People Operations Manager

Role overview

Headway is hiring a People Operations Manager to partner with the People team. You’ll build HR operations systems, automations, and agentic workflows that make HR faster and more data-informed, with a focus on infrastructure that enables the People team to operate at scale.

Responsibilities

• Own HRBP enablement end-to-end: scope needs with the HRBP team, design solutions, launch, and iterate.
• Design and launch agentic tooling to make HRBPs more effective.
• Create and maintain manager operational workflows (playbooks, tooling, automations) to reduce friction and increase confidence.
• Build and maintain dashboards for functional org health analytics; define key metrics with HR leadership and make them visible and actionable.
• Automate employee processes using structured, compliant workflows to reduce manual work and improve consistency.
• Champion responsible AI use in HR, partnering with Legal and IT to establish guardrails around employee data and ensure compliance with employment law.
• Define success metrics/KPIs for your work (e.g., automations shipped, adoption, and dashboard engagement).
• Own outcomes by gathering feedback, reading signals, and iterating based on what delivers value.

Requirements

• Experience owning HR operations / People programs end-to-end, including designing experiences, rolling out programs, measuring impact, and iterating.
• AI tools are part of your day-to-day: you actively experiment with building workflows and have informed opinions.
• Ability to build or meaningfully contribute to agentic tools; understand LLMs enough to design prompts, evaluate outputs, and create reusable workflows.
• Comfort working hands-on with data and HR tooling (e.g., building dashboards, wiring automations, analyzing HRIS/workflows).
• Ability to bring structure to ambiguity.
• Experience working with HRBPs or HR generalist functions, and understanding what slows HR teams down.
• Strong, adaptable communication across HR, Legal, Engineering, and business teams.
• Proven track record managing complex cross-functional programs with multiple stakeholders and competing timelines.