Product Lead, Engagement

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 Engagement team plays a crucial role in ensuring that sellers who start with Square stay active, use more of the product suite, and become deeply embedded in our ecosystem. As Product Lead, Engagement, you’ll be responsible for helping sellers quickly find value, take meaningful actions, and deepen their relationship with Square. You will design and scale cross-surface experiences, product nudges, and personalized recommendations that keep sellers engaged from day one. This is a senior product leadership role that requires strong systems thinking, experimentation rigor, and cross-functional leadership. You will partner closely with Product, Engineering, Design, Data Science, and Marketing to build lifecycle experiences that drive habit formation, product attachment, and long-term engagement.

You Will
Drive Engagement Across the Product Lifecycle

• Define and execute the strategy to increase daily, weekly, and monthly active seller engagement - both with business owners and with the staff running the business.
• Identify key seller moments (e.g., first invoice, second payment, first sale with hardware) and optimize for repeat usage to help sellers get maximum value from Square
• Build systems that drive cross-sell and attachment to advanced payments products, banking offerings, and SaaS tools through in-product handoffs and seller communications

Build & Scale Experimentation Systems and Execution

• Leverage ML and segmentation to target sellers with the right products and message at the right time.
• Define the metrics and health scores that best predict long-term value and retention.
• Run A/B tests across touchpoints (POS systems, backoffice dashboard, etc. and across web, app, and other channels) to increase engagement KPIs.

Collaborate Across Square

• Partner with Activation, Monetization, and Product Marketing to build an end-to-end seller journey that is delightful and useful for Square’s more than 4M sellers
• Represent the Engagement pillar in cross-functional planning and ensure seller outcomes are central to product roadmaps.
• Influence leadership on investment prioritization to scale high-performing engagement loops that turn new sellers into highly engaged and productive sellers on Square

You Have

• 10+ years of product management experience, with a track record of driving engagement in SaaS, marketplace, or fintech.
• Experience leading activation, retention, and/or overall growth teams
• Strong analytical skills and A/B testing experience.
• A systems thinker who can balance platform investments with tactical wins.
• Ability to influence cross-functional teams and senior leadership.
• A passion for helping sellers succeed and become loyal Square customers.

Why This Role?

• Critical to Square’s Growth: Increasing engagement is the foundation for product retention and monetization.
• Full Funnel Impact: You'll drive product usage across