Director, Quota & Capacity Planning

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

Block is looking for a Director, Quota & Capacity Planning to build and lead quota, capacity, and headcount planning across Block’s commercial sales organizations. This role turns Finance-led growth targets into actionable commercial plans: what we ask each team to deliver, the seller capacity required, and where and when we hire.

Your scope spans first-party sales (SMB through enterprise and field), third-party and channel sales (reseller and independent contractor motions), advertising and media sales, and Account Management roles with variable compensation. All of this cuts across Square and Commerce, covering new business, expansion, and retention motions.

You’ll also own the hiring model for these organizations: the role mix, headcount requirements, hiring timing, and productive capacity needed to support the plan, using planning assumptions agreed upon with cross-functional partners. Your work feeds directly into how Block invests in commercial growth. You will report to the Head of Revenue Strategy & Planning within the Revenue organization.

You Will

• Set the strategy, standards, and operating model for quota, capacity, and headcount planning across Block’s commercial sales organizations. Oversee the methodologies, models, data, tooling requirements, and processes that translate Finance-led growth targets into executable commercial plans.
• Own the quota-setting framework for all commissionable roles, translating Finance-led targets into role- and team-level quota approaches. Build differentiated methodologies that account for market potential, pipeline or run rate, book size, observed productivity, expected participation and attainment, product mix, and route to market, as relevant to each sales motion.
• Own the hiring model for the commercial sales organization. Define role mix, headcount requirements, hiring timing, and productive capacity using agreed ramp, attrition, productivity, and support-ratio assumptions. Partner with Recruiting to turn requirements into execution.
• Monitor actual productivity, participation and attainment, hiring progress, and productive capacity against plan. Identify where assumptions or outcomes are diverging and assess the implications for quota coverage, headcount, and investment.
• Lead scenario planning and executive decision-making around quota levels, overassignment, capacity gaps, role ratios, and investment tradeoffs. Shape recommendations on where Block should add, redirect, or reduce commercial investment to achieve Finance-led growth targets.
• Serve as a trusted advisor to Sales and Finance leaders, translating growth goals and performance data into clear choices about quotas, capacity, role mix, hiring, and investment.
• Partner with Compensation Design to align quota decisions with incentive structures, intended seller behavior, attainment expectations, and compensation economics.
• Lead the cross-functional operating rhythm for quota, capacity, and headcount planning, aligning Sales leadership, Finance, Strategy & Operations, Recruiting, and People partners around shared assumptions and decisions. Surface material gaps early, drive resolution, and recommend in-year changes when performance diverges from plan.

You Have

• 12+ years of experience in Sales Operations, Revenue Operations, GTM Strategy and Operations, Strategic Finance, or a related field, with significant depth in quota, capacity, and headcount planning.
• Demonstrated experience translating top-down financial targets into quota frameworks, capacity requirements, and hiring plans across a complex, multi-segment commercial organization.
• Deep knowledge of quota methodologies, productivity and capacity modeling, overassignment strategies, attainment distributions, and headcount planning.
• Experience supporting multiple go-to-market motions: direct sales, channel/reseller sales, and account management across new business, expansion, and retention.
• A track record of setting enterprise-wide standards and leading governed, scalable planning processes with clear assumptions, decision rights, controls, and executive operating rhythms.
• Strong quantitative judgment, executive presence, and cross-functional influence, with the ability to evaluate complex scenarios and translate analysis into clear investment recommendations. Fluency with systems such as Salesforce, Snowflake, Pigment, or Looker.

Bonus

• Experience in payments, fintech, or a consumption-based business model.
• You've stood up a net-new planning function or capability from scratch before.
• Exposure to territory design, coverage planning, or market sizing methodologies.

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build a workplace that is fair and square? Check out our I+D page.