Members: Transitioning From Annual to Monthly Memberships

When to Use This

Use this guide when your course has decided to stop selling annual memberships and move all members to a monthly billing model. The same approach works for any major class-type transition — quarterly to monthly, annual to seasonal, etc.

Before You Start

You’ll need:

Manager or Admin access in Club Caddie
A list of every active annual class assignment (export from Customers → Members)
The new monthly billing schedule decided (which day of the month dues post)
A plan for any pending mid-cycle members
A scheduled conversation with the Club Caddie membership team — the monthly billing job that runs your dues each month is inserted on the back end by Club Caddie support. You can configure the class, but the actual scheduled billing job needs to be turned on by the support team. Don’t skip this step.

Step-by-Step Instructions

Step 1: Stop new annual sales.

Take down the annual Sales Strategy link from your website and any marketing destinations. If you have multiple annual class types, replace each one’s link.

Step 2: Set expiration dates on every active annual class assignment.

If an annual class was created without an Expiration Date, the system will auto-renew it on the anniversary of the Effective Date. To prevent surprise renewals during the transition:

For each annual member:

Go to Customers → Members, double-click the member to open their profile.
Under the General tab, click Member Info.
Find the annual class assignment.
Under Action, click Expiration Date and set it to the last day of the corresponding month, one year after the Effective Date. (Example: Effective Date of May 12, 2025 → Expiration Date of May 31, 2026.)
Set the Bill Till Date to the same date.
Click Save.

For a bulk approach across many members at once, see the Members : Bulk Expiring Member Classes article — it covers the Excel export/import workflow.

Step 3: Configure the new monthly membership class.

Go to Settings → Class Management.
Create a new class or open the existing monthly class.
Set Due Type to Monthly and enter the Due Amount.
Toggle Prorate on Sale ON if you want online mid-month sign-ups auto-prorated. See Settings : Prorating Member Classes.
Save the class.
Generate the monthly Sales Strategy link and update your website and marketing destinations to point to it instead of the old annual link.

Step 4: Configure your global billing schedule.

Go to Settings → Membership Settings.
Set Monthly Billing Day to the day you want monthly dues to post each month.
Set the Bill Classes On Billed Till Date toggle based on your billing model:

OFF = members are charged at the start of each new cycle (the day after the Bill Till Date). Most courses use this — it means a member pays before they play.
ON = members are charged on the Bill Till Date itself (the last day of the prior cycle). Use this if you want statements sent on the 1st to already show the upcoming month’s dues.

Confirm Invoice Due After Days is filled in. This is what makes late fees fire on time.
Save the settings.

Step 5: Confirm the billing job is active.

Contact Club Caddie support and confirm your monthly billing job has been inserted on the back end. Without this, the schedule you just configured won’t actually run. Capture the date support confirmed the job is active in your implementation record so you have a reference if something looks off later.

Step 6: What happens at the natural transition.

When each annual class assignment hits its Expiration Date:

The class shows as expired in the member’s profile after that night’s billing run (changes take effect overnight, not in real time).
If that was the only class on the profile, the member account automatically converts from a Member to a regular Customer. History is preserved — they are not deleted.
If the member has already been assigned the new monthly class with a future Effective Date, monthly billing picks up from there.

Notes

The monthly billing job is inserted by Club Caddie support, not configured by you. This is the most common cause of “I set up monthly memberships and no one is getting billed” — the class is configured correctly, but the back-end job that runs the billing was never turned on.
Set the Expiration Date BEFORE the natural renewal date. A surprise auto-renewal on a $250 annual after the member thought they were on a $40/month plan is the worst-case scenario.
TIP: Online sign-ups with Prorate on Sale ON will see two charges close together — the prorated partial month at sign-up, then the first full month on the next billing day. Tell members at sign-up so they’re not surprised.
NOTE: Bill Till Date updates overnight, not in real time. If you check it the same day a charge ran, it may not reflect the new date until tomorrow morning.

Troubleshooting

Monthly dues aren’t charging after I configured everything.

Contact Club Caddie support. The class can be set up correctly while the back-end billing job is still inactive — they are two separate things. Support can confirm whether the job is running.

An annual member auto-renewed when I expected them to expire.

The class assignment is missing an Expiration Date. Open the member’s profile → General → Member Info → Action → Expiration Date and set it. Going forward, audit every annual class for missing expiration dates before you sign off on the transition.

The Tee Sheet still shows an expired member as active.

Expiration takes effect after the next overnight billing run, not immediately. Check again the next morning.