Company Overview
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.
Job Title
Director, People Operations
Remote Location
Remote - Canada (Alberta, British Columbia, Ontario, and Saskatchewan)
Role Overview
As Director, People Operations, you will lead a global team delivering scalable, high-impact services across the employee journey. Reporting to the VP, People Operations, Rewards, and Technology (PORT), you will own onboarding, contingent workforce, service delivery, global mobility and immigration, and HR compliance. As a member of the PORT Leadership Team, you will drive business outcomes through operational excellence and deliver a frictionless employee experience. This role requires a strategic, hands-on leader with strong execution and cross-functional influence.
Job Responsibilities
- People Operations Leadership: Lead and develop a high-performing global team; establish operating models, SLAs, and metrics to improve quality and efficiency
- Contingent Workforce Management: Own contingent workforce strategy and management including vendors, compliance, and cost decisions
- Global Onboarding: Oversee global onboarding operations to deliver a consistent, high-quality new hire experience
- Strategic Initiatives: Guide People Operations workstreams for company-wide initiatives including M&A
- Cross-Functional Partnership: Drive strategic priorities in partnership with Finance, Audit, Legal, Procurement, People Technology, Talent Acquisition, Workforce Planning, HR Business Partners, and HR PMO
- Global Mobility: Oversee global mobility and immigration programs; serve as escalation point for complex immigration and relocation matters
- Service Delivery & Innovation: Own service delivery strategy and continue to modernize support model; expand support through automation, self-service, and AI
- Compliance & Governance: Own global HR Compliance program including policies, controls, risk, and governance; ensure compliance reporting (EEO-1, OFCCP) and data accuracy
- Change Leadership: Lead complex change across People Operations by aligning stakeholders to strategy and ensuring sustained adoption of new priorities
Requirements
- 10+ years in People Operations or HR Operations experience
- Experience leading global teams in complex environments
- Expertise in service delivery and platforms, compliance, contingent workforce, mobility, and immigration
- Track record leading large-scale, cross-functional initiatives
- Strong stakeholder management and influencing skills with clear communication
- Data-driven with strong operational rigor
- Balances strategy and execution with strong ownership
- Experience leveraging AI and automation to improve operations
- Strong understanding of US employment law with working knowledge of international HR compliance
Preferred Qualifications
- Experience in a global technology or SaaS company
- Experience transforming People Operations at scale across company stages
- Demonstrated focus on innovation and continuous improvement
Compensation & Benefits
The range listed 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 as well as stock in the form of Restricted Stock Units (RSUs).
AI Fluency Expectations
At Dropbox, AI fluency is a core part of how we work and grow. The role requires four key behaviors:
- AI Ownership: Use AI responsibly—protecting data, applying sound judgment, and taking accountability for quality and accuracy
- AI Experimentation: Actively explore new AI capabilities to improve workflows
- AI Leverage: Use AI as a multiplier to enhance thinking and improve impact
- AI Learning: Stay current on emerging tools and trends, continuously build skills
Travel Requirements
This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter).
Equal Opportunity Employer
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.
How to Apply
Apply online through the Dropbox careers page. Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted.