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

Job Description

The Sales Development team at Cash App is responsible for creating and qualifying the demand that drives revenue to our core consumer payments businesses, Afterpay and Cash App Pay, giving our Merchant partners access to the largest and most engaged network of next generation consumers. Sales Development is where many of our best-fit merchants first hear from us, and where we create the pipeline our sales organization converts.

We are looking for an experienced, operationally rigorous, and highly collaborative Head of Sales Development to unify and grow this program in North America & the United Kingdom. This is a newly created role, and the first time we will have led this function across markets. We have real capability in place today, with teams across the US and the UK, generating pipeline our sales organization converts, supported by playbooks and processes that work in their markets. The opportunity in front of us is to bring these teams together into a single global function and scale what is already working: shared standards where they help, one consistent view of performance, and the compounding advantage of teams learning from each other rather than solving the same problems separately. Our core motion today is SMB and there is significant opportunity to extend our more nascent upmarket motions into full-fledged parts of the program.

A successful candidate thrives in a fast-paced environment, brings a well-formed point of view on how a modern sales development function should be structured and scaled, and pairs that with the judgment to understand an existing motion deeply before evolving it. You are fluent in the measures that genuinely predict pipeline your sales teams convert rather than the activity metrics that are easiest to report, and you are comfortable building the reporting and inspection rigor that a global function requires. This role requires an effective influencer who can operate across a distributed and matrixed organization and earn the trust of leaders in other teams who do not report to you.

Beyond ultimately being responsible for top-of-funnel performance globally, you will be responsible for building and supporting a strong culture of performance and development. You excel at developing others and leading with empathy but without ego.

The ideal candidate has demonstrated excellence in building repeatable pipeline generation motions at scale, leading high performing teams across multiple markets, and a dedication to continuous improvement.

You Will

• Lead the NA & UK Sales Development Team: Lead our Sales Development teams across North America and the UK, both directly and through front-line managers. Understand what each region does well and why, then bring the function together around shared standards, a common view of performance, and a consistent bar for quality. Hold the team accountable to delivering on OKRs and contributing to revenue targets, in concert with the broader Sales & Account Management function at Cash App and Afterpay.
• Own Top-of-Funnel Performance: Carry accountability for pipeline generation across every region, including targeting strategy, channel mix, and conversion through to opportunities the sales organization accepts and closes. Build the reporting and inspection layer that makes performance legible everywhere we operate.
• Shape How the Motion Evolves: Develop and pressure-test a point of view on how Sales Development should be structured for Cash App and Afterpay as we scale, including how inbound and outbound work is organized and where the function's edges sit relative to sales and marketing. Extend the motion further upmarket, defining what needs to change in research, messaging, and coverage as merchant complexity grows.
• Develop Meaningful Cross-Functional Partnerships: Work closely with cross-functional teams to better support your team in generating pipeline, including B2B Marketing, Sales, Risk, Compliance, Product, Sales Strategy & Operations, Finance and more. Partner especially closely with B2B Marketing and regional sales leaders on lead flow, routing, qualification standards, and handoffs, bringing rigor and shared definitions to the seams between functions.
• Build a High-Performance Talent Engine: Stay close to rep development and performance while building managers who are exceptional coaches and talent developers. Set a consistent standard for coaching, accountability, and career development, creating a system that develops top performers and prepares them for quota-carrying roles.
• Define how technology enables a modern Sales Development organization: Use AI, automation, and data to improve targeting, prioritization, research, personalization, and rep productivity while reducing low-value manual work. We are an AI-forward company and we expect real leverage here.
• Bring Rigor to Planning: Partner with Sales Strategy and Finance on capacity, quota, and territory design, calibrated to the realities of each market rather than applied uniformly, and use performance data to direct capacity toward the best opportunities.

Must Have

• An obsession with our products and a motivation fueled by feeling the impact of your work as more consumers build financial wellness with Cash App & Afterpay
• 8+ years experience in sales or sales development, including 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 and where the function's boundaries sit, paired with the judgment to learn an existing motion before changing it
• 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 rather than activity
• 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. You put your people in the best position to succeed and your management style is tailored to each individual to maximize their performance and engagement at work
• Strong executive presence, with demonstrated ability to influence and earn trust with senior leaders, ask the right questions, and use sound business judgment
• Comfort working with analytics & tools that support business performance measurement & management, and the ability to build reporting rather than wait for it

Strong Plus

• 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 and specific examples of what you implemented and what it changed
• 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

Pay Transparency

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future. To find a location's zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information.

• Zone A: ($207,920 - $311,880)
• Zone B: ($193,360 - $290,040)
• Zone C: ($182,960 - $274,440)
• Zone D: ($172,560 - $258,840)