Senior Manager, HR Systems

DraftKings — Boston, MA

At DraftKings, AI is becoming an integral part of both our present and future, powering how work gets done today, guiding smarter decisions, and sparking bold ideas. It’s transforming how we enhance customer experiences, streamline operations, and unlock new possibilities. Our teams are energized by innovation and readily embrace emerging technology. We’re not waiting for the future to arrive. We’re shaping it, one bold step at a time. To those who see AI as a driver of progress, come build the future together.

The Crown Is Yours

The People Technology Senior Manager will own Workday as an enterprise platform and lead the transformation of the team responsible for its configuration, governance, optimization, and ongoing operation. This leader will move the organization beyond reactive request fulfillment toward proactive, product-minded delivery of scalable, employee-centered solutions.

Working with the Head of People Technology and the People Technology Technical Product Lead, this role will initially manage five HRIS Workday Systems Specialists and evolve the team's structure, skills, sourcing model, and ways of working. The leader must combine broad Workday expertise with hands-on technical depth, strong people leadership, and practical experience applying AI, automation, and self-service to improve platform delivery.

What You'll Do

• Own the strategy, governance, health, security, scalability, and continuous improvement of Workday across Core HCM, Recruiting, Time Tracking, Absence, Scheduler, Payroll, Advanced Compensation, Benefits, and Talent Management.
• Lead, coach, and develop a five-person Workday platform team; assess capabilities, clarify roles and decision rights, build cross-training and succession coverage, and address skill gaps through development or hiring.
• Design and implement the future-state team structure and operating model across functional configuration, integrations and automation, data and reporting, testing and releases, security and governance, production support, and continuous improvement.
• Shift the team from reactive configuration and order taking to consultative, product-minded delivery that starts with the user problem, desired experience, measurable outcome, and most scalable solution.
• Own intake, prioritization, capacity planning, sourcing, and portfolio tradeoffs across run, improve, and transform work while protecting capacity for strategic platform improvements.
• Establish operational discipline and metrics for platform health, tickets, backlog, service levels, incidents, defects, release quality, throughput, adoption, automation impact, and self-service deflection.
• Use AI, workflow automation, integrations, and knowledge capabilities to reduce manual work, prevent avoidable demand, strengthen employee and manager self-service, and improve how the team designs, tests, documents, and supports solutions.
• Partner across the People Team, Finance, Internal Audit, IT, and external providers to align priorities, manage risk, communicate tradeoffs, and deliver compliant, scalable solutions; step into complex design or configuration work when needed.

What You'll Bring

• Bachelor's degree in Human Resources, Information Systems, Business, Technology, or a related field, or equivalent professional experience; seven or more years in Workday or enterprise HR technology and at least two years leading technical teams.
• Broad Workday expertise across multiple functional areas, ideally including Core HCM, Recruiting, Time Tracking, Absence, Scheduler, Payroll, Advanced Compensation, Benefits, or Talent Management.
• Strong technical depth in Workday business processes, configuration, security, reporting, calculated fields, testing, release management, production support, and integrations, with the ability to guide complex designs and contribute hands-on when needed.
• Demonstrated ownership of an enterprise platform, including governance, standards, controls, roadmap planning, risk management, and operation within a SOX-controlled or similarly regulated environment.
• Proven experience assessing capabilities and redesigning a team's structure, roles, skills, and operating model to move from reactive request fulfillment toward consultative, product-minded delivery.
• Strong people leadership, change leadership, capacity planning, portfolio prioritization, operational management, and experience using KPIs and dashboards to improve platform and team performance.
• Practical experience with enterprise AI tools, workflow automation, APIs, integrations, self-service, and knowledge management, including the judgment to apply appropriate governance and human oversight.
• Executive presence and excellent communication, stakeholder management, and vendor leadership skills, with the ability to frame problems, challenge requests constructively, explain tradeoffs, and align senior cross-functional partners.

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.