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Director of People Operations

Location: Remote
Compensation: To Be Discussed
Reviewed: Fri, Oct 16, 2026
This job expires in: 30 days

Job Summary

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

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