Headway
Director, People Operations
$212K–$265K
Remote +3 · Remote · Director · Full-time · Posted Oct 16, 2026
- Location
- Remote
San Francisco, CA
Seattle, WA
New York City - Experience
- 10+ years in People Operations or Total Rewards; at least 5 years managing and developing a team.
- Visa sponsorship
- Participates in E-Verify.
About the job
Leads People Operations programs and strategy, including benefits, payroll, immigration and leave, People systems, automation, and employee support.
What you'll do
- Own and redesign benefits strategy and employee support for benefits, leave, immigration, and payroll.
- Set the People Systems roadmap, automate workflows including contingent worker lifecycle operations, and drive change adoption.
- Lead and develop the People Operations team and partner with Finance, Legal, and other People functions.
What they ask for
- 10+ years of experience in People Operations or Total Rewards.
- At least 5 years managing and developing a team.
- Experience rebuilding People workflows and support systems through automation, with measurable improvements.
- Experience managing workflows and data for thousands of employees and handling rapid scaling.
Nice to have
- Familiarity with HR technology platforms such as Workday and Ashby, including integrations and APIs.
Pay
$212K – $265K USD base salary
Tools
Workday, Ashby
AI focus
Build agentic, self-service People capabilities and automate contingent worker workflows with AI-native processes.
Model-written summary · the original posting is authoritative