Senior Manager, People Technology & Analytics

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's People function has scaled fast and now we're building the next layer. As we grow, we're investing in the centralized analytics capabilities, automated infrastructure, and AI-native operations that turn a high-performing People team into a genuinely predictive, self-service one.

We're hiring a Senior Manager, People Technology & Analytics to lead that transformation. The mandate: build centralized analytics capabilities the People team can trust, automate the workflows that are consuming manual effort across the employee lifecycle, and design a tech stack that scales with the company, all with AI embedded in the infrastructure, not bolted on as point-solutions.

You'll report to the Director of Total Rewards and People Operations and lead a high-performing team. You'll work closely with IT and Engineering and you'll have a genuine seat at the table on People strategy.

You Will

• Build our People analytics foundation. Design and scale a certified workforce metric ecosystem: standardized definitions, clear ownership, quality controls, and the data pipelines and semantic infrastructure that make analytics trustworthy and self-service across the People team. This includes predictive analytics capabilities such as attrition modeling, workforce planning, and other forward-looking insights that help leaders make better decisions
• Rebuild lifecycle operations on automated foundations. Systematically replace manual, error-prone workflows with automated, AI-native ones across recruiting, onboarding, comp cycles, and employee support; measure the reduction in manual effort and escalations over time
• Own the People tech stack strategy. Set the architectural direction for how Workday, Ashby, Glean, CultureAmp, Pave, Brighthire, and future tools integrate and operate together; evaluate new tools and vendors with rigor; make deliberate build/buy/integrate decisions
• Govern our AI usage and set People team standards. Establish the governance frameworks that make AI-assisted workflows reliable and intentional
• Lead and develop a high-performing team: manage and grow direct reports, set clear KPIs, and build a culture of craft and continuous improvement
• Drive change adoption. Bring the People team and broader organization along through system changes; build the training, documentation, and enablement that make new tools and workflows actually stick

You'd Be a Great Fit If…

• You have 8+ years of experience in People technology or analytics and at least 3 years managing and developing an exceptional team
• You've rebuilt People operations on automated foundations. You can point to workflows where you eliminated meaningful manual effort, reduced error rates, or improved SLAs through automation.
• You've owned a multi-system HR tech stack and made deliberate architectural decisions about how systems connect, share data, and scale; you know when to automate vs. when to keep it manual.
• You have experience building predictive analytics for People use cases: attrition, workforce planning, compensation equity, or similar.
• You're fluent in modern data and automation tooling, and you understand how AI fits into the infrastructure layer of People operations — not as flashy features, but as durable, reliable process improvements.
• You translate ambiguous business needs into a sequenced technology roadmap. You don't just react to requests, you anticipate what's coming and build for it.
• You can communicate with clarity across audiences: crisp problem statements for People leaders, specific and buildable requirements for engineers and technical partners.
• Experience taking solutions from concept through to production deployment, including navigating technical, organizational, and data infrastructure realities.
• You function well in a fast-paced environment, having experience managing workflows and data for thousands of employees and handling rapid scaling
• You collaborate and build credibility across the organization through effective communication, strong relationships and delivery of genuine insights
• You are highly organized and have a proven track record of managing highly complex, cross-functional projects with diverse stakeholders
• Familiarity with HR technology platforms (Workday, Ashby, etc.) and their integration and API capabilities is a meaningful advantage; hands-on Workday administration is not a prerequisite.

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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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.