Head of Sales Development – Cash App, Afterpay

This is a fully remote position, open to applicants in California.

📋 Description

• Oversee Sales Development teams in North America and the UK, both directly and through frontline managers.

• Align teams with common standards, performance metrics, and quality expectations.

• Ensure teams meet OKRs and revenue goals.

• Manage pipeline generation, including targeting strategies, channel mix, and conversion rates through accepted and closed opportunities.

• Create reporting and inspection processes to evaluate global performance.

• Design the structure for inbound and outbound Sales Development while enhancing strategies for larger markets.

• Collaborate with B2B Marketing, Sales, Risk, Compliance, Product, Sales Strategy & Operations, and Finance.

• Set standards for lead-flow, routing, qualification, and handoff processes.

• Mentor managers, coach representatives, and develop a high-performing talent pipeline.

• Leverage AI, automation, and data to enhance targeting, research, personalization, and productivity.

• Work on capacity planning, quota assignment, and territory design using performance metrics.

⛳️ Requirements

• 8+ years of experience in sales or sales development.

• Minimum of 5 years leading sales development, BDR, or SDR teams.

• Experience overseeing both individual contributors and managers.

• Ability to navigate and operate effectively within matrixed global organizations.

• Proven experience leading teams across various regions or time zones.

• Track record of establishing repeatable processes that generate pipeline converted by sales teams.

• Strong collaboration with marketing on lead flow, qualification criteria, and handoff strategies.

• Exceptional leadership and talent development abilities.

• Strong executive presence with the capability to influence senior leadership.

• Proficient with analytics and tools for measuring and managing business performance.

• Experience scaling operations into larger markets or related experience covering SMB, mid-market, or enterprise pursuits (highly preferred).

• Hands-on experience with tools, automation, and AI in prospecting (highly preferred).

• Willingness to travel and ability to work across North America, UK, and ANZ time zones (highly preferred).

• Background in payments, fintech, or a technology business with high transaction volumes (highly preferred).

🏝️ Benefits

• Remote work opportunities.

• Comprehensive medical insurance.

• Flexible time-off policies.

• Retirement savings plans.

• Modern family planning options.