Senior Manager, People Systems & Operations

About the Role

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

You'd Be a Great Fit If…

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

Compensation and Benefits:

The expected base pay range for this position is $169,000-$212,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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