Staff Product Manager, Post-Checkout Experience

Square; San Francisco (CA); On-site; USD 198,000 - 297,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement plans

Job summary

Square is hiring a Product Manager to own the post-checkout experience for food ordering and retail. You’ll build customer experiences and seller tools for pickup, delivery, and shipping to earn customer trust and drive repeat purchases.

You will work closely with design and engineering, turning insights from customers and sellers into practical products, with a strong emphasis on AI-driven automation and end-to-end ownership of the journey.

Qualifications

• 6+ years of product management experience.
• Shipped customer-facing products at scale that simplify complex problems.
• Hands-on building with AI to prototype and test ideas.
• You bring taste and craft, and a high bar for quality.
• You set strategy and priorities, and explain trade-offs clearly.
• You use customer research and data to guide decisions, even when data is incomplete.
• You lead across teams and align them around a clear direction.
• Experience with consumer products, ecommerce, marketplaces, or customer support is a plus.

Responsibilities

• Own the strategy and priorities for post-checkout customer experience across food ordering and retail.
• Connect efforts across Square and external partners to create a seamless, consistent experience.
• Define key customer journeys from order tracking to help when issues arise and refunds.
• Collaborate with design and engineering to shape flows and interactions with attention to detail.
• Lead automation initiatives using AI to streamline research, prototyping, and launch processes.
• Set quality standards and evaluate ideas against real customer scenarios, refining where needed.
• Prototype and ship improvements using AI and developer tools like GitHub.

Skills

Product management

AI prototyping

Customer research

Strategic prioritization

Cross-functional leadership

Analytical judgment

Design collaboration

Consumer product sense

Tools

GitHub

Job description

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

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

• 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

• 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 prototypes, automate recurring work, and test ideas. You can use GitHub and other tools to make a change and submit a PR. You can show what you’ve built and what you learned.
• Taste and craft. You work closely with design and bring personal taste and a high bar for quality. You recognize generic or weak output, give specific feedback, and iterate until the experience feels thoughtful and useful.
• Strategy and prioritization. You’ve set product direction and turned it into clear priorities. You make thoughtful tradeoffs and can explain what deserves investment and what can wait.
• Customer research and analytical judgment. You use customer conversations, research, and behavioral data to guide decisions. You’re comfortable moving forward when the problem is ambiguous or the data is incomplete.
• Leadership across teams. You bring people together around a clear direction, resolve disagreements, and get work shipped. You give others the context to make good decisions and keep moving.
• Relevant experience. Experience with consumer products, ecommerce, marketplaces, or customer support is a plus, but not required. You’re curious about how businesses operate and what makes customers trust them.

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.

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.

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

To find a location’s zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information.

• Zone A: $198,000 — $297,000 USD
• Zone B: $188,100 — $282,100 USD
• Zone C: $178,200 — $267,400 USD
• Zone D: $168,300 — $252,500 USD

Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self‑custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

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