Smarter Staffing and Forecasting Decisions, Thanks To Square AI

Smarter Staffing and Forecasting Decisions, Thanks To Square AI
Square AI helps Vines & Rushes Winery manage the seasonality of its business by analyzing sales patterns to optimize dough preparation, staffing, and inventory.
by Ryan Prellwitz Dec 19, 2025 — 3 min read
Smarter Staffing and Forecasting Decisions, Thanks To Square AI

At Vines & Rushes Winery, what started as a family farm has grown into a community gathering place with wine tastings, woodfired pizza, and over 200 events each year. One aspect that challenges how we run things is that our business is seasonal — summer weekends can bring hundreds of guests, while winter weekdays are much slower.

That’s where Square AI comes in. It helps us analyze sales patterns and customer trends so we can make smarter decisions, like how much dough to ferment for our pizzas, how to schedule staff, and when to stock up on ingredients. With it, we’re able to serve our guests exactly what they want, when they want it. After eight years, we’ve nearly perfected the balance, keeping costs down and our customers happy year-round.

Using AI to create accurate staffing schedules

The dough is just one piece of our business. Running a restaurant, winery, and essentially an events space means knowing that there are peak times when we might need up to 14 people on staff all at once. There are also slow times where just one person will handle everything. It’s no surprise that staffing is a huge cost center – as it is for every business, really – and nailing it is a constant balancing act.

I’ve been part of the Square Beta Community for about 10 years now, which has been particularly exciting given my background in IT. Even before I worked with Square, I was always open to using tech to solve business challenges. Admittedly, I was curious but skeptical when Square first started developing Square AI. The AI boom was underway but hadn’t fully arrived yet. Square’s approach intrigued me because it would be using the actual data from my business, unlike commercial AI tools like ChatGPT. I really liked knowing that it was tailored to help me deeply understand my specific business.

I can construct the data exactly how I want to and need to see it with Square AI.”

Ryan Prellwitz Owner of Vines & Rushes Winery

Without that clarity, I could be paying people to stand around on a slow February afternoon or scrambling to cover a summer weekend.

Square AI helped me decode traffic patterns and forecast purchasing

I didn’t dig into my data as much as I should have before I started using Square AI. It wasn’t simple. I would look at reports and understand when we were busy, but pulling together information from multiple reports to answer nuanced questions took a lot of time. Time I didn’t usually have.

Our 48-hour fermentation for our pizza dough means that we need to be planning multiple days ahead for how much dough to make. If I get it wrong, I’m either tossing out expensive ingredients or using much less fermented dough in a pinch, which isn’t an optimal outcome for the kitchen or the customer. Square AI has transformed how I approach this forecasting. I’ve learned that the best way to predict how busy we’ll be on any given Friday or Saturday isn’t to look week-over-week, but rather look at that same Friday or Saturday from 52 weeks ago. The year-over-year comparisons are where the magic happens for ingredient planning.

With Square AI, I can ask specific questions and then take a minute to dig deeper. For upcoming weekends, I’ll look at what the pizza sales were like during that same weekend a year ago, then factor in other variables that might affect demand. For example, are we hosting an event that night? What’s the weather forecast? Is it a holiday weekend? While the numbers won’t necessarily be exact, this analysis helps me arrive at a solid estimate quickly and accurately. I can follow hunches and my intuition more easily. If it feels like margherita pizzas are trending up this season, for example, I can quickly confirm that with data and adjust my mozzarella order accordingly.

Data that’s actually useful and not overwhelming

There’s more information at my fingertips in a way that feels easy-to-use and intuitive, and I’m grateful for that. And AI generated reports are different from static reports because it makes it easier to access data and it actually engages your curiosity. One data result might pique my curiosity to ask more questions, and I’m able to follow those threads to new information.

As a business owner, that helps me get more creative with initiatives and solutions. Square AI specifically is helping me scratch an itch I didn’t know how to access before, and it’s improving how we run our business at Vines & Rushes.

Ryan Prellwitz
Ryan Prellwitz is the owner and winemaker at Vines & Rushes Winery in Ripon, Wisconsin. On his family’s multigenerational farm, he crafts award-winning cold-climate wines, serves locally sourced wood-fired brick-oven pizzas, and recently added an on-site coffee roastery. A former IT professional turned full-time vintner, Ryan brings a tech-savvy edge to every part of the operation while keeping warm, genuine hospitality at the heart of the guest experience.

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