months on the monthly plan, so an annual plan at $290 saves the member $58. That's easy to explain in one sentence and the member can do the math in their head.
The lifetime price
Lifetime is harder to price because you're selling access with no end date. One way to start is to price it at about two to three years of the monthly price. For a $29 a month membership, that puts lifetime somewhere between about $697 and $997. Pick a number you'd still feel good about if a member stayed for ten years and used everything.
Before you offer lifetime, write down what it covers. Does it include new courses you add later? Live calls? Any higher tier you might build? Put that in writing on the checkout page and in the emails, so there's no confusion a few years from now.
The upgrade price
You can offer the upgrade at your regular annual and lifetime prices, or you can give monthly members a special price that's only available inside the sequence. If you give a special price, put it on its own private checkout page that's only linked from these emails. That keeps your public prices the same for everyone else, which is the same idea behind taking permanent discount codes off your public pages.
Another way to sweeten the offer is to credit what they've already paid this month toward the upgrade. That way nobody feels like they're paying for the same month twice.
When to send the upgrade sequence
Timing matters a lot here. If you send the upgrade to someone who joined last week, they haven't seen enough of the membership to commit to a year. If you wait too long, you've missed people who would have upgraded and then canceled first.
Here are a few good starting points and you can pick one or use more than one:
- After the third payment. Someone who has paid you three times has decided the membership is worth keeping, so they're a good fit for a longer plan.
- On their membership anniversary. Six months or one year in is a natural moment to say thank you and offer a better deal.
- After a win. If members finish a challenge, complete a course or post a result in your community, that's a moment when they feel good about being there.
- Before a price increase. If you're raising the monthly price, monthly members can switch to annual or lifetime at today's price before the new one starts.
The easiest one to automate is the payment count. Most checkout and email tools can tag a member after a certain number of payments, or you can start the sequence a set number of days after they join. If someone joins and you use a 90 day delay, they'll get the sequence right around their third payment.
What to write in each email
The sequence can be short. Four emails over about a week is plenty and each one has a job. Here's a version you can follow.
Thank them and show what they've used
Open by thanking them for being a member and name a few things inside the membership they've had access to so far. Then tell them there's a way to keep all of it for less and introduce the annual and lifetime options with the prices and the savings.
Do the math for them
Write out what they'll pay over a year on monthly and what they'll pay on annual. Then do the same for lifetime over two or three years. Keep it to plain numbers so they can see the difference without opening a calculator.
Answer the questions they'll have
Cover what happens to their monthly plan when they switch, whether they lose anything, what lifetime includes and what happens if the membership changes. These are the things that make people hesitate, so answer them plainly.
Close the window
If you're offering a special upgrade price, tell them this is the last day it's available and when it ends for them. Keep it short, repeat the prices and give the link one more time.
A few things to keep in all four emails. Use one link per email that goes straight to the upgrade checkout. Write the prices as numbers. And keep the tone friendly, because these are people who already pay you every month and you're offering them a better deal.
A real deadline for each person
If the upgrade price is special, the deadline has to be real. The window starts when each member enters the sequence and closes a few days later, so everyone gets the same amount of time no matter when they joined. After the window closes, the private checkout should stop offering that price to them and the regular annual and lifetime prices are still there on your normal pricing page.
Because this is an evergreen sequence, don't put a calendar date or a day of the week in any of the emails. People enter it on different days all year, so say something like "this offer ends in two days."
Set up the checkout so nobody gets charged twice
This part takes the most care, so take your time with it. When a monthly member buys the annual or lifetime plan, their monthly subscription has to stop. If it doesn't, they'll keep getting billed every month on top of what they just paid.
Before you turn the sequence on, buy the upgrade yourself with a test account that's on the monthly plan. Then check that the monthly subscription was canceled, the new plan shows up and the member still has access to everything. If your tools can't cancel the old plan on their own, set a reminder to cancel it by hand for every upgrade until you can automate it.
Here's what to set up:
- Make a separate checkout for each upgrade. One for annual and one for lifetime. If you're using a special upgrade price, these are private pages that only get linked from the sequence.
- Connect the checkout to your membership. When someone buys, they should keep the same login and the same access, just on the new plan.
- Cancel the monthly plan. Some checkout tools can cancel the old subscription when the new one is bought. If yours can't, cancel it by hand the same day.
- Tag the member in your email tool. Add an "annual" or "lifetime" tag and remove the "monthly" tag, so they stop getting the upgrade sequence and start getting the emails that fit their new plan.
- Send a short confirmation email. Tell them the upgrade worked, what they paid, that the monthly plan has stopped and what lifetime or annual includes.
