Principal Product Designer, Enterprise Menus

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

The Menu Management team defines the core experiences that shape how restaurants and hospitality sellers manage their menus across every channel. From POS to online ordering, these tools are the backbone of how sellers represent their offerings, maintain consistency across locations, and deliver seamless experiences for staff and diners alike.

We're looking for a Principal Designer with deep systems thinking, vision, and craft to shape the future of enterprise menu management and intelligent restaurant operations at scale. You'll partner with cross-functional leaders across Product, Engineering, Research, and Data Science to define strategic direction, drive cohesive design execution, and champion the seller experience.

As one of the most senior design leaders in this space, you'll set a high bar for ambition and craft, mentor other designers, and push the boundaries of what's possible with design and AI.

You Will

• Drive vision and strategy for the end-to-end menu management experience across Square's Food & Beverage platform, with a focus on multi-location, enterprise, and franchise operations.
• Shape data-driven interfaces that simplify complex workflows like bulk updates, menu versioning, and hierarchical permissions.
• Explore and integrate AI-assisted tools that help sellers create, optimize, and maintain menus across multiple channels and locations with greater speed, accuracy, and insight.
• Champion the seller experience, deeply understanding the operational complexity of multi-unit restaurants, franchises, and hospitality groups.
• Collaborate cross-functionally with Product, Engineering, Research, and Data Science to define roadmaps, align on priorities, and deliver impactful, high-quality design.
• Mentor and elevate designers across levels, fostering a culture of craft excellence, learning, and feedback.
• Contribute to shared systems, partnering with the broader Design Systems team to evolve menu-related patterns and reusable components that scale across surfaces and seller types.
• Measure and communicate impact, using qualitative and quantitative data to inform priorities and validate design decisions.

You Have

• 10–12+ years of product design experience, including leadership on complex, cross-functional initiatives in SaaS or platform environments.
• A portfolio demonstrating systemic thinking, deep UX craft, and examples of designing or integrating AI and automation into enterprise-scale workflows.
• Excellent storytelling skills, with a “show, don't tell” approach to aligning stakeholders through narrative and prototypes.
• Proven ability to shape long-term vision while driving near-term delivery.
• 3+ years of experience mentoring and developing other designers, with recognized influence across teams or organizations.
• Comfort navigating complex organizations, making informed tradeoffs, and iterating quickly toward clarity and outcomes.
• Curiosity and fortitude to challenge assumptions, explore new ways of working, and proactively uncover new opportunities for design.

Even better

• Familiarity with restaurant or hospitality operations, including menu complexity, modifiers, inventory dependencies, and compliance needs.
• Experience designing or prototyping with AI/ML systems, particularly natural language or recommendation interfaces.
• Experience shaping multi-year product roadmaps and influenc