Dropbox

Program Manager, Workforce Planning

Dropbox$128K — $173K *
US-AnywhereRemote in Canada
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in program management, business operations, or planning strategy.
  • Proven project management skills managing multiple interconnected workstreams.
  • Expertise in creating clear operational plans and timelines.
  • Strong communication skills for preparing executive-level materials.
  • Ability to identify risks and dependencies effectively.
  • Detail-oriented with excellent follow-through.
  • Experience in using data to track project delivery and adoption.

Responsibilities

  • Own and manage the Workforce Planning operating calendar.
  • Track progress across all workstreams, including milestones and risks.
  • Lead the enablement and adoption of Workforce Planning tools and policies.
  • Challenge unclear scopes and escalate risks with recommendations.
  • Package and distribute Workforce Planning insights and materials.
  • Coordinate training sessions and monitor adoption of tools and processes.
  • Prepare executive materials with input from relevant workstream owners.

Benefits

  • Opportunities for professional development and growth.
  • Access to cutting-edge tools and technology.
  • Collaborative environment with cross-functional teams.
  • Flexible working arrangements to promote work-life balance.
Full Job Description
Role Description

Reporting to the Head of Strategic Workforce Planning, this role is responsible for building and operating the systems, operating rhythms, and governance that enable the Workforce Planning team to deliver strategic work consistently and at scale.

As the owner of the Workforce Planning operating system, this person will drive the team's core planning and execution cadence, including planning cycles, governance forums, SteerCo meetings, executive reporting, quarterly organizational health reviews, and recurring team operating rhythms. They will also oversee the integrated portfolio plan across Workforce Planning workstreams, ensuring clear priorities, ownership, milestones, dependencies, and risk management to keep initiatives moving forward in a coordinated way.

In addition, this role will lead the enablement and adoption of Workforce Planning tools, outputs, and policies by managing how approved content is packaged, scheduled, distributed, and communicated to the appropriate audiences. Success requires strong program management, operational excellence, and the ability to bring structure to complex, evolving work while partnering effectively across Talent Acquisition, HR Business Partners, People Analytics, People Technology, Finance, and other cross-functional stakeholders.

This is an individual contributor role with broad responsibility for planning operations, program delivery, enablement, and cross-functional coordination, allowing Workforce Planning Business Partners to focus on strategic advisory work while ensuring the team's operating model runs effectively.
Responsibilities
  • Own the Workforce Planning operating calendar, including planning cycles, governance forums, SteerCo meetings, executive reporting, and quarterly org health reviews.
  • Support delivery across all workstreams by tracking plans, milestones, dependencies, risks, and actions.
  • Own the Enablement & Adoption operating model and its delivery infrastructure.
  • Challenge unclear scope, dates, ownership, and dependencies; escalate material risks with recommended options.
  • Package, schedule, route, and distribute approved Workforce Planning insights and materials.
  • Manage Talent Acquisition as a scaled distribution channel for Workforce Planning content.
  • Build and maintain templates, playbooks, standards, self-service resources, and enablement materials.
  • Coordinate training and education sessions and track adoption of tools, outputs, and processes.
  • Prepare recurring executive materials using content provided by the relevant workstream owners.
  • Coordinate with People Analytics and People Technology on tooling, reporting, and delivery infrastructure.
  • Maintain clear documentation of decisions, ownership, processes, and ways of working.
Requirements
  • 8 or more years of experience in program management, business operations, planning operations, or strategy and operations.
  • Strong project management skills, with the ability to manage multiple connected workstreams.
  • Ability to create clear plans, timelines, ownership, and operating rhythms.
  • Strong written and verbal communication skills, including experience preparing materials for senior leaders.
  • Ability to identify and manage risks, dependencies, and blockers.
  • Strong attention to detail and consistent follow-through.
  • Ability to work independently and effectively across teams in an evolving environment.
  • Comfort using data and feedback to track delivery and adoption.
  • Demonstrated ability to use automation and AI-enabled tools to simplify operational workflows, documentation, reporting, and knowledge management.
  • Demonstrated ability to conceptualize employee experience as a product, with proven success applying product management principles (roadmapping, user journeys, feature prioritization) to HR initiatives
  • Proficiency in leveraging design thinking methodologies to deeply understand employee needs, rapidly prototype experience solutions, and implement data-driven iteration cycles that measurably enhance engagement and retention
Preferred Qualifications
  • Exposure to workforce planning, talent planning, or finance planning.
  • Experience working with cross-functional teams such as Talent Acquisition, HR Business Partners, People Analytics, People Technology, and Finance.
  • Experience supporting planning cycles, governance forums, or the rollout of new tools and processes.
Durable Skills

AI fluency means using these tools to amplify human judgment, not replace it. We believe people with these skills will thrive as work and technology continue to evolve:
  • Awareness: Understand yourself and others.
  • Judgment: Evaluate information and make decisions in complex situations.
  • Adaptability: Learn, adjust, and stay effective through change.
  • Connection: Communicate, collaborate, and build trust.

To learn more about why these skills matter and what the data shows about thriving through change, read this blog post from our Chief People Officer, Melanie Rosenwasser.
Compensation

Canada Pay Range

$128,400-$173,700 CAD

About Dropbox

Dropbox is a publicly traded cloud storage and file sharing services company headquartered in San Francisco, California. Founded in 2007, Dropbox provides cloud storage, file synchronization, personal cloud, and client software. The company's cloud storage allows users to store and share files, photos, and videos. Dropbox has over 700 million registered users across 180 countries. The company has additional offices in New York City, Dublin, London, Paris, Sydney, and Tokyo.
Learn more about Dropbox
Size
2,667 employees
Market Cap
$8 billion
Industry
Net Income
-$256.3 million
Founded
2007
5 Year Trend
+20.6%
Revenue
$1.9 billion
NASDAQ

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