Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.
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
The range listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change.
Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).
Read more about our benefits here.
Company Description
Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.
Team Description
The Dropbox People Team is designing a workplace where every Dropbox employee can thrive. We take a human-centered, HR as a Product approach—treating programs like well-designed products shaped by employee and candidate needs, informed by data, and backed by actionable insights. Our team continuously innovates to attract, develop, and retain world-class talent while building a culture of experimentation, craft, and community. From fostering connection in our Virtual First model to scaling HR systems and offering personalized learning tools and experiences, our work evolves to support the growth and needs of our people. We think big, act fast, and adapt with agility—grounded in outcomes, empathy, and clear communication.
Virtual First
Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.
This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.
AI Fluency
AI fluency is a core part of how we work and grow. It’s not about being an expert—it’s about using these tools thoughtfully and effectively to improve your work and support others.
We look for four key behaviors in candidates:
- Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.
- Experimentation: You explore new AI capabilities and apply them to improve workflows within approved tools and practices.
- Leverage: You use AI to enhance thinking, improve efficiency, and increase your impact and your team’s.
- Learning: You stay current on emerging AI tools and trends, continuously build your skills, and share what you learn with others.
Together, these behaviors help build a workforce where technology amplifies human judgment, creativity, and impact.
Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. To learn more, see our approach to AI in hiring.
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.
