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Head of Strategic Product Sales

Block· 20408 S&M - Sales - Square RevOps & Enablement
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Bay Area, CA$386k - $579kfull-timePosted 3mo ago

About the role

entrepreneurial sales leader to build and lead Square/Block's Strategic Product Sales organization, accelerating adoption of high-priority products across new and existing customers, and partnering cross-functionally to design scalable cross-sell motions and go-to-market strategies.

Responsibilities

  • Build, hire, and lead a high-performing team of Product Sales Managers and Specialists.
  • Partner cross-functionally to design 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.
  • 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.
  • 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.
  • Create repeatable sales plays, messaging, competitive positioning, ROI frameworks, and commercialization strategies for broader sales impact.
  • 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.
  • Help establish best practices that increase product penetration across managed and unmanaged customer segments.
  • Drive increased adoption across Square’s strategic product portfolio, improve sales productivity and customer outcomes, and influence product commercialization with customer and market feedback.

Qualifications

  • 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.

Skills

Required:Leadership in enterprise software/saaS/fintechGo-to-market strategyCross-functional influence

Benefits

  • Remote work
  • medical insurance
  • flexible time off
  • retirement savings plans
  • modern family planning
  • other benefits
Last updated Aug 26, 2026. Interested? Apply on the company site.
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About Block

Block builds technology to increase access to the global economy.

Made up of Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto, Block, Inc. builds technology to increase access to the global economy.

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