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 Dropbox’s Virtual First team researches, tests, and scales better ways of working for a distributed organization. We combine organizational research, experimentation, behavioral science, technology, and employee experience to continuously improve how Dropboxers work—wherever they are.

As a

Senior Program Manager

Employee Experience you will own a strategic Virtual First work stream focused on tool optimization and technology-enabled ways of working, identifying opportunities to improve employee effectiveness and translating those opportunities into research, experiments, recommendations, and scalable organizational change.

This role combines program management with research, innovation, and cross-functional stakeholder management. You will manage a portfolio of interconnected programs rather than a single project, with particular focus on knowledge management, AI enablement, and building employee confidence with tools and technology. You will establish research priorities, design and facilitate experiments, synthesize findings, and work with partners across Dropbox to turn evidence into better ways of working.

Success in this role means creating new knowledge, translating that knowledge into explicit recommendations, and driving measurable improvements in employee effectiveness, tool confidence, and adoption of AI-enabled and technology-supported ways of working.

Responsibilities

Own the strategy, roadmap, priorities, and outcomes of a Virtual First work stream focused on technology, including tools, workflows, automations,



AI enablement, and knowledge management

Design and lead organizational research, pilots, and experiments that test new ways of working

Translate qualitative and quantitative findings into actionable recommendations, behavioral frameworks, and operating models for downstream adoption

Manage a portfolio of concurrent programs and initiatives from initial scoping through research, validation, and enablement planning

Establish clear objectives, success measures, milestones, risks, and reporting across the work stream

Facilitate cross-functional Steering Committees and initiatives involving stakeholders across People, Technology, Communications, Operations, and other business functions

Partner with People Analytics and other measurement experts to establish research methodologies and evaluate outcomes

Requirements

8+ years of experience in program management, organizational effectiveness, workplace strategy, employee experience, innovation, research, or a related discipline.

Expertise in tools and technology enablement, including AI adoption, knowledge management, digital workflows, automation, and the design of technology-enabled ways of working that improve employee effectiveness.

Demonstrated experience independently leading complex, cross-functional programs from ambiguity through measurable outcomes.





Experience designing and managing research, pilots, experiments, or other evidence-based innovation programs.

Strong understanding of Virtual First, distributed, hybrid, or modern ways of working.

Excellent written, verbal, facilitation, and executive communication skills.

Comfort working in ambiguity and proactively identifying opportunities rather than waiting for assignments.

Preferred Qualifications

Experience working in a distributed or Virtual First organization.

Experience with organizational behavior, change management, behavioral science, workplace research, or human-centered design.

Demonstrated curiosity about the future of work and emerging technologies.

Durable Skills

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 incent

📌 Senior Program Manager, Employee Experience (Regina)
🏢 Dropbox
📍 Regina