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
Complete Job Description
The complete job description is available to members. Premium membership includes:
Full access to 41,175 remote jobs from human-vetted companies, updated daily
Resume Builder - AI-powered tool to craft, enhance, and tailor your resume to a specific job
Twice-monthly live group coaching and the full Remote Career Center
20% member discount on Career Services
Backed by a 30-day money-back guarantee