[Hiring] Senior Manager, People Systems & Operations @Headway

Role Description

Headway is looking for a Senior Manager, People Systems & Operations to join the People team to lead our HR technology strategy and operations. You will work closely with the Director of Total Rewards and People Operations to build and optimize a scalable People technology ecosystem that supports Headway's growth. This is a unique opportunity to lead a team in managing our systems while enhancing the daily service experience for all Headway employees.

We're looking for a people leader with deep expertise in People Systems and Operations, including technical Workday administration skills, who is proactive and able to thrive in a high-growth environment. You will be critical to ensuring our People initiatives are supported by robust, high-performing systems that leverage emerging technologies and automation.

You Will

• 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.

Qualifications

• 10+ years of experience in People Operations and Systems with at least 5 years specifically focused on Workday administration.
• A track record of managing and developing a team of People professionals.
• Deep knowledge and adeptness 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 with a proven track record of managing highly complex, cross-functional projects with diverse stakeholders.
• Experience managing workflows for thousands of employees and handling rapid scaling in a high-paced environment.
• Skilled in technical support and enablement, capable of training staff on new platforms and building internal knowledge centers.
• Strong communication skills to collaborate and build credibility across the organization.

Requirements

• Proven experience in People Operations and Systems.
• Expertise in Workday administration.
• Ability to manage and develop teams effectively.
• Experience in strategic planning and execution of technology solutions.
• Strong organizational and project management skills.
• Ability to thrive in a high-growth environment.

Benefits

• Equity compensation.
• Medical, Dental, and Vision coverage.
• HSA / FSA.
• 401K.
• Work-from-Home Stipend.
• Therapy Reimbursement.
• 16-week parental leave for eligible employees.
• Carrot Fertility annual reimbursement and membership.
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st.
• Flexible PTO.
• Employee Assistance Program (EAP).
• Training and professional development.