Director, Virtual First

Role Description

Dropbox’s Virtual First model reflects our mission to design a more enlightened way of working, rooted in the same simplicity, intentionality, and human-centered design that have defined our products from day one. As an early pioneer and award-winning leader in the future of work, we pair the flexibility of remote work with intentional in-person connection to build trust, strengthen collaboration, and accelerate impact. This approach has helped cultivate a high-impact, high-growth environment where Dropboxers can do meaningful work from anywhere while continuing to innovate and thrive.

As the Director of Virtual First, you will be a strategic, highly visible leader responsible for driving the evolution and continuous improvement of our operating model. Reporting into the VP of Employee Experience, you will partner across the People organization and broader business, including the Office of the CEO, Real Estate and Workplace Services, Corporate IT, Internal & External Communications, Events, and product teams, to shape how we work, collaborate, and connect in a primarily remote environment. Your leadership will directly influence how 2,000+ Dropboxers experience work each day and ensure Dropbox remains a category leader in flexible, human-centered, high-performance work design. In this role, you will lead the core strategy and execution of Virtual First, guiding a team of program managers and specialists to design and deliver company-wide collaboration, connection, and distributed work practices at scale.

The ideal candidate is an experienced, forward-thinking operator who balances strategic vision with exceptional executional rigor. You have led complex, enterprise-wide programs that drive behavior change, improve ways of working, and shape culture, ideally in distributed or remote-first environments. You can set a bold Virtual First strategy and also roll up your sleeves to operationalize it through strong program design, cross-functional partnership, and clear communication. As an experienced people manager, you develop high-performing teams with clarity and empathy. You thrive in ambiguity, navigate organizational complexity with ease, and build alignment across diverse stakeholders. You bring deep expertise in program management, collaboration practices, and experience design, along with a bias for innovation and continuous improvement. Above all, you are energized by the opportunity to intentionally design how work happens at Dropbox.

Responsibilities

Virtual First Strategy & Vision

• Set and evolve the long-term strategy for Virtual First, translating insights, research, and business needs into the operating model

• Partner with senior leaders to align on priorities and success measures that advance our future-of-work vision

Cross-Functional Leadership & Influence

• Build strong partnerships across the Office of the CEO, Real Estate & Workplace Services, Corporate IT, Internal & External Communications, Events, and product teams to drive cohesive execution

• Influence and galvanize diverse stakeholders, regardless of reporting lines, to adopt and scale Virtual First practices

Program Design & Experience Innovation

• Design and oversee the systems, rituals, and experiences that define how we collaborate and connect in a primarily remote environment

• Leverage a product development mindset for Virtual First, ensuring that programs address employee needs and drive the right outcomes in a remote-first environment

• Innovate new approaches to distributed work, leveraging design thinking, AI, and evolving employee needs

Team Leadership

• Lead and develop a team of seven program managers and specialists responsible for delivering Virtual First programs at scale

• Set vision, priorities, and operating rhythms that enable the team to execute with clarity, creativity, and operational excellence

Operational Excellence & Planning

• Ensure all Virtual First programs, including connection rituals, in-person gatherings, and collaboration systems, are executed effectively, on time, and aligned to intended outcomes

• Establish operational rhythms, feedback loops, and continuous improvement processes to enhance quality and efficiency

• Plan and allocate team resources to deliver a large portfolio of programs on time and on budget

• Manage the team budget and quarterly budget updates with the Finance Team

Communication & Change Leadership

• Craft clear, compelling narratives that help Dropboxers understand and adopt Virtual First ways of working

• Serve as an internal thought leader and spokesperson, role-modeling Virtual First behaviors and elevating Dropbox’s position as an industry pioneer

Insights, Measurement & Continuous Improvement

• Partner with People Analytics to define metrics, assess program impact, measure ROI, and identify opportunities to evolve our model

• Benchmark industry trends and best practices to ensure Dropbox remains at the forefront of distributed work

Requirements

• 10+ years of experience leading large-scale, cross-functional programs in distributed, remote-first, or hybrid environments, with clear evidence of driving organizational change

• Demonstrated expertise in program and project management, with the ability to manage multiple complex initiatives from strategy through execution

• Proven ability to influence and partner with senior leaders and diverse stakeholder groups to drive alignment and adoption across an organization

• Experience applying design thinking, user-centered design, or experience design methodologies to create scalable, human-centered systems, programs, or processes

• Strong communication skills, including the ability to synthesize complex information and deliver clear, compelling written and verbal narratives

• Proficiency using data and insights to inform strategy, evaluate program effectiveness, and guide continuous improvement

• Bachelor’s Degree

Preferred Qualifications

• Experience partnering with product teams to share program insights, pilot results, and employee behavior data to inform product roadmaps and collaboration tooling

• Experience leveraging AI and emerging technologies to enhance collaboration, streamline program operations, or shape future-of-work practices within distributed or hybrid organizations

• Experience serving as an external thought leader (including speaking, panels, or industry forums) to elevate organizational credibility and share insights on the future of work, culture, or distributed collaboration

• Proficiency in data and analytics tools (e.g., Qualtrics, Tableau)

• Master’s Degree

Compensation

Canada Pay Range
$204,000—$276,000 CAD