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Head of Mid-Market Sales

US - CA - San Francisco City - Remote💼 Full-time💰 $319,000–$319,000🗓 2026-08-27 → 2026-09-26

Core

Lead the North American Mid-Market Sales team to drive revenue for Cash App and Afterpay by securing deals with high-growth and established consumer brands in retail, fashion, beauty, travel, and QSR.

Role type

Senior leadership sales executive (Head of Mid-Market Sales)

Builds

Pay Now and Pay Later products for mid-market merchants

Domain

Fintech / Consumer Payments

Deliverable

production ML models | product features | dashboards & analysis | client delivery | infrastructure | physical/clinical work

Required skills

Complex commercial negotiation at scale, leading high-performing sales teams, strategic problem solving, cross-functional influence, operational and strategic mindset, executive presence, data-driven storytelling, talent development

Preferred skills

Experience in fast-moving technology or financial services, familiarity with product development in payments, comfort with analytics tools, creative storytelling

Technologies

None explicitly listed

Responsibilities

Oversee and coach the Mid-Market Account Executives team to win business at scale; Develop cross-functional partnerships with Marketing, Finance, Product, Risk, and Legal; Build team culture and develop talent; Represent the business as a thought-leader to merchant partners; Craft and pitch sales narratives to senior decision makers; Drive portfolio strategy by centralizing sales insights; Advocate for merchant feedback internally.

Seniority

Senior, hands-on IC with team leadership

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