Planning at Dropbox

Head of Workforce Strategy

Planning at Dropbox

Remote, US Canada

March 11, 2022

Dropbox is a leading global collaboration platform that’s transforming the way people work together, from the smallest business to the largest enterprise. With more than 500 million registered users across more than 180 countries, our mission is to design a more enlightened way of working. From our headquarters in San Francisco to eight dedicated Studios and a worldwide team of employees who choose where they work best, our Virtual First approach is leading the way into the future of work.

Role Description

Dropbox is looking for an experienced Head of Workforce Strategy & Planning to join the newest sub-team within Dropbox’s People organization. You will lead a small team to define and drive our workforce planning priorities by deeply understanding Dropbox’s business strategy, the internal/external landscape, and talent supply and demand. You’ll partner with the Head of Workforce Planning and Global People Services & Technology to build the long-term vision and roadmap for workforce planning and location strategy to develop new capabilities, establish new processes, and deliver projects with company-level impact. This role is ideal for someone who is “scrappy,” analytical, able to forge cross-functional partnerships, and is energized by the opportunity to build from the ground up.


  • Company Planning: Represent the Workforce Planning pillar of Dropbox’s annual company planning process in conjunction with Strategic Planning and Financial Planning. Drive the development of materials/resources and continuously optimize company planning processes. Strengthen cross-functional partnerships to ensure an integrated experience for Dropbox leaders and budget owners.

  • Workforce Strategy: Partner closely with HRBPs and Dropbox leaders to define workforce strategy and plans; establish a regular cadence and process for refreshing and refining workforce plans; roll-up and share outcomes/action plans with relevant stakeholders, including Talent Acquisition, Learning & Organization Development, and Diversity, Equity & Inclusion teams

  • Headcount Management: Be an active member of the Central Headcount Management team in partnership with Dropbox leadership, Finance, Business Operations, and Recruiting to set and manage quarterly headcount targets across the business. Support the development of workforce dashboards and reporting processes (e.g., weekly headcount tracker, location tracker, capacity planning dashboard for recruiting, etc). Facilitate change management as workforce needs or headcount targets change, partnering closely with the Recruiting team on shifting priorities for hiring.

  • Location Strategy: With support from the Location Strategy Lead, drive the evolution of Dropbox’s location strategy and roadmap for global expansion. This includes market assessment, market selection, and implementation planning/operations for market entry.

  • Workforce Planning Technology: In partnership with Finance and ITS, co-lead requirements gathering, building, testing, and implementation for WFP technology initiatives (e.g., Workday Adaptive Insights, requisition management, skills mapping).

  • Workforce Analytics: Partner with the Finance team to conduct supply and demand analysis, business scenario planning, and forecasting. Track ROI of investments and identify ways to report key metrics (e.g., cost savings, efficiencies gained). Partner with People Analytics team on workforce analytics projects, including predictive analytics, dashboards/data visualization, and identifying trends and recommendations. Conduct external benchmarking research and refresh key workforce metrics via Radford’s Global Workforce Analytics (GWA) portal to support HRBPs and business leaders with WFP discussions.

  • Strategic Workforce Planning: Define the long-term vision and three-year roadmap for Dropbox’s Workforce Planning team, including building our capability to conduct long-range talent planning, leverage talent intelligence to inform people strategy, and provide expertise in org design.


  • 8+ years experience in a global, corporate organization in a combination of Workforce Planning, Analytics, Finance, and/or Consulting roles

  • Experience partnering with Finance/FP&A on headcount management, long-range planning, and forecasting; experience with company-level planning processes required

  • Location strategy and globalization experience preferred

  • Prior people management experience required

  • Collaboration: Able to establish and maintain key cross-functional relationships across the organization (e.g., Finance, Recruiting, Chiefs of Staff); able to work effectively in a global, matrixed organization and in a virtual environment

  • Communication: Able to package and present complex analysis and recommendations; excellent verbal and written communication skills

  • Agility: Able to adapt to shifting priorities and the changing demands of business, manage ambiguity, drive results with a sense of urgency, and thrive in a fast-paced environment

  • Business Acumen: Breadth and depth of experience working with business leaders across functions; able to deeply understand the talent and financial implications of a company strategy

  • Analytics: Able to create modeling tools, dashboards, and data visualizations; ability to analyze multiple sources of information/data, identify trends, translate data into insights, and develop recommendations based on analysis

  • Technology: Foundational experience with Workday data/reporting and technology implementation required

  • Project Management: Able to lead complex cross-functional projects with multiple stakeholders or be the single driver of a project

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, Latinx, Pridebox (LGBTQ), Vets at Dropbox, Women at Dropbox, ATX Diversity (based in Austin, Texas) and the Dropbox Empowerment Network (based in Dublin, Ireland).

Benefits and Perks

  • Generous company paid individual medical, dental, & vision insurance coverage

  • 401k + company match

  • Market competitive total compensation package

  • Free Dropbox space for your friends and family

  • Wellness Reimbursement

  • Generous vacation policy

  • 11 company paid holidays

  • Volunteer time off

  • Company sponsored tech talks (technology and other relevant professional topics)