# Director, GTM Planning

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** Revenue Operations
**Salary:** $218k – $327k/yr
**Experience:** 12+ years
**Skills:** Sales Operations, Revenue Operations, Quota Planning, Capacity Planning, Headcount Planning, Salesforce, Snowflake, Pigment, Looker, Scenario Planning, Financial Modeling, Territory Design
**Posted:** 2026-08-27

> Leads quota, capacity, and headcount planning across Block’s complex commercial sales organizations, translating growth targets into hiring and productivity plans. Requires 12+ years in sales or revenue operations, GTM strategy, or strategic finance, with advanced modeling and executive influence.

## Job Description

## Responsibilities
- Build and lead quota, capacity, and headcount planning across Block’s commercial sales organizations.
- Establish the methodologies, systems, data, processes, governance, decision rights, and operating rhythms needed to run planning at scale.
- Own quota-setting for commissionable roles, incorporating market potential, pipeline, book size, productivity, ramp, attrition, role design, product mix, and route to market.
- Own commercial sales hiring models, including role mix, hiring timing, ramp assumptions, headcount requirements, and productive capacity.
- Run scenario planning covering overassignment, attainment distribution, capacity gaps, and investment tradeoffs; provide recommendations to executives.
- Advise Sales and Finance leaders on quotas, capacity, role mix, hiring, and investment decisions.
- Partner with Compensation Design to align quotas with incentive structures, seller behavior, attainment expectations, and compensation economics.
- Align Sales leadership, Finance, Strategy & Operations, and Recruiting on assumptions, decisions, and execution.
- Lead external partners through the initial planning capability build.

## 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 direct sales, channel/reseller, advertising or media sales, and account management across new business, expansion, and retention.
- Track record of building governed, scalable planning processes with clear data, decision rights, and controls.
- Advanced modeling skills and fluency with 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.
- Experience establishing a net-new planning function or capability.
- Exposure to territory design, coverage planning, or market sizing methodologies.

## Compensation and Benefits
- Annual salary range of $217,800–$326,800 USD.
- Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning.

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