People Operations Program Manager, AI & Automation

Headway; United States; Remote; USD 140,000 - 190,000; Full time

Job summary

Headway is seeking a People Operations Program Manager to lead the systems, automations, and agentic workflows that empower our HR teams to operate at scale. You will own the end-to-end build, scoping with HRBP, designing solutions, launching, and iterating based on outcomes.

The role sits at the intersection of HR operations and AI-powered tooling, requiring a builder mindset, systems thinking, and collaboration withLegal and IT to ensure compliant, data-informed HR workflows.

Qualifications

• Experience owning HR operations or People programs end-to-end.
• Familiar with AI tools and building agentic workflows.
• Ability to design prompts, evaluate outputs, and create reusable workflows.

Responsibilities

• Design, build, and iterate HR tooling and automations.
• Create dashboards and metrics for org health.
• Define success metrics and drive adoption across teams.
• Partner with Legal, IT, and HRBP teams to ensure compliance.

Skills

HR operations

People programs

Data analysis

Dashboarding

AI tooling

Tools

HRIS

Automation tools

LLM prompts

Data dashboards

Job description

Headway is seeking a People Operations Program Manager to lead the systems, automations, and agentic workflows that empower our HR teams to operate at scale. You will own the end-to-end build, scoping with HRBP, designing solutions, launching, and iterating based on outcomes.

The role sits at the intersection of HR operations and AI-powered tooling, requiring a builder mindset, systems thinking, and collaboration withLegal and IT to ensure compliant, data-informed HR workflows.