Staff Product Manager, Post-Checkout Experience

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
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Ordering directly from a restaurant or retail shop should be intuitive and feel dependable. Customers should know where their order is, hear about and easily follow updates, and get help quickly when something goes wrong.

We’re hiring a Product Manager to own that experience at Square, across food ordering and retail ecommerce. You’ll build customer experiences and seller tools for pickup, delivery, and shipping, helping businesses earn trust and bring customers back.

The problems are concrete: How do you follow an order’s progress? What should happen when a delivery runs late or an item goes missing? How do you make a refund clear, or give a seller an easy way to make things right? You’ll own the experience from the moment an order is placed through its arrival and any help needed afterward.

We’re looking for someone with a strong product sense who notices where people get confused, knows when to simplify, and cares about the details that build confidence. You’ll spend time with customers and sellers, work closely with design and engineering, and turn those insights into products that customers trust and repeatedly come back to for their next purchase.

You Will
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• •Own the strategy and priorities. Set the direction for Square’s post-checkout customer experience across food ordering and retail. Use customer needs and business goals to decide which problems matter most, where to invest, and what can wait.
• •Bring the work together. At Block, engineers and people across teams also lead individual product improvements. You will connect those efforts across Square and external partners, spot gaps, resolve competing priorities, and make sure the pieces form a clear, consistent customer experience as more people prototype and ship.
• •Design and define user experiences. Work closely with design and engineering to shape key customer journeys, from tracking an order to getting help when something goes wrong. Bring personal taste and attention to detail to the flows, interactions, and communications that build trust.
• •Help the team scale through automation. Use AI and other tools to connect and automate repeatable work across customer research, analysis, prototyping, product development, and launch. Build reusable workflows, share what works, and give teams the context and tools to make good decisions independently.
• •Set the quality bar and guide important decisions. Define what good looks like and evaluate product ideas and AI-generated work against real customer scenarios. Test assumptions, give specific feedback, and keep refining until the experience is useful, clear, and dependable. Decide where AI and automation improve the experience and where human judgment matters.
• •Prototype and ship improvements yourself. Use AI tools to turn ideas into working prototypes, test them with customers, and learn quickly. Use GitHub and other developer tools to contribute changes through pull requests and work with engineers to ship improvements to production.
• •Own the outcomes. Follow work through launch and use customer feedback and data to guide improvements. Measure whether customers feel informed, get problems resolved quickly, and choose to order again, using signals like order-status inquiries, resolution time, satisfaction, and repeat purchases.

You Have
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• •6+ years of product management experience.
• •Consumer product judgment. You’ve shipped customer-facing products at scale that make complicated things feel simple. You can explain your decisions and what you learned from customer behavior.
• •Hands-on building with AI. You use AI to build working