How to Automate Club Caddie
Club Caddie emails invoices and charges members automatically on monthly, quarterly or annual cycles, and flags past-due balances to staff. For the follow-up, an AI agent such as WebRun drafts notes to members whose payment declined, win-back letters to lapsed members, replies to unanswered banquet inquiries and monthly statements for the office to read before they go.
Club Caddie keeps the member ledger beside the tee sheet
Behind every private or semi-private club sits a ledger of members: who pays dues monthly and who pays annually, who carries a food and beverage minimum, and who has cart privileges but not the pool. Club Caddie keeps that ledger next to the tee sheet. It is cloud-based management software for public, semi-private and country club golf operations, owned by Jonas Software, part of Constellation Software.
Charges from the golf shop register and the grill post to each member's account, and the Member Module emails the invoice and charges a stored card or ACH account on the member's own cycle. Members check their statements and receipts in the portal. Weddings, banquets, outings and leagues run through the event side of the same system.
The first of the month brings the declined cards
On the first of the month the invoices go out and the cards are charged. One member's card declines while the member is abroad for two weeks, and another's ACH payment comes back because the account was closed in the spring. The controller wants every large balance in view before the month's statements reach anyone.
A family who joined six years ago lets the membership lapse in July, and two months later nobody at the club has asked them back.
The catering office has a wedding inquiry for a Saturday in June sitting in the event module, still without a reply after two days, and the couple emailed two other venues the same night.
Club Caddie bills members automatically and flags past-due accounts to staff
Club Caddie's Member Module emails invoices and charges members automatically on monthly, quarterly or annual cycles, from cards and ACH accounts stored in a vaulted, PCI-compliant merchant system. Each membership class carries its own rules, and Member Flags show staff a note about a member, such as a past-due balance, whenever that member comes up.
The member portal keeps every statement and invoice since the member joined, itemized receipts and the balance against any minimum spend, and members can add a new card or ACH account there themselves. The Banquet & Event Management module holds the event calendar, deposits and payments, function sheets, contracts and a communication tracker, and the QuickBooks Sync App sends point-of-sale data on demand or as often as daily. SMS and email campaigns reach whatever groups of members the club builds.
A past-due flag reaches whoever opens that member, and the note to a member abroad is the controller's to write. A lapsed member hears from the club when someone builds a campaign for them, and an unanswered inquiry waits in the event module until the catering manager gets to it.
The controller works the declined payments the morning after
The controller sees every card or ACH payment that failed since yesterday morning, with the amount, the membership type and the failure reason where Club Caddie shows one. Each has a Gmail draft asking the member to update their payment details. Slack carries the count and the total outstanding.
On the first of the month, a club that wants statements read before they go reviews a draft for each active member, itemizing dues, pro shop and food and beverage charges with the closing balance, on top of the invoices Club Caddie emails itself. The Slack summary puts the members above the club's balance threshold first.
Every Monday the membership director goes through win-back drafts for members whose memberships lapsed 30 to 90 days ago and who have not rejoined, each naming their old membership type and how long they belonged, with a reason to come back. The events team sends a follow-up for every banquet or private event inquiry still unanswered in Club Caddie, each drafted with the event type and preferred date and an invitation to a site visit or a call.
Club Caddie's four jobs run daily, weekly and on the first of the month
The controller keeps every decision about money: retrying a card, refunding a charge or writing off a balance is no part of these four jobs. WebRun is an AI agent that works a real Chrome browser, signed in as you, and every one of these jobs starts on a Club Caddie screen and ends in a draft for the controller, the membership director or the events team to send.
The failed-payment and inquiry checks run at eight each morning, the win-back list on Mondays at nine and the statements on the first at seven.
Questions people ask
How long after a membership lapses does the win-back go out?
From day 30 to day 90 after it lapses, on the Monday run, provided the member has not rejoined or already had a win-back this cycle. Each draft names their old membership type and how long they belonged.
How does a member fix a declined payment?
In the member portal. The draft asks them to update their payment details, and members can add a new card or ACH account there without calling the club office.
Does the inquiry follow-up check our event calendar for open dates?
No. It drafts from the inquiry itself, using the contact, event type, preferred date, estimated guest count and any notes in Club Caddie's event section, and invites the couple or company to a site visit or a call, where the events team confirms the date.
Sources
- Member Management | Club Caddie Club Caddie's description of automatically emailed invoices and automatic billing on monthly, quarterly or annual cycles, membership classes with rules such as monthly minimums, and Membership Flags that alert staff to past-due balances.
- Banquet & Event Management | Club Caddie Covers the event calendar, deposits and payments, function sheets, the contract database and communication tracker, and the Golf Outing Manager that blocks the tee sheet.
- Accounting and Reports | Club Caddie Describes the QuickBooks Sync App, which syncs point-of-sale data on demand or on an automated schedule as often as every day.
- Club Caddie: Premier Golf Course Management Software States that Club Caddie is owned by Jonas Software, part of Constellation Software, and serves public, semi-private and country club operations, driving ranges and simulator businesses.
- Member Portal | Club Caddie Members see monthly statements and invoices back to when they joined, itemized receipts and balances against minimum spend requirements, and add credit cards or ACH accounts themselves.
4 ready-made Club Caddie workflows
Each one names the apps it touches and the exact steps it takes. Open one to read what it will do, then turn it on.
Want one of these running on your own Club Caddie?
Show WebRun the process once and it will run it on schedule, in your own private browser environment.

