Senior Manager, People Systems & Operations

Responsibilities

• Design strategic People Systems suite, including Workday optimizations in partnership with our People Systems' Engineer
• Improve technology in order to scale Headway's lifecycle operations to provide efficient support and automations for the employee lifecycle, as well as the internal People team
• Manage and develop a team of People systems and operations professionals, fostering a culture of continuous improvement and excellence
• Partner cross-functionally (IT, People Partners, etc) to visualize and plan system integrations and workflows intuitively and securely
• For all systems workflows and programs, whether creating new or optimizing legacy processes:
  • Scope roadmaps and timelines focused on simplicity, efficiency, and the strategic adoption of AI tools
  • Develop and lead Change Adoption programs, including the creation of training resources to ensure clarity for all staff
  • Evaluate service delivery success, maintaining benchmarks for resolution and response times
  • Continuously iterate and improve People team workflows
• Assess, recommend, and implement new tools and platforms as Headway grows

Requirements

• 10+ years of experience in People Operations and Systems with at least 5 years specifically focused on Workday administration
• Track record of managing and developing a team of People professionals
• Deeply knowledgeable and adept in Workday (HCM, Advanced Compensation, Absence & Time Tracking) and other People systems (examples: Google Workspace, CultureAmp, Greenhouse, Glean)
• Strategic thinker who can map out a multi-year roadmap while also executing tactical configurations and integrations
• Highly organized and have a proven track record of managing highly complex, cross-functional projects with diverse stakeholders
• Function well in a high-paced environment, having experience managing workflows for thousands of employees and handling rapid scaling
• Skilled in technical support and enablement, capable of training staff on new platforms and building internal knowledge centers
• Collaborate and build credibility across the organization through strong communication

Compensation and Benefits

• Expected base pay range: $169,000-$212,000, based on qualifications, experience, and location
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays + Holiday Break
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development