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Director, People OperationsDropbox • Winnipeg, Canada
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Director, People Operations

Director, People Operations

Dropbox • Winnipeg, Canada
23 days ago
Salary
CA$204,000.00 yearly
Job type
  • Full-time
Job description
Only available to candidates in Alberta, British Columbia, Ontario, and Saskatchewan.

Director, People Operations Lead a global People Operations team delivering scalable, high‑impact services across the employee journey, including onboarding, contingent workforce, service delivery, global mobility, and HR compliance.

Responsibilities

Lead and develop a high‑performing global team

Establish operating models, SLAs, and metrics to improve quality and efficiency

Own contingent workforce strategy and management and make key decisions as it relates to the business (including vendors, compliance, cost)

Oversee global onboarding operations to deliver a consistent, high‑quality new hire experience

Guide People Operations workstreams for company‑wide initiatives (e.g., M&A)

Drive strategic priorities in partnership with Finance, Audit, Legal, Procurement, People Technology, Talent Acquisition, Workforce Planning, HR Business Partners, and HR PMO

Influence decisions and ensure execution; act as a trusted advisor on People Operations

Lead complex change across People Operations by aligning stakeholders to strategy, and ensuring sustained adoption of new priorities and ways of working

Global Mobility

Oversee global mobility and immigration programs

Serve as escalation point for complex immigration and relocation matters

Collaborate with Legal to monitor regulations and ensure compliance and program effectiveness

Service Delivery & Innovation

Own service delivery strategy and continue to modernize our support model in partnership with technology teams

Simplify and standardize employee‑facing processes and knowledge management

Expand support through automation, self‑service, and AI

Leverage data to identify friction, measure performance, and improve outcomes

Advance adoption of AI and emerging technologies to enhance the employee experience

Compliance & Governance

Own the global HR Compliance program (policies, controls, risk, governance)

Oversee HR risk initiatives (SOX, HRIS data integrity, background checks, work authorization)

Partner with Legal, Privacy, Trust & Security, and Internal Audit to strengthen controls

Ensure compliance reporting (e.g., EEO‑1, OFCCP) and data accuracy via audits

Track regulatory changes and adapt programs proactively

Requirements

10+ years in People Operations or HR Operations

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; clear communicator

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; 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 Canada Pay Range: $204,000—$276,000 CAD. The range listed above is the expected annual salary/OTE (On‑Target Earnings) for this role, subject to change.

Travel This role requires travel to offsites and various other team gatherings (approximately 5‑10% of the year or 2‑3 days per quarter).

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.

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Director, People Operations • Winnipeg, Canada

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