Friday, September 5, 2025

Chip City Cookies Thrives with Square’s Innovative Restaurant Solutions

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New York’s beloved cookie brand, Chip City Cookies, is on a path of remarkable growth, having rapidly expanded its presence from five original locations to over 50 in just a few years. The key to their success lies in a strategic partnership with Square, the all-in-one restaurant platform that powers their operations and enables their rapid scaling.

Founded in 2017 from a friendly baking competition, Chip City has become a national sensation, spreading its innovative flavors across nine states. The decision to adopt Square’s technology stack in 2020 has been pivotal for the brand, providing the essential tools necessary for managing everything from customer interactions to detailed back-of-house analytics. This integration has been crucial for maintaining efficiency and preserving the quality experience that customers have come to love.

Peter Phillips, CEO and Co-Founder of Chip City, emphasizes the importance of seamless operations. “At Chip City, delivering a great guest experience starts with smooth operations behind the scenes,” Phillips states. “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.”

For small business owners, adopting a robust system like Square can significantly enhance operational efficiency. The tools used by Chip City, such as Square Register and Square Terminal, streamline order-taking and payment processes, ensuring swift service for both staff and customers. Additionally, the Square Dashboard provides real-time performance insights across locations, allowing businesses to adjust strategies based on actual data. This capability can aid small businesses in quickly responding to market demands and optimizing their offerings from operational hours to product selection.

Another noteworthy aspect of Chip City’s approach is its investment in customer loyalty through technology. By leveraging Square Loyalty, every cookie purchase allows customers to earn points toward rewards. This strategy has proven effective, transforming many first-time visitors into loyal patrons. Phillips noted, “We’ve had tremendous success with our Square Loyalty program, and our customers are repeat customers for the most part.” Such loyalty programs can be especially beneficial for small businesses aiming to cultivate long-term customer relationships.

Chip City’s tech-savvy approach has also attracted significant investment, raising $17.5 million in venture capital from renowned investor Danny Meyer’s Enlightened Hospitality. This level of funding facilitates ongoing expansion efforts while enabling the company to innovate continuously. For small business owners, securing funding often hinges on demonstrating not just a viable product or service, but also a scalable operational model using effective technology.

However, it’s essential for small businesses to recognize some potential challenges when implementing an integrated system like Square. The initial setup and learning curve for staff can be demanding. Additionally, while these technologies can drive growth, they also require oversight to ensure that the customer experience remains personal and engaging. Maintaining the human touch amid increasing automation should be a priority for any business.

Nick Molnar, Global Head of Sales and Marketing at Block, highlighted the blend of creativity and technology for business success. “Chip City shows what happens when a great brand pairs creativity with the right technology,” Molnar said. “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.”

As Chip City continues to innovate and expand, other small business owners can glean valuable insights from their experience. Embracing technology not only streamlines operations but also enhances customer engagement. The integration of loyalty programs and real-time analytics is crucial for staying competitive in today’s fast-paced business environment.

To learn more about Chip City Cookies and their journey, or to find a location near you, visit Chip City Cookies. For further information on Square’s offerings for food and beverage businesses, explore Square for Restaurants.

For additional details about the technology that supports Chip City and other businesses, visit the original press release here.

Image Via BizSugar

Elizabeth White
Elizabeth White
Elizabeth White is a retail strategist and writer specializing in small business success. With over a decade of experience in retail management and merchandising, Elizabeth has helped countless entrepreneurs optimize their store layouts, improve inventory management, and boost customer engagement. Her insights cover everything from in-store marketing tactics to e-commerce integration. Elizabeth’s practical advice empowers small business retailers to thrive in competitive markets. When she's not exploring retail trends, Elizabeth enjoys visiting local boutiques and curating her ever-growing book collection.

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