Senior Director, Payroll Transformation (Director of Payroll

Senior Director, Payroll Transformation

Location:

Chevy Chase, MD — Hybrid, three days per week on-site

Assignment Type:
Permanent Hire

Compensation: $170,000–$230,000 annually

Benefits:
This position is eligible for Medical, Dental, Vision, and 401(k).

We are seeking a forward-thinking Senior Director, Payroll Transformation (Director of Payroll) to lead a major payroll transformation initiative centered on process redesign, Workday Payroll optimization, automation, and AI-enabled improvements.

This is NOT a traditional payroll maintenance role. The organization needs a strategic leader who can evaluate the current environment, challenge legacy processes, lead the Workday migration, reduce manual work, and build a modern, scalable payroll operating model.

The Senior Director will oversee payroll supporting approximately 2,500 employees across 30 states while leading transformation across people, processes, systems, and co.

• Demonstrated experience redesigning or transforming a payroll function.
• Experience leading or playing a significant leadership role in a Workday Payroll migration or implementation.
• Workday Payroll expertise beyond the end-user level, including configuration, testing, integrations, workflows, reporting, or production changes.
• Experience modernizing manual or outdated payroll processes.
• Strong understanding of payroll automation, AI-enabled process improvement, and emerging payroll technology.
• Multi-state payroll leadership experience within a complex organization.
• Experience establishing payroll controls, governance, policies, and documentation.
• Proven change-management and cross-functional leadership capabilities.
• Strong executive presence with the ability to influence and communicate effectively with C-level executives and other senior leaders.
• Ability to translate complex payroll and systems issues into clear business risks and recommendations.

• Lead the redesign and transformation of the organization's payroll function.
• Direct the Workday Payroll migration, including process mapping, data validation, testing, configuration review, implementation, and stabilization.
• Evaluate the current payroll environment and develop a comprehensive transformation roadmap.
• Redesign payroll workflows to improve accuracy, efficiency, scalability, and internal controls.
• Optimize Workday Payroll functionality, configuration, reporting, workflows, and automation.
• Reduce reliance on spreadsheets, manual processes, and individual institutional knowledge.
• Identify practical opportunities to apply AI and automation within payroll operations.
• Lead organizational change management and build stakeholder support for new technology and processes.
• Establish scalable payroll policies, controls, documentation, and standard operating procedures.
• Oversee payroll operations for approximately 2,500 employees across 30 states.
• Ensure compliance with multi-state payroll, payroll tax, wage and hour, foreign-national, and visa-related requirements.
• Improve payroll reporting, analytics, and executive-level visibility.
• Partner with Finance, Human Resources, Legal, Benefits, IT, and operational leadership.
• Communicate payroll strategy, risks, project progress, and recommendations to C-level executives.
• Lead and develop the payroll team while maintaining operational accountability.
• Establish performance metrics and drive continuous improvement following the Workday implementation.

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities.

Reasonable accommodation is available for qualified individuals with disabilities, upon request.