Head of Mid-Market Sales

Block

. Lead the North American Mid-Market Sales Team and seasoned Mid-Market Account Executives .

Posted 11/4/2026full-timeRemote • California • United StatesLead💰 $319,000 - $478,600 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in leading Mid-Market Sales teams, driving revenue growth, and developing strategic partnerships. Proven ability to influence senior leaders and navigate complex organizational structures while fostering team performance and culture.

Highest-signal resume keywords

12+ Years Experience In Mid-Market SalesRevenue Growth LeadershipCross-Functional Relationship BuildingStrategic And Operational MindsetCreative Storytelling And Data-Informed Business Cases

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Deal NegotiationRevenue Target AccountabilityMarket Intelligence UtilizationSales Narrative DevelopmentPerformance Measurement And Management

Soft Skills

Leadership And Talent DevelopmentStrong Executive PresenceInfluencing And Trust BuildingScrappy And Humble Mindset

Tools & Technologies

Analytics Tools

Industry Keywords

High-Growth EnvironmentsMid-Market Account ManagementPayments Product DevelopmentMatrixed Global OrganizationsB2B Marketing Strategy

About the role

Key responsibilities & impact

Lead the North American Mid-Market Sales Team and seasoned Mid-Market Account Executives
Coach the team through sophisticated deal negotiations and winning business at scale
Support deal negotiations by clearing internal and external blockers to revenue
Develop segment-wide strategy and hold the team accountable for OKRs and revenue targets
Partner with Marketing, Finance, Product, Risk, Legal, Account Management, and other cross-functional teams
Develop team skills, performance, and culture
Represent Cash App and Afterpay to leading Mid-Market Merchants and demonstrate their value as growth drivers
Develop and grow relationships with merchant partners and their leadership teams
Develop and pitch sales narratives and communicate with senior decision-makers
Use insights, data, and market intelligence to improve go-to-market strategy
Centralize and share effective sales and growth narratives to inform B2B marketing and sales strategy
Represent merchant feedback internally and advocate for clients
Own revenue outcomes across the North American Mid-Market merchant pipeline

Requirements

What you’ll need

12+ years experience in high-growth environments leading Mid-Market Sales or Mid-Market Account Management organizations
Preferably experience in a fast-moving technology or financial services company
Experience working with large-scale established clients
Proven experience navigating and operating effectively within matrixed global organizations
Track record of leading teams that consistently drive revenue growth and exceed revenue targets
Excellent leadership and talent-development skills
Ability to build strong cross-functional relationships
Familiarity with product development, preferably in payments
Credibility with technical, marketing, product, and engineering stakeholders
Strong executive presence and ability to influence and earn trust with senior leaders, including C-suite executives
Strategic and operational mindset
Comfort working with analytics and tools supporting business performance measurement and management
Creative storytelling abilities and ability to build data-informed business cases
Scrappy and humble mindset; willingness to work hands-on
Willingness to travel

Benefits

Comp & perks

Remote work
Medical insurance
Flexible time off
Retirement savings plans
Modern family planning
Additional benefits available through Block