Head of SMB Sales

The North American SMB Sales team at Afterpay and Cash App is responsible for driving revenue to our core consumer payments businesses, giving our Merchant partners access to the largest and most engaged network of next generation consumers. We are looking for a strategic, analytical, and experienced Head of SMB Sales to build and scale a high-velocity, playbook-driven sales engine across a broad and growing base of small and medium-sized businesses, unlocking new revenue opportunities across our Buy Now Pay Later and Pay Now products. The SMB segment spans three motions: a BDR function that sources and books meetings for Account Executives, an Inbound motion serving our smaller, higher-volume businesses, and an Outbound-led motion focused on our larger, higher-growth SMB accounts. You will be responsible for orchestrating these motions into a single, cohesive system, and for the discipline, tooling, and processes that help generate pipeline and let the team convert and onboard merchants efficiently and at scale. A successful candidate exhibits a strong sense of ownership to win new business for Afterpay and Cash App, and a demonstrated ability to navigate ambiguity; think strategically and operationally about business, marketing and technical challenges; and lead cross-functional workstreams ultimately tied to pipeline creation and conversion. This role requires a strategic problem solver who is a rigorous operator and an effective influencer, comfortable balancing data-driven rigor with a strong bias for action and hands-on execution. Beyond ultimately being responsible for revenue outcomes across our SMB merchant pipeline, spanning a broad range of industries across retail, fashion, beauty, travel, home and more in North America, you'll also be building and supporting a strong culture of performance. The ideal candidate has demonstrated excellence in building and operating high-velocity sales motions at scale, leading and managing high-performing teams, and a dedication to continuous improvement. You will: • Oversee the North American SMB Sales Team: Lead a multi-motion team spanning BDR, Inbound, and Outbound Account Executives. Build and continuously refine the playbooks, processes, and tooling that let the team convert and grow merchants efficiently at high volume, moving with a bias for action and iterating quickly based on data. Craft a segment-wide strategy and hold the team accountable to delivering on OKRs and revenue targets across each motion, in concert with the broader Sales & Account Management function at Afterpay and Cash App. • Build an A-Team: You will inherit a team of strong performers with relevant experience. Further develop their skills, knowledge, efficacy, and an overall team culture focused on performance and betterment, including coaching frontline managers to drive results through their own teams. Set an energetic, accountable tone for the North America sales organization, rooted in a strong sense of ownership and led with empathy over ego. • Develop Meaningful Cross-Functional Partnerships: Work closely with cross-functional teams to better support your team in generating revenue, including Marketing, Finance, Product, Risk, Legal, Account Management and more. You can influence without authority across teams and build the internal relationships required to navigate a distributed and matrixed set of stakeholders. • Own Sales Process and Methodology: Build and refine a repeatable sales approach that covers the full deal lifecycle — from discovery and qualification through articulating value, negotiating, and closing. • Drive Forecasting Rigor and Pipeline Hygiene: Implement best practices in forecasting accuracy and pipeline health, partnering closely with Finance and Sales Ops/Strategy to keep both sharp. • Define Ideal Customer Profile and Value Proposition: Shape and sharpen our ideal customer profile, key use cases, and value proposition, and centralize and socialize the sales and growth narratives that resonate most with SMB Merchants to inform our broader B2B marketing and sales strategy. • Be the Voice of Afterpay and Cash App: Represent the business to SMB Merchants as a thought-leader in the payments and Buy Now Pay Later landscape, and demonstrate Afterpay and Cash App's value as a growth driver for small and growing businesses. • Be the Voice of the Merchant: Represent market feedback and sentiment internally, advocating for your clients while balancing against the needs and constraints of our business, by aggregating and delivering key insights across the organization in a structured, consistent, and proactive manner. You have: • An obsession with our products and a motivation fueled by feeling the impact of your work as more consumers build financial wellness with Afterpay and Cash App. • 12+ years of experience in high-growth environments leading SMB Sales, BDR, or Account Management organizations, preferably in a fast-moving technology or financial services company, with experience operating at high volume and velocity. • Excellent leadership skills with the ability to develop talent, motivate high-performing teams, and build strong cross-functional relationships, including a proven track record of coaching and managing frontline managers to results. 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. • Experience standing up or scaling sales organizations from scratch — hiring, onboarding, and developing talent across BDRs, AEs, and frontline managers. • Demonstrated ability to build, operate, and continuously improve playbooks that scale across a large and growing team. • Experience working closely with Product and Marketing to drive conversion — improving self-serve sign-up, activation, and onboarding flows to convert more prospective merchants into active partners. • Strong presence with senior internal le