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The Crown Is Yours

People Technology Senior Manager (L6)

The People Technology Senior Manager will lead a high-impact team responsible for the strategy, governance, configuration, optimization, and ongoing operation of Workday as an enterprise platform.

This role is ideal for a strategic, hands-on HR technology leader with broad Workday expertise, strong people leadership capabilities, and a disciplined approach to capacity planning and operational management. You will establish priorities across project, enhancement, and business-as-usual work; build visibility into platform performance and team capacity; and ensure Workday remains stable, scalable, compliant, and aligned with the evolving needs of the business.

As the owner of the Workday platform, you will provide leadership across Core HCM, Recruiting, Time Tracking, Absence, Workday Scheduler, Payroll, Advanced Compensation, Benefits, and Talent Management. While this role primarily leads and guides the team, you must have the technical depth to review solution designs, troubleshoot complex issues, guide configuration decisions, and step directly into configuration work when additional support is needed.

This individual will manage a team of three HRIS Workday Systems Specialists and play a critical role in scaling the People Technology ecosystem in partnership with People Operations, Talent Acquisition, Payroll, Total Rewards, Talent Management, Finance, Internal Audit, and IT.

Key Responsibilities

Team and People Management

• Lead, coach, and develop a team of Workday configuration and systems specialists.

• Drive performance management, technical skill development, succession planning, and career growth across the team.

• Establish clear ownership, accountability, and operating expectations for project and business-as-usual work.

• Foster a culture of transparency, continuous improvement, collaboration, and high-quality delivery.

• Ensure the team has appropriate cross-training and coverage across critical Workday functional areas.

Workday Platform Ownership

• Serve as the overall owner of Workday as an enterprise People Technology platform.

• Provide strategic and technical leadership across Core HCM, Recruiting, Time Tracking, Absence, Workday Scheduler, Payroll, Advanced Compensation, Benefits, and Talent Management.

• Establish platform standards, governance, design principles, and configuration best practices.

• Own the overall health, stability, scalability, security, and performance of the Workday platform.

• Maintain visibility into system dependencies, technical debt, recurring issues, and platform risks.

• Guide complex configuration decisions and review solution designs to ensure they are scalable, supportable, and aligned with enterprise standards.

• Step into configuration, troubleshooting, testing, or issue resolution when additional technical leadership or hands-on support is required.

• Partner with integration, security, reporting, and downstream system owners to ensure Workday operates effectively across the broader enterprise ecosystem.

Capacity Planning and Portfolio Management

• Own capacity planning across business-as-usual support, regulatory work, platform maintenance, enhancements, releases, and strategic initiatives.

• Establish a structured intake and prioritization process that balances business impact, urgency, risk, effort, and available team capacity.

• Develop forward-looking resource plans and identify capacity constraints, skill gaps, and competing priorities.

• Maintain clear visibility into team allocation, demand, backlog, delivery commitments, and upcoming work.

• Partner with People Technology and functional leaders to make informed tradeoffs and sequence work appropriately.

• Ensure critical operational work is appropriately staffed without limiting progress on strategic priorities.

Programmatic BAU and Operational Management

• Build a repeatable operating model for Workday business-as-usual support, maintenance, and continuous improvement.

• Define and monitor platform and operational metrics, including system availability, ticket volume, backlog health, defect trends, resolution times, SLA performance, configuration throughput, release quality, and recurring issue patterns.

• Build dashboards and reporting that provide visibility into Workday platform health, team performance, capacity, and demand.

• Use operational data to identify root causes, reduce recurring issues, improve service quality, and inform investment decisions.

• Own release, enhancement, incident, problem, and defect management processes using tools such as Smartsheet, ServiceNow, and internal governance platforms.

• Establish consistent processes for requirements gathering, solution design, documentation, testing, deployment, and post-production validation.

• Lead planning and delivery for Workday’s biannual releases and other required platform updates.

• Ensure production issues are assessed, escalated, communicated, and resolved with the appropriate level of urgency.

• Maintain a sustainable balance between reactive support and proactive platform optimization.

Risk, Security, and Compliance

• Ensure Workday configuration, security, and operating processes comply with SOX, internal audit, data privacy, and enterprise control requirements.

