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Head of Mid-Market Sales

Block· 20229 S&M - Sales - Commerce Enterprise and Mid
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Bay Area, CA$319k - $478.6kfull-timePosted 3mo ago

About the role

Lead the North American Mid-Market Sales team for Cash App and Afterpay, owning revenue outcomes across a portfolio of Pay Now and Pay Later products. Responsible for complex negotiations, cross-functional collaboration, and building a scalable, performance-driven sales motion with high-growth and established mid-market brands in North America.

Responsibilities

  • Oversee the North American Mid-Market Sales Team: Lead a team of seasoned Mid-Market Account Executives. Coach the team to navigate sophisticated deal negotiations while winning business at scale. Support deal negotiations through internal and external advocacy, particularly by clearing blockers to revenue. Craft a segment-wide strategy and hold the team accountable to delivering on OKRs and executing against revenue targets, in concert with the broader Sales & Account Management function at Cash App and Afterpay.
  • Develop Meaningful Cross-Functional Partnerships: Work closely with cross-functional teams to better support your team in generating revenue, including Marketing, Finance, Product, Risk, Legal, Account Management and more. You can influence without authority across teams and build the internal relationships required to navigate a distributed and matrixed set of stakeholders.
  • Build an A-Team: You will inherit a team of strong performers with relevant experience. Further develop their skills, knowledge, efficacy and an overall team culture focused on performance and betterment.
  • Be the Voice of Cash App and Afterpay: Represent the business to leading Mid-Market Merchants as a thought-leader in the payments landscape and demonstrate Cash App and Afterpay’s value as a growth driver for our commerce partners. Develop and grow Block’s relationships with merchant partners, including their leadership teams.
  • Craft Deal Strategy: Develop and pitch powerful sales narratives that educate prospective merchants of Cash App and Afterpay’s value proposition. Effectively communicate with senior decision makers at high-growth and established brands across North America. Leverage insights, data and market intel to continuously improve our go-to-market strategy.
  • Drive Portfolio Strategy: Leverage insights across your team’s portfolio to centralize & socialize the very best sales and growth narratives that resonate with Mid-Market Merchants and inform our B2B marketing and sales strategy.
  • Be the Voice of the Merchant: Represent market feedback and sentiment internally, advocating for your clients while balancing against the needs and constraints of our business, by aggregating and delivering key insights across the organization in a structured, consistent, and proactive manner.

Qualifications

  • 12+ years experience in high-growth environments leading Mid-Market Sales, or Mid-Market Account Management organizations, preferably in a fast-moving technology or financial services company and experience working with large-scale established clients
  • Proven experience navigating and operating effectively within matrixed global organizations
  • Demonstrated track record of leading teams that consistently drive revenue growth and exceed their revenue targets
  • Excellent leadership skills with the ability to develop talent, motivate high-performing teams and build strong cross-functional relationships
  • High familiarity with product development, preferably in payments; ability to interface with stakeholders across disciplines (technical, marketing, product) and credibility with internal product and engineering teams
  • Strong executive presence with ability to influence and earn trust with senior leaders, including C-suite
  • Operational mindset with ability to implement robust processes and lead teams through complex relationships while setting a clear vision
  • Comfort working with analytics & tools that support business performance measurement & management
  • Creative storytelling abilities to build data-driven business cases for partners
  • Scrappy and humble mindset with ability to toggle between leadership and hands-on work
  • Willingness to travel

Skills

Required:Mid-Market sales leadershipCross-functional collaborationNegotiation and deal strategyExecutive stakeholder management

Benefits

  • Remote work
  • medical insurance
  • flexible time off
  • retirement savings plans
  • modern family planning
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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