Principal Product Designer, Retail

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 Retail, Catalog, and Inventory team designs the core experiences that power how sellers run and grow their businesses. From the smallest shop to larger-scale operations, these tools are the backbone of how all Square merchants manage products, track stock, and deliver seamless buying experiences across every channel. This team ensures Square’s ecosystem is not only intuitive and reliable but also transformative—helping sellers reduce complexity, operate more efficiently, and unlock new opportunities for growth.

We’re looking for a Principal Designer with strong systems-thinking, vision, and craft to shape the future of retail businesses. You’ll partner with cross-functional leaders and teams across Square to define strategic direction, guide design execution across multiple surfaces, and champion the voice of the seller. 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. 

You Will

• Collaborate with Designers, Product Managers, Engineers, and Data Scientists to shape a vision and roadmap that up-levels the quality of the product experience for our customers


• Propose design and product opportunities, promote them across the organization, and own projects from concept through release


• Promote design excellence through mentorship, feedback, and knowledge sharing


• Maintain a principled, customer-centric approach throughout each project, using data, insights, and experience to inform decisions


• Experiment with new design tools, methodologies, and approaches to improve the design process and inspire creativity


• Foster a culture of experimentation and creativity, and build connections across teams and disciplines

You Have

• 12+ years of relevant Product design experience


• A portfolio demonstrating exceptional UX craft, vision, systems design, and prototyping skills


• Experience as an influential design leader who ships impactful, strategic work—including multi-year visions to iterative releases


• Strong design point of view and understanding of how to balance the needs of the customer with that of the business


• Excellent storytelling skills, and a 'show don't tell' approach to aligning teams around a shared vision, often through prototyping and AI tools


• A strong drive to continuously learn and grow, particularly in leveraging AI and emerging technologies to enhance workflow efficiency and optimize team processes

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.

While there is no specific deadline to apply for this role, U.S. roles are typically open for an average of 55 days before being filled by a successful candidate. Please refer to the date listed at the top of this job page for when this role was first posted.