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Director, People Operations
Headway
Remote · United States$17,667–22,083 gross/mofull-timeHeadway Careers
Headway's People function has scaled quickly, and we're now building for our next phase of growth. We're hiring a Director, People Operations to lead the programs that shape our employees' day-to-day experience — benefits strategy and administration, immigration and leave, payroll, and the Workday roadmap and automation.
Responsibilities
- Own Headway's benefits strategy end-to-end. Assess our funding model and programming, and design and implement a refreshed strategy for our next phase of growth
- Lead a proactive overhaul of employee policies and partner with the People Ops leader to streamline employee recordkeeping
- Set the strategic roadmap for People Systems (primarily Workday) and partner with Human Intelligence and People Analytics to build agentic, self-service "front door" capabilities
- Drive change adoption. Bring the People team and broader organization along through program and workflow changes; build the training, documentation, and enablement that make new tools, programs and workflows actually stick. Measure impact over time
Languages
- Work format
- Remote
- Seniority
- Head
- Posted
- 16 Oct 2026
- Last verified
- In the last 5 days
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