• Partner with Internal Audit, Compliance, Payroll, Finance, and Security teams to maintain appropriate controls and evidence.

• Ensure configuration changes follow established governance, testing, approval, and migration standards.

• Identify platform risks and control gaps and drive timely remediation.

• Maintain appropriate separation of duties and oversight across configuration, testing, and approvals.

Stakeholder Partnership and Solution Delivery

• Partner with People Operations, Talent Acquisition, Payroll, Total Rewards, Benefits, Talent Management, Finance, and IT to understand business needs and translate them into scalable technology solutions.

• Facilitate requirements gathering and challenge requests when a simpler, more sustainable, or more standardized solution is available.

• Set clear expectations regarding scope, sequencing, capacity, timelines, dependencies, and tradeoffs.

• Communicate platform priorities, risks, delivery progress, and operational performance to senior stakeholders.

• Ensure enhancements improve the employee, manager, and administrative experience without creating unnecessary complexity or technical debt.

Communication and Enablement

• Communicate system updates, incidents, release impacts, and project outcomes clearly to technical and non-technical audiences.

• Promote stakeholder self-sufficiency through training, job aids, office hours, and the Workday Empowerment Program.

• Ensure internal knowledge bases and system documentation remain accurate, current, and usable.

• Establish clear documentation standards for configurations, business processes, security, testing, and operational procedures.

• Translate technical topics into concise business implications, decisions, and recommended actions.

Required Skills and Qualifications

• Bachelor’s degree in Human Resources, Information Systems, Business, Technology, or a related field, or equivalent professional experience.

• At least seven years of experience supporting, configuring, or leading Workday or comparable enterprise HR technology platforms.

• At least two years of experience managing direct reports or leading a technical systems team.

• Broad Workday experience across multiple functional areas, including Core HCM, Recruiting, Time Tracking, Absence, Workday Scheduler, Payroll, Advanced Compensation, Benefits, and Talent Management.

• Strong understanding of Workday business processes, security, reporting, configuration, testing, release management, and production support.

• Demonstrated ability to serve as the owner of an enterprise platform and establish governance, standards, and operating practices.

• Strong capacity planning, portfolio management, and work prioritization skills.

• Experience managing a combination of strategic projects, enhancements, regulatory requirements, production support, and recurring operational work.

• Demonstrated experience building and using KPIs, dashboards, and system metrics to manage platform health and team effectiveness.

• Sufficient technical depth to review configurations, guide solution design, troubleshoot complex issues, and perform hands-on configuration when needed.

• Strong program and operational management skills, including intake, backlog, incident, defect, release, and risk management.

• Experience working in SOX-controlled or similarly regulated environments.

• Familiarity with ticketing, project management, and documentation tools such as ServiceNow, Smartsheet, Jira, Confluence, or comparable platforms.

• Exceptional organizational, analytical, stakeholder management, and communication skills.

• Demonstrated ability to manage competing priorities and make sound tradeoffs in a fast-paced environment.

Preferred Qualifications

• Deep expertise in one or more complex Workday functional areas, such as Payroll, Advanced Compensation, Benefits, Time Tracking, or Talent Management.

• Experience with Workday integrations, Workday Extend, APIs, and enterprise integration patterns.

• Experience managing Workday security, reporting, calculated fields, and complex business process configurations.

• Kainos Smart Test experience.

• Experience building an HR technology operating model, platform roadmap, or center of excellence.

• Experience leading a Workday implementation, major module deployment, optimization program, or enterprise transformation.

• Strong understanding of HR, payroll, compensation, benefits, talent, and workforce management processes.

• Passion for creating a frictionless employee and stakeholder experience through smart technology, strong governance, and continuous process improvement.

Join Our Team

We’re a publicly traded (NASDAQ: DKNG) technology company headquartered in Boston. As a regulated gaming company, you may be required to obtain a gaming license issued by the appropriate state agency as a condition of employment. Don’t worry, we’ll guide you through the process if this is relevant to your role.

If this job posting does not include compensation information, this is due to a technical error that our team is working to resolve! We will repost this position with compensation information as soon as it is resolved. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.