Director, Virtual First

Get AI-powered advice on this job and more exclusive features. 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. Company Description Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start‑up mindset and enterprise‑level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you’re ready to push boundaries—and yourself—Dropbox is ready for you. Team Description The Dropbox People Team is designing a workplace where every Dropboxer can thrive. We take a human‑centered, HR as a Product approach—treating programs like well‑crafted 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, we build experiences that evolve with our people. We think big, act fast, and adapt with agility—grounded in outcomes, empathy, and clear communication. Areas of work include Talent Acquisition, HR Business Partnership, Learning & Development, Total Rewards, and Employee Experience. 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. 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 $198,900—$269,100 CAD The range listed above is the expected annual salary/OTE 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). Benefits Competitive medical, dental and vision coverage* Retirement savings through a defined contribution pension or savings plan** Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more, allowing you time to unplug, unwind, and refresh Income Protection Plans: Life and disability insurance* Business Travel Protection: Travel medical and accident insurance* Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food and groceries, and much more Parental benefits including: Parental Leave, Fertility Benefits, Adoptions and Surrogacy support, and Lactation support Mental health and wellness benefits Additional Benefits Details Are Available Upon Request. Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI philosophy. 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. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox. #J-18808-Ljbffr