Senior Product Manager, Retention

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
Square succeeds when our sellers stay with us and grow over time. The Retention team ensures we deepen usage across our ecosystem, support at-risk sellers, and increase the lifetime value of Square users. As Product Lead, Retention, you will define and deliver the product strategy to improve seller retention across all segments—from micro-sellers to fast-growing SMBs. You will identify points of friction, build proactive expand or save experiences, and partner cross-functionally to ensure sellers have compelling reasons to stay and grow with Square. This is a senior, high-leverage role with deep ownership over seller happiness, churn reduction, reactivation, and loyalty-driving experiences. You’ll work with Product, Engineering, Design, Data, Support, Sales, and Marketing to uncover churn signals, scale re-engagement tactics, and drive retention improvements at scale.

You Will

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  • Build and Execute the Retention Strategy
    
    
    
    • Own the roadmap for reducing voluntary and involuntary churn.
    
    
    • Launch proactive save flows and winback strategies based on predictive signals.
    
    
    • Create segmentation-driven retention journeys across seller types and lifecycle stages.
    
    
  
  
  • Improve Product-Led Retention Levers
    
    
    
    • Identify and remove friction points that lead to seller churn such as when a business is adapting to changing business conditions, exploring multichannel, engaging more staff members, scaling locations, or seeking to accomplish more advanced workflows with Square.
    
    
    • Build experiences that reinforce product value after major milestones (e.g., onboarding, 1st hardware purchase, 30-day inactivity) and especially increase 1st year payments retention.
    
    
    • Partner with Support, AMs, and GTM to ensure high-GPV and strategic sellers receive the right outreach.
    
    
  
  
  • Diagnose and Act on Churn Signals
    
    
    
    • Develop dashboards and alerting systems to monitor retention performance.
    
    
    • Define seller health metrics and collaborate with Data Science to predict churn risk.
    
    
    • Lead A/B tests and reactivation experiments across channels (email, in-app, AM-led).
    
    
  
  
  • Drive Cross-Functional Execution
    
    
    
    • Collaborate across Engagement, Monetization, and Onboarding to create a cohesive retention loop.
    
    
    • Influence company-wide priorities by advocating for seller needs during churn moments.
    
    
    • Partner with GTM on incentive structures and lifecycle communication strategies.
    
    
  
  

You Have

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      • 10+ years of product management experience, with strong experience in retention, churn reduction, or customer lifecycle.
      
      
      • A track record of using data and experimentation to drive product impact.
      
      
      • Experience with save flows, subscription churn analysis, or customer winbacks is a plus.
      
      
      • Strong cross-functional execution skills, especially with Support, Sales, and Data Science.
      
      
      • A strategic mindset with attention to execution details.
      
      
    
    
  
  

Why This Role?

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        • Own a Critical Metric: Seller retention is a key driver of Square’s long-term business health.
        
        
        • Company-Wide Impact: You’ll influence product, GTM, and support strategy across the seller lifecycle.
        
        
        • Meaningful Seller Outcomes: Your work will directly help sellers stay open, grow, and succeed.
        
        
      
      
    
    
  
  

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 also consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.

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 .

Block will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.