Director, GTM Planning

Block•Bay Area, CA, United States of America, CA

21h•$217,800 - $326,800•Remote

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.