Wineries and tasting rooms
More time making wine, less time in spreadsheets
The Monticello Wine Trail brings visitors to more than 40 wineries around Charlottesville all year. We help you turn that foot traffic into club members without adding admin to a small team.
Where the weekend goes
Reservations from five directions
Phone calls, emails, the web form, and walk-ins all want the same Saturday slots. Double bookings cost revenue and goodwill.
Inventory by memory
Cases move between the tasting room, club shipments, and wholesale accounts, tracked in notebooks and spreadsheets. You are usually guessing what is in stock.
Guests never hear from you again
Visitors loved the tasting. Club sign-ups and reorders depend on a follow-up that a small team cannot keep up with by hand.
Seasonal staff, seasonal retraining
More hands from spring through harvest, fewer in winter. Every cycle means retraining, and what people knew walks out the door.
A weekend in the tasting room
Composite of the small and mid-size wineries we have looked at on the Monticello Trail.
Now
- Staff field dozens of reservation calls each weekend
- Inventory checked by hand before each club shipment
- Thank-you emails go out weeks late, if at all
- Double bookings on peak Saturdays
- New seasonal hires take weeks to get up to speed
After
- Most reservations booked online with live capacity
- Case counts sync between tasting room and wholesale
- Thank-you and reorder notes go out the next day
- Capacity limits stop overbooking
- Written checklists cut onboarding to days
What we usually automate
Built on Tock, Square, Mailchimp, and whatever else you already pay for. No second software stack.
Tasting room bookings
Self-service scheduling with live capacity, automatic confirmations, and a waitlist.
Wine club
Shipment scheduling, preference tracking, and renewal reminders.
Inventory
Case-level counts across tasting room sales, wholesale, and online orders.
Guest follow-up
Post-visit thank-yous, event invitations, and seasonal offers based on what each guest bought.
Events
Private tastings, weddings, and vineyard dinners with timelines, vendor reminders, and guest lists.
Reviews
Review requests after visits, and drafted responses for you to approve.
Try it
A Saturday tasting, from the bar to the wine club
Nothing here is stored or sent anywhere. The steps are what the real systems do; the people and dates are made up.
Today the guest pays, says thanks, and drives off. The email on the card receipt goes nowhere. A club sign-up only happens if whoever is pouring remembers to ask while six other people wait. Reorders depend on the guest remembering the wine’s name two months later.
Connects Square (point of sale), Mailchimp, Wine club platform (Commerce7), Text messaging (Twilio)
What happens next will appear here, step by step.
One connected system for the whole winery
Everything connects to the systems you already run and handles the work that falls between them.
Post-visit follow-up
After a tasting, the system pulls purchase history from your point of sale and sends a thank-you with the wines they bought, within a day instead of weeks.
Inventory watch
Tracks case counts across tasting room, club, and wholesale. Alerts you when a varietal drops below your threshold, before you run out on a Saturday.
Reservation capacity
Watches bookings against your seating limits and flags the weekends that are filling up early so you can staff for them.
Wine club lifecycle
Renewal reminders, preference updates, and shipping notices go out on their own. Members who have gone quiet for 90 days get flagged so you can reach out personally.
Want a real look at your tasting room operation?
We will spend a Saturday on site if you want, or 30 minutes on a call. Either way you walk out with a short list of what is worth automating first.
Book a free discovery call