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

The Head of Strategic Product Sales will build and lead Block’s Product Sales organization—a specialized overlay sales team responsible for accelerating adoption of Block’s highest-priority products across both new customer acquisition and the existing customer base.

This leader will own the commercial strategy, operating model, and execution for strategic products, partnering closely with Account Executives and Account Managers to drive product adoption, expansion, and revenue growth. While AEs and AMs remain the primary relationship owners, Product Sales provides deep product expertise, engagement, and commercial leadership to maximize customer outcomes and achieve product-specific revenue goals.

What You'll Do

Build and Scale a Product Sales Organization

• Build and lead Block’s Product Sales organization, recruiting, developing, and coaching a high-performing team of leaders and product sales specialists.
• Define the organization’s operating model, territory strategy, capacity plan, and engagement model with Account Executives and Account Managers.
• Establish operating rhythms, forecasting, pipeline inspection, and performance management consistent with world-class sales organizations.
• Partner with Revenue Operations to design compensation, goals, and success metrics aligned to product revenue and customer outcomes.

Own Commercial Success for Strategic Products

• Own the commercial success of strategic products, including revenue, attach, expansion, and adoption goals.
• Develop commercialization strategies that increase adoption across both new and existing customers.
• Monitor business performance, identify growth opportunities, and lead initiatives that improve commercial outcomes.
• Partner with Sales & AM leadership to prioritize opportunities and maximize product penetration.

Partner Throughout the Sales Lifecycle

• Partner with Account Executives and Account Managers on strategic, high-value opportunities, providing product expertise, executive engagement, and deal strategy.
• Design scalable product selling motions—including webinars, masterclasses, enablement programs, and partner-led campaigns—to expand product expertise across managed and unmanaged customer segments.
• Lead executive customer conversations focused on business outcomes, solution design, competitive differentiation, and ROI.
• Help shape deal strategy and remove obstacles to winning complex opportunities.

Drive Product Commercialization

• Serve as the commercial owner for the products within your team’s portfolio.
• Develop repeatable sales plays, messaging, pricing and packaging recommendations, ROI frameworks, and competitive positioning.
• Partner with Product, Rev Ops, and Enablement to ensure successful launches and field readiness.
• Bring customer and market insights back to Product teams to influence roadmap and commercialization strategy.

Lead Cross-Functional Execution

Partner closely with Sales, Product, Marketing, Revenue Operations, Finance, Customer Success, and Enablement to:

• Launch new products successfully.
• Improve product adoption and attach rates.
• Optimize customer and seller experiences.
• Align commercial priorities across the business.

What You’ll Bring

• 10+ years of experience in enterprise software, fintech, SaaS, or payments, including significant leadership experience in sales, specialist sales, or commercial strategy.
• Experience building new organizations, operating models, or go-to-market functions in fast-growing environments.
• Proven success building and leading overlay sales or product specialist organizations.
• Track record of driving product adoption, cross-sell, and expansion revenue in complex B2B environments.
• Strong consultative selling and executive communication skills with experience engaging senior customer stakeholders.
• Experience partnering across Sales, Product, Marketing, and Operations to commercialize new products and improve go-to-market execution.
• Demonstrated ability to build scalable operating models, develop talent, and lead organizations through 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 local laws and “fair chance” ordinances. 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 takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

To find a location’s zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information. 

Zone A:

$245,000—$368,000 USD

Zone B:

$245,000—$368,000 USD

Zone C:

$245,000—$368,000 USD

Zone D:

$245,000—$368,000 USD

Amounts listed above include target variable compensation.