Head of Strategic Product Sales

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 Block is looking for an entrepreneurial sales leader to build and lead our Strategic Product Sales organization—a specialized team responsible for accelerating adoption of our highest-priority products across new and existing customers. This is a builder role. You'll partner cross-functionally to identify where we're underpenetrated, develop the commercial strategy to unlock growth, and create scalable cross-sell motions that drive product adoption at scale. You'll lead a team of product sales specialists while partnering closely with Account Executives, Account Managers, Product, Marketing, Revenue Operations, and Enablement to improve how strategic products are sold across the business. Success in this role requires equal parts commercial strategy, sales leadership, and cross-functional influence. What You'll Do Build and Scale a Product Sales Organization • Build, hire, and lead a high-performing team of Product Sales Managers and Specialists. • Partner cross-functionally to design the operating model, engagement strategy, territory approach, and capacity plan for the organization. • Establish forecasting, pipeline management, inspection rhythms, and performance metrics. • Partner with Revenue Operations to define goals, compensation, and success measures aligned to commercial outcomes. Build New Commercial Motions • Deploy targeted strategies towards underpenetrated strategic products and design scalable sales motions to accelerate adoption. • Develop commercialization strategies that increase attach rates, cross-sell, and expansion revenue. • Determine which customers to prioritize, how to engage them, and which sales resources should be deployed. • Continuously evaluate performance and refine go-to-market strategies based on customer and market insights. Lead Strategic Selling • Partner with Account Executives and Account Managers on high-value customer opportunities requiring specialized product expertise. • Lead complex commercial conversations with executive stakeholders, helping shape account strategy and maximize customer value. • Deploy your team of specialists to accelerate strategic opportunities while enabling relationship owners to remain at the center of the customer experience. • Remove barriers to winning complex, multi-product deals. Enable the Broader Sales Organization • Create repeatable sales plays, messaging, competitive positioning, ROI frameworks, and commercialization strategies that help the broader sales organization sell more effectively. • Partner with Enablement to build scalable programs including playbooks, webinars, workshops, and sales training. • Improve product expertise across Account Executives, Account Managers, and other first-party sales teams - and drive improved success metrics. • Help establish best practices that increase product penetration across managed and unmanaged customer segments. Drive Cross-Functional Execution Partner closely with Product, Marketing, Revenue Operations, Finance, Customer Success, and Sales Leadership to: • Successfully drive increased adoption across Square’s strategic product portfolio. • Increase product adoption and attach rates. • Improve sales productivity and customer outcomes. • Influence product commercialization through customer and market feedback. What You’ll Bring • 10+ years of leadership experience in enterprise software, fintech, SaaS, payments, or another complex B2B environment. • Experience building new sales organizations, commercialization functions, or strategic go-to-market motions from the ground up. • Proven success leading specialist sales, overlay sales, solution sales, or product-focused commercial organizations. • Demonstrated ability to drive cross-sell, product adoption, attach, and expansion revenue. • Strong commercial instincts with the ability to identify growth opportunities and translate them into scalable sales strategies. • Experience leading through influence and partnering across Sales, Product, Marketing, Revenue Operations, and Enablement. • Executive presence with strong consultative selling and customer engagement skills. • Track record of building high-performing teams, coaching leaders, and scaling organizations through growth and change. 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 loca