Head of Sales Development, North America & UK - Cash App & Afterpay

Bay Area, CA · US - CA - San Francisco City - Remote · 8+ years experience · Remote · Posted Sep 23, 2026

At a glance

Head of Sales Development, North America & UK - Cash App & Afterpay is a newly created role uniting and scaling the sales development program across North America and the United Kingdom.
The role is responsible for top-of-funnel performance globally, driving revenue to consumer payments businesses through merchant partnerships for Afterpay and Cash App Pay.

Lead the NA & UK Sales Development Team across North America and the UK directly and through front-line managers under shared standards.
Own top-of-funnel performance carrying accountability for pipeline generation, targeting strategy, channel mix, and conversion through to sales-accepted opportunities.
Shape how the motion evolves by pressure-testing structures for inbound and outbound work and extending motions upmarket.
Develop meaningful cross-functional partnerships with B2B Marketing, Sales, Risk, Compliance, Product, Sales Strategy & Operations, and Finance.
Build a high-performance talent engine, staying close to rep development while building exceptional coach managers.
Define how technology enables a modern Sales Development organization using AI, automation, and data to improve targeting and rep productivity.
Bring rigor to planning by partnering with Sales Strategy and Finance on capacity, quota, and territory design.

8+ years experience in sales or sales development
At least 5 years leading sales development, BDR, or SDR teams, with experience managing both individual contributors and managers
A well-formed point of view on how sales development should be structured and scaled, including inbound and outbound organization
Proven experience navigating and operating effectively within matrixed global organizations, and leading teams across multiple regions or time zones
A demonstrated track record of building repeatable motions that generate pipeline the sales organization converts, measured on closed-won opportunities and revenue
Strong partnership instincts with marketing, particularly on lead flow, qualification standards, and handoff design
Excellent leadership skills with the ability to develop talent, motivate high-performing teams, and build strong cross-functional relationships
Strong executive presence, with demonstrated ability to influence and earn trust with senior leaders
Comfort working with analytics and tools that support business performance measurement and management, and the ability to build reporting rather than wait for it

Experience growing a scaled motion upmarket, or credibly adjacent experience spanning both high-volume SMB coverage and more complex mid-market or enterprise pursuit
A scrappy and builder's mindset, with practical experience applying tooling, automation, and AI to prospecting
A willingness to travel, and comfort working across North America, UK, and ANZ time zones
Experience in payments, fintech, or a high-transaction-volume technology business