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'd Be a Great Fit If...

- 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 bring structure to ambiguity

- 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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals.

As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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