People Operations Program Manager

Headway is hiring a People Operations Program Manager to serve as a strategic partner for our People team, building the systems, automations, and agentic workflows that make our teams faster and more data-informed. This role sits at the intersection of HR operations and AI-powered tooling, owning the infrastructure that enables our People team to operate at scale.

You'll own the build end-to-end, scoping problems in partnership with the HRBP team, designing the solution, launching it, and iterating based on what you learn. You'll be a builder, a systems thinker, and a trusted partner to the people doing the hard work of managing Headway's talent base.

- Own HR Business Partner (HRBP) enablement end-to-end; design, launch, and iterate on agentic tooling that make our HRBPs more effective

- Design and maintain manager operational workflows, the playbooks, tooling, and automations that help managers run their teams with less friction and more confidence

- Own the build-out and maintenance of dashboards for functional org health analytics, partnering with HR leadership to define the metrics that matter and making them visible and actionable in real time

- Lead automation of employee processes, building structured, compliant workflows that reduce manual steps and ensure consistency

- Champion responsible AI use within the HR function, partnering with Legal and IT to establish guardrails around employee data and ensure agentic HR workflows comply with employment law

- Define success metrics for everything you own; your KPIs will include automations shipped, workflow adoption, and dashboard engagement

- Own outcomes rather than outputs: gather feedback, read signals, and iterate on your programs and the workflows underneath them to ensure they deliver value

- You've owned HR operations or People programs end-to-end, designed the experience, managed the rollout, measured the impact, and iterated

- AI tools are genuinely part of how you work today; you use them, you have opinions about them, and you're already experimenting with building workflows and automations

- You can build or meaningfully contribute to agentic tools; you understand how LLMs work well enough to design prompts, evaluate outputs, and create workflows others can use

- You're comfortable getting hands-on with data and tooling to make outcomes visible; whether that's building a dashboard, wiring up an automation, or digging into an HRIS

- You've worked closely with HRBPs or in an HR generalist function and understand what slows HR teams down and how to fix it

- You have a strong yet adaptable communication style and can work effectively across HR, Legal, Engineering, and business teams

- You have managed complex, cross-functional programs with multiple stakeholders and competing timelines and have a system for keeping things on track

- You've built or maintained people analytics dashboards and know how to translate HR data into actionable insights for business leaders and managers