Director of People Operations & Automation

Headway; United States; Remote; USD 150,000 - 190,000; Full time

Job summary

Headway is hiring a Director, People Operations to lead benefits strategy and administration, immigration and leave, payroll, and the Workday roadmap. This is a high-impact role with ownership to scale these programs as the company grows.

You will lead a high-performing team of Managers and Associates, partner with Finance and Legal, and drive automation and AI-native improvements across the People function to deliver durable process excellence.

Qualifications

• 10+ years of experience in People Operations or Total Rewards.
• 5+ years managing and developing a high-performing team.
• Experience rebuilding workflows with automation and AI-driven improvements.
• Fluent in data and automation tooling for People programs.

Responsibilities

• Own Headway's benefits strategy end-to-end, including funding model and refreshed programs.
• Redesign leave, carrier/claims issues, benefits inquiries and immigration for scalability.
• Ensure accurate payroll delivery compliant across all states Headway operates.
• Lead policy overhaul and partner with the People Ops leader on recordkeeping.
• Roadmap for People Systems (Workday) and leverage AI-native capabilities.
• Rebuild contingent worker lifecycle with automated onboarding/offboarding/extensions.
• Drive change adoption with training, docs and enablement to ensure stickiness.
• Coach and develop a high-performing team of Managers and Associates.

Skills

People Operations

Total Rewards

Team leadership

Automation tooling

Data analytics

Cross-functional collaboration

Change management

Tools

Workday

Ashby

Job description

Headway is hiring a Director, People Operations to lead benefits strategy and administration, immigration and leave, payroll, and the Workday roadmap. This is a high-impact role with ownership to scale these programs as the company grows.

You will lead a high-performing team of Managers and Associates, partner with Finance and Legal, and drive automation and AI-native improvements across the People function to deliver durable process excellence.