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

The People Technology team at Dropbox is transforming how employees experience work through scalable, innovative, and human-centered technology solutions. We are seeking a Senior Workday Analyst to help modernize and optimize our People Technology ecosystem by solving complex challenges, improving workflows, and delivering impactful employee experiences across the full employee lifecycle.

This is a highly visible role that partners cross-functionally with People Operations, Compensation, Benefits, Payroll, L&OD, Talent Acquisition, IT, and business leaders to design and deliver scalable Workday solutions that improve operational efficiency, strengthen decision-making, and elevate the employee experience.

The ideal candidate brings deep Workday expertise, strong technical and analytical skills, and a product-minded approach to problem solving. They are naturally curious, challenge legacy processes, and continuously seek opportunities to simplify workflows, modernize systems, and create scalable solutions that balance business needs, compliance, and user experience.

In this role, you will help shape People Technology strategy, lead modernization initiatives, optimize Workday capabilities, and influence the long-term evolution of Dropbox’s People systems. This is an opportunity to make both immediate and lasting impact in a fast-paced environment where innovation, collaboration, and continuous improvement are highly valued.

Responsibilities

• Lead advanced configuration, optimization, testing, troubleshooting, and maintenance across Workday Core HCM and multiple functional areas including Talent & Performance, Compensation, Benefits, Reporting, Security, Learning, and Talent Optimization.
• Serve as a techno-functional SME designing scalable, compliant, and employee-centric Workday solutions that improve operational efficiency and user experience.
• Architect and maintain Workday security frameworks, governance models, and SOX-compliant controls in partnership with IT, Security, and Compliance teams.
• Design and maintain complex business processes, calculated fields, reports, dashboards, hubs, analytics solutions, matrix/composite reports, and EIBs to support data-driven decision making and operational visibility.
• Enhance talent optimization capabilities through Workday Skills Cloud, Career Hub, and Talent & Performance functionality to support internal mobility, skills visibility, and employee growth.
• Leverage emerging Workday AI and automation capabilities to improve self-service, decision support, operational efficiency, and scalable employee experiences.
• Continuously improve the Workday user experience by simplifying workflows, reducing friction, and modernizing system architecture and processes.
• Establish configuration standards, testing strategies, documentation practices, and operational best practices that improve system scalability, maintainability, and reliability.
• Evaluate and improve People processes with a focus on automation, scalability, workflow efficiency, and employee experience.
• Challenge legacy approaches and identify opportunities to simplify operations and modernize workflows.
• Apply product management and design thinking principles including roadmap planning, user journey mapping, prioritization, rapid prototyping, and iterative improvement.
• Partner cross-functionally to translate business needs into scalable technical solutions and provide consultative guidance on Workday capabilities, process design, and People Technology strategy.
• Operate as a strategic thought partner by balancing immediate business needs with long-term system health, scalability, and operational efficiency.
• Drive data-informed decision making through advanced reporting, dashboards, workforce analytics, and actionable insights.
• Stay current on evolving Workday capabilities, HR technology trends, AI-enabled workflows, and industry best practices.
• Support end-to-end project delivery including planning, testing, deployment, change management, adoption, and post-launch optimization.
• Foster collaboration, knowledge sharing, and operational excellence across the People Technology organization.

Requirements

• 5+ years of experience as a Workday techno-functional analyst or administrator with deep hands-on configuration expertise in Core HCM and at least two additional Workday functional domains. Experience supporting Workday implementations and large-scale enhancements is a plus.
• Strong experience with HCM Fundamentals, Business Process Configuration, Advanced Reporting (Advanced, Matrix, and Composite), Dashboards & Analytics, Calculated Fields, EIBs & Data Management, Workday Hubs, employee-facing experiences, and Security Administration & Governance.
• Functional expertise in Core HCM and at least two additional areas such as Talent Optimization / Skills, Talent & Performance, Reporting & Security, Compensation, Benefits, Time Tracking / Absence, or Learning.
• Familiarity with emerging Workday AI capabilities, intelligent automation, and Workday Agent features, with demonstrated experience leveraging AI tools in the flow of work to improve employee experience, workflow efficiency, self-service, operational effectiveness, and personal productivity.
• Product-driven mindset with a passion for continuous improvement, workflow optimization, and building scalable, employee-centric technology solutions that improve usability and simplify processes.
• Strong analytical, systems-thinking, communication, and problem-solving skills with the ability to challenge the status quo, balance business priorities with long-term system sustainability, build trusted cross-functional relationships, and effectively present recommendations and technical concepts to technical and non-technical audiences, including senior leadership.
• Ability to treat employee experience as a product, applying product management and design thinking to understand needs, prototype solutions, and drive execution through strong project management and data-driven iteration.
• Ability to thrive in fast-paced, evolving environments while managing competing priorities with strong attention to detail, collaboration, knowledge sharing, and operational excellence.

Preferred Qualifications

• Experience managing full Workday project lifecycles, including planning, deployment, change management, and adoption.
• Bachelor’s degree in a relevant field or equivalent practical experience preferred.
• Enthusiasm for process improvement, data integrity, and exploring evolving Workday capabilities and features.
• Demonstrated ability to conceptualize employee experience as a product, applying product management principles such as roadmap planning, user journey mapping, and feature prioritization to HR initiatives.
• Proficiency leveraging design thinking methodologies to understand employee needs, rapidly prototype solutions, and drive measurable, data-informed improvements in engagement and experience.
• Demonstrated ability to excel in fast-paced, dynamic environments while adapting to changing business needs and maintaining strong execution quality.
• Experience fostering knowledge sharing, collaboration, and best practices across Workday and People Technology teams.

Compensation

Canada Pay Range

$101,200—$136,900 CAD

Company Description

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. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

The Dropbox People Team is designing a workplace where every Dropbox employee can thrive. We take a human-centered, HR as a Product approach—treating programs like well-designed 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 and experiences, our work evolves to support the growth and needs of our people. We think big, act fast, and adapt with agility—grounded in outcomes, empathy, and clear communication.

Virtual First

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI Principles.

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.