Mistakes to avoid
Most of the problems with upgrade sequences come from a handful of setup mistakes. Here's what to watch for.
- Sending it to brand new members. Give people time to use the membership before you ask for a bigger commitment.
- Sending it to members whose card just failed. If someone is in your failed payment emails, wait on the upgrade until their payment is sorted out. Two sets of payment emails at once is confusing.
- Pricing lifetime too low. Lifetime members use the membership for years and never pay again, so make sure the price makes sense for how long they might stay.
- Not saying what lifetime covers. Write it down on the checkout page so it's clear years from now.
- Forgetting to cancel the monthly plan. Test it before you go live.
- Leaving annual members in the sequence. Make sure the sequence only goes to people tagged as monthly and that they leave it the moment they upgrade.
- Putting the special price on your public sales page. Keep it on the private checkout so it stays a reason to act inside the window.
"Every week, some of your monthly members hit the point where the sequence starts, so the offer goes out on its own all year."
Dr. Destini CoppA hypothetical example
These numbers are made up to show how the math works. They aren't results from my business or anyone else's.
Say you run a membership for knitters at $29 a month and you have 200 monthly members. You set the annual plan at $290 and the lifetime plan at $697 and inside the upgrade sequence you give monthly members a special annual price of $249 that's only on the private checkout.
You set the sequence to start 90 days after someone joins, so it reaches people around their third payment. Each week a handful of members enter it. Email one thanks them and names the pattern library, the monthly live knit-along and the stitch help videos. Email two shows that twelve months on monthly is $348 and annual in the sequence is $249. Email three answers questions about keeping their login and what lifetime includes. Email four says the $249 price ends tomorrow.
Now say 10 of those members choose annual at $249 over a few months. That's $2,490 collected upfront and those 10 people won't see a monthly renewal for a full year. If 3 more choose lifetime at $697, that's another $2,091. Again, those are made-up numbers, but they show how a few upgrades turn small monthly payments into larger ones without bringing in a single new member.
How this fits with the rest of your membership funnel
Your funnel is the path people take from first hearing about you to buying from you. The upgrade sequence works best when you already have steady monthly members coming in. If you're still building that part, start with making your membership the upsell on every product. An upsell is the next thing you offer right after someone buys and that spot is where a lot of new monthly members can come from. A free community with a paid upgrade is another way to bring people into the monthly plan in the first place.
Once monthly members are coming in, the upgrade sequence is the next step in the path. Someone buys a small product, joins the monthly plan and then gets the chance to move to annual or lifetime after they've been around long enough to know it's worth it.
Wrapping up
An upgrade sequence is four emails, two checkout pages and a few tags in your email tool. Price the annual and lifetime plans first, pick when the sequence starts, write the emails so the math is easy to see and test the checkout so the monthly plan stops when someone upgrades.
If you're not sure whether this is the right idea to set up first, I made a free Sales on Repeat skill for Claude that asks a few questions about your business and picks the first three ideas you should start with. And you can see all 99 ideas in the full Sales on Repeat list.
Find your first three Sales on Repeat ideas
The free Sales on Repeat skill is a Claude skill that asks a few questions about your business and picks the first three ideas you should set up.
Get the free Sales on Repeat skill →Frequently asked.
How do I get monthly members to switch to an annual plan?
Send a short email sequence to monthly members after they've been around for a few months, like after their third payment. Show the yearly total on monthly next to the annual price so the savings are easy to see and link to a checkout for the annual plan. Make sure the monthly plan stops when they upgrade.
How should I price a lifetime membership?
One way to start is about two to three years of the monthly price. Pick a number you'd still feel good about if the member stayed for ten years. Write down exactly what lifetime includes so it's clear years from now.
When should I send a membership upgrade offer?
Good times are after a member's third payment, on their six month or one year anniversary, after they finish something inside the membership or before a price increase. The payment count or a set number of days after joining is the easiest to automate.
Should I give monthly members a special upgrade price?
You can. If you do, put the special price on its own private checkout that's only linked from the upgrade emails and give each person a real deadline counted from when they started the sequence. Your public prices stay the same for everyone else.
How do I stop a monthly member from being charged twice after upgrading?
Set up your checkout so the monthly subscription is canceled when the annual or lifetime plan is bought. If your tools can't do that on their own, cancel it by hand the same day. Test it with your own account before you turn the sequence on.
Dr. Destini Copp helps digital product creators build sustainable, systems-based businesses through the Creator Growth Flywheel framework. She's the founder of Creator's MBA and HobbyScool, and has been teaching online business strategy for over a decade. Learn more →
