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 leaders, with demonstrated ability to influence and earn trust, ask the right questions, and use sound business judgment across the organization.
• A demonstrated track record of leading teams that consistently drive revenue growth and exceed their revenue targets.
• Comfort working with analytics and tools that support business performance measurement and management, particularly around forecasting, funnel, and pipeline conversion metrics at scale.
• Creative storytelling abilities, ability to seek out relevant, meaningful data and build business cases to inform partners on Afterpay and Cash App's value proposition.
• A scrappy and humble mindset, where toggling between team lead and in-the-weeds work is business as usual. You're equally comfortable writing an annual plan as you are jumping into a pipeline review to unblock a rep. You get the job done and inspire others to do so as well.
• A willingness to travel

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.

All Zones: ($319,040 - $478,560)

Amounts listed above include target variable compensation.

Application Guidelines

Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. 

Contact us here with hiring practice or data usage questions.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

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