People Operations Program Manager

About the role

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 will 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 will be a builder, a systems thinker, and a trusted partner to the people doing the hard work of managing Headway's talent base. You will own HR Business Partner (HRBP) enablement end-to-end; design, launch, and iterate on agentic tooling that make our HRBPs more effective. You will design and maintain manager operational workflows, the playbooks, tooling, and automations that help managers run their teams with less friction and more confidence. You will 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. You will lead automation of employee processes, building structured, compliant workflows that reduce manual steps and ensure consistency. You will 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. You will define success metrics for everything you own; your KPIs will include automations shipped, workflow adoption, and dashboard engagement. You will own outcomes rather than outputs: gather feedback, read signals, and iterate on your programs and the workflows underneath them to ensure they deliver value.

Key facts

What you'll do

You will gather requirements from HR teams and translate them into technical specifications for automation and analytics. You will partner with Engineering to translate HR needs into product requirements and workflows. You will build and maintain integrations between HRIS, ATS, and other systems to create a seamless employee experience. You will design prompts and evaluation frameworks for AI agents that support HR workflows. You will conduct user research and interviews with HRBPs and managers to identify friction points and opportunities for improvement. You will create process documentation and training materials to support adoption of new tools and workflows. You will monitor system performance and data quality, identifying and resolving issues before they impact users. You will collaborate with People leaders to define and track people metrics tied to business outcomes. You will manage multiple workstreams simultaneously, prioritizing tasks and communicating status clearly to stakeholders. You will ensure all HR automations and data practices adhere to legal and compliance standards.

Requirements

You must have owned HR operations or People programs end-to-end, designing the experience, managing the rollout, measuring the impact, and iterating. AI tools must be genuinely part of how you work today; you use them, you have opinions about them, and you are already experimenting with building workflows and automations. You must be able to 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 must be comfortable getting hands-on with data and tooling to make outcomes visible; whether that is building a dashboard, wiring up an automation, or digging into an HRIS. You must bring structure to ambiguity and navigate open-ended problems with clarity and direction. You must have worked closely with HRBPs or in an HR generalist function and understand what slows HR teams down and how to fix it. You must have a strong yet adaptable communication style and can work effectively across HR, Legal, Engineering, and business teams. You must have managed complex, cross-functional programs with multiple stakeholders and competing timelines and have a system for keeping things on track. You must have built or maintained people analytics dashboards and know how to translate HR data into actionable insights for business leaders and managers.

Nice to have

Experience with no-code automation tools and AI agents is a plus. Background in mental health, healthcare, or mission-driven SaaS is a plus. Experience with compliance and employment law considerations in automated HR workflows is a plus.

Practical notes

This is a full-time remote role. There are no travel requirements, and no specific visa sponsorship details are provided.