People Operations Manager

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Headway is hiring a People Operations 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. You Will 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