Senior Product Manager, Retention

Square is a technology company that has evolved to provide integrated, omnichannel solutions for sellers. The Retention team is focused on improving seller retention and increasing the lifetime value of Square users by identifying friction points and implementing effective retention strategies.

Responsibilities:

• 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
• 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
• 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)
• 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

Requirements:

• 8+ 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
• Strong cross-functional execution skills, especially with Support, Sales, and Data Science
• A strategic mindset with attention to execution details
• Experience with save flows, subscription churn analysis, or customer winbacks is a plus