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

Dropbox

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