Chip City Cookies, New York City’s fastest-growing cookie sensation, has taken a decisive step in its nationwide expansion by partnering with Square, the globally recognized restaurant technology platform from Block, Inc. With Square’s integrated tools, Chip City has streamlined operations across its business, giving both its customers and employees a seamless experience while ensuring the brand retains its signature charm and creativity.
What began in 2017 as a friendly neighborhood baking competition has transformed into one of the most beloved cookie brands in the United States. Chip City’s journey is proof that when entrepreneurial vision meets the right technology, growth can be scaled without sacrificing quality or guest experience.
From a Local Challenge to a National Sensation
Chip City was born when co-founders Peter Phillips and his friends decided to turn their passion for baking into something bigger. What started as a casual contest to see who could bake the best cookies quickly grew into a business when demand from friends, neighbors, and community members exploded. By 2017, Chip City had officially opened its doors in New York City, serving up freshly baked cookies in rotating flavors that quickly developed a cult following.
By 2020, the brand was poised for bigger things. That was also the year Chip City adopted Square’s technology to support its operational and customer service needs. This strategic move laid the groundwork for Chip City to expand from just five local stores into a powerhouse with more than 50 stores across nine states by 2025. And the growth shows no signs of slowing down.
Why Square Became the Backbone of Growth
Scaling a food business is no small feat, especially in the competitive dessert category. For Chip City, the challenge was how to grow quickly without losing the community-driven, high-quality feel that made the brand special. The solution was found in Square’s all-in-one restaurant platform, which gave the team the flexibility, data insights, and customer engagement tools needed to stay ahead.
“Delivering a great guest experience starts with smooth operations behind the scenes,” said Peter Phillips, CEO and Co-Founder of Chip City. “Square makes everything easier—training staff, managing menus, tracking performance—so we can focus our energy on the ideas that drive the brand forward, like new flavor drops, social moments, and creative marketing.”
Square’s ecosystem now powers nearly every aspect of Chip City’s operations. From point-of-sale transactions at the counter to labor management and back-of-house analytics, the platform has become the invisible but indispensable engine behind the cookie empire.
Seamless Experience for Customers and Staff
Across its network of stores, Chip City has implemented Square Register and Square Terminal for fast, secure order-taking and payment. This has significantly reduced wait times and improved accuracy, which is crucial for a high-volume, indulgence-driven brand like Chip City. The intuitive systems also make training new employees simpler, helping the company onboard staff quickly as it opens new locations.
On the backend, Square Dashboard delivers real-time insights into store performance across all locations. Managers and executives can track everything from daily sales to the popularity of specific cookie flavors. These insights go beyond operations—they influence product development, marketing strategies, and even decisions about where to open the next store. By staying data-driven, Chip City ensures its growth is strategic and sustainable.
Building Customer Loyalty, One Cookie at a Time
In addition to operational efficiency, Square has helped Chip City strengthen its relationship with customers. One of the most powerful tools in its arsenal is Square Loyalty, a rewards program that encourages repeat visits. Customers earn points with every purchase, which can be redeemed for future treats. This simple yet effective system has proven to be a game-changer for customer retention.
“We’ve had tremendous success with our Square Loyalty program, and our customers are repeat customers for the most part,” Phillips noted. “It’s been instrumental in building long-term relationships and ensuring that people don’t just come to us once—they keep coming back.”
For a brand like Chip City, where novelty and indulgence are key drivers, loyalty programs amplify the emotional connection with customers. Whether it’s returning for a classic chocolate chip or trying a limited-edition seasonal flavor, guests feel rewarded for their continued patronage.
Fueling Expansion with Technology and Investment
Chip City’s savvy use of Square technology has also made it more attractive to investors. By showcasing strong operational control and customer loyalty metrics, the company has successfully raised $17.5 million in venture capital from Danny Meyer’s Enlightened Hospitality Investments. This funding is earmarked to fuel further expansion, enabling Chip City to bring its cookies to even more neighborhoods across the United States.
The partnership between Chip City and Square is not just about technology—it’s about creating a scalable model that preserves the artistry and creativity that made the brand special in the first place. Each new store opening is backed by data insights, operational readiness, and a focus on delivering the same warmth and hospitality that customers experienced at the very first Chip City shop.
The Bigger Picture: Technology Meets Hospitality
Industry leaders have taken note of how Chip City is using Square to balance rapid growth with uncompromising quality. “Chip City shows what happens when a great brand pairs creativity with the right technology,” said Nick Molnar, Global Head of Sales and Marketing at Block, the parent company of Square and Cash App. “Square’s integrated restaurant platform is built for brands that want to grow without compromise—making it easier to scale rapidly while keeping the hospitality and flavor that keep customers coming back.”
This alignment between creativity and technology has positioned Chip City as a model for other fast-growing food brands. By embracing tools that enhance both the customer and employee experience, Chip City has demonstrated that scaling doesn’t have to mean diluting the brand’s identity. Instead, with the right foundation, growth can be a way to amplify what makes a brand beloved in the first place.
