Director of People Operations

To support a growing organization, the full-time remote Director of People Operations will lead the development and execution of employee benefits strategy, payroll compliance, and automation initiatives while managing a high-performing team and collaborating closely with Finance and Legal. Key Responsibilities Own and redesign Headway's benefits strategy and employee support systems to enhance scalability and employee experience Ensure accurate and timely payroll delivery while maintaining compliance across all operational states Set the strategic roadmap for People Systems, focusing on automation and self-service capabilities Required Qualifications 10+ years of experience in People Operations or Total Rewards, with at least 5 years in a managerial role Proven experience in rebuilding People workflows on automated foundations to reduce manual effort and improve efficiency Fluency in modern data and automation tools, with a strong understanding of AI in People programs Demonstrated ability to translate business needs into actionable roadmaps and communicate effectively across various audiences Familiarity with HR technology platforms, particularly Workday, and their integration capabilities is a plus