Product Lead, Monetization

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 is on a mission to make commerce easy and accessible for businesses of all sizes. The Monetization team plays a critical role in this mission by increasing the adoption and utilization of Square’s paid offerings—including SaaS products (e.g., Square Loyalty, Staff Management) and banking products (e.g., Square Checking, Debit Cards).
As Product Lead, Monetization, you will be responsible for expanding seller adoption of these products, increasing processing volume, and driving incremental revenue for Square. You will build seamless product experiences that help sellers succeed while ensuring Square’s monetization strategy drives long-term value.
This is a senior leadership role that requires a deep understanding of product growth, monetization strategy, and cross-functional execution. You will work across Product, Engineering, Marketing, Sales, and Data Science to optimize adoption funnels, reduce friction, and unlock new monetization opportunities.

You Will

• Drive Adoption & Monetization
  
  • Develop and Execute Strategy: Formulate a monetization strategy aimed at increasing seller adoption of SaaS and Banking products.
  • Optimize Onboarding and Lifecycle: Enhance the onboarding and lifecycle experience to integrate these products seamlessly into seller workflows.
  • Identify Opportunities: Discover pricing, packaging, and upsell opportunities to boost retention and increase revenue per seller.
• Improve Seller Success & Processing Volume
  
  • Build Tools and Incentives: Create tools, incentives, and educational resources to help sellers boost their revenue and payment volume.
  • Collaborate with Teams: Partner with Growth, Marketing, and Sales to enable sellers to discover and adopt high-value Square products.
  • Align Strategies: Ensure monetization strategies align with seller success metrics, such as GPV growth, retention, and business expansion.
• Own Data-Driven Experimentation & Growth
  
  • Define and Track KPIs: Establish and monitor key monetization KPIs, including attach rates, conversion, churn, and LTV.
  • Conduct Experiments: Run A/B tests and growth experiments to enhance product adoption and revenue impact.
  • Leverage Data Science: Collaborate with Data Science to develop predictive models for seller monetization behaviors.
• Lead Cross-Functional Monetization Strategy
  
  • Collaborate Across Teams: Work with Product, Engineering, Marketing, and Sales to align monetization efforts with Square’s overall growth objectives.
  • Influence Go-to-Market Strategies: Shape go-to-market strategies for Square Banking, SaaS products, and new monetization initiatives.
  • Set Goals and Priorities: Collaborate with leadership to establish monetization goals, priorities, and roadmaps.

You Have

• 10+ years of product management experience, with a track record of driving monetization, SaaS growth, or fintech adoption.
• Deep understanding of pricing, packaging, and user activation strategies.
• Experience working with SaaS products, fintech, or marketplace ecosystems.
• Strong analytical and experimentation mindset—comfortable using data to drive growth decisions.
• Ability to align cross-functional teams and influence at all levels, from ICs to executives.
• Passion for helping small businesses succeed and driving real economic impact.

Why this Role?

• High Impact: You’ll drive critical revenue streams for Square and help sellers grow their businesses.
• Strategic Leadership: This role sits at the intersection of product, growth, and go-to-market.
• Massive Opportunity: Square’s SaaS & Banking products are rapidly evolving—this is a chance to shape their future.

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.