Director, GTM 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, GTM Planning to build and lead quota and capacity planning across Block's commercial sales organizations. This is the function that turns growth targets into actionable plans: how many sellers we need, what we ask them to deliver, 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. 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

• Build and own the planning capability end to end. That means the methodologies, systems, data, and processes needed to run quota, capacity, and headcount planning at scale. Measure whether plans are actually working. Lead external partners through the initial build.
• Own the quota-setting framework for all commissionable roles, from initial target-setting through ongoing assessment. Build differentiated approaches that account for market potential, pipeline, book size, productivity, ramp, attrition, role design, product mix, and route to market.
• Own the hiring model for the commercial sales organization. Define role mix, hiring timing, ramp assumptions, and productive capacity. Partner with Recruiting to turn requirements into execution.
• Run scenario planning to evaluate overassignment, attainment distribution, capacity gaps, and investment tradeoffs. Bring clear recommendations to executive decision-makers.
• Serve as a trusted advisor to Sales and Finance leaders, translating growth goals 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.
• Align Sales leadership, Finance, Strategy & Operations, and Recruiting around shared assumptions, decisions, and execution. Flag early when plans don't tie, and propose how to close the gaps.
• Establish governance, decision rights, standards, and executive operating rhythms for planning approvals, in-year changes, and performance reviews.

You Have

• 12+ years of experience in Sales Operations, Revenue Operations, GTM Strategy and Operations, Strategic Finance, or a related field.
• Experience leading quota, capacity, and headcount planning across a complex, multi-segment sales organization.
• Deep knowledge of quota methodologies, productivity and capacity modeling, ramp and attrition assumptions, overassignment strategies, and headcount planning.
• Experience supporting multiple go-to-market motions: direct sales, channel/reseller, advertising or media sales, and account management across new business, expansion, and retention.
• A track record of building governed, scalable planning processes with clear data, decision rights, and controls.
• Advanced modeling skills and fluency with systems like Salesforce, Snowflake, Pigment, or Looker.
• Strong executive communication and cross-functional influence.

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.