[Hiring] Director, GTM Planning @Block

Role Description

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
• 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:

• Role mix
• Headcount requirements
• Hiring timing
• 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, including methodologies, systems, data, and processes needed to run quota, capacity, and headcount planning at scale.
• Measure whether plans are actually working and 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, defining 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.

Qualifications

• 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.

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning