[Hiring] Director, People Operations @Headway

Role Description

Headway's People function has scaled quickly, and we're now building for our next phase of growth. We're hiring a Director, People Operations to lead the programs that shape our employees' day-to-day experience — benefits strategy and administration, immigration and leave, payroll, and the Workday roadmap and automation. This is a high-impact role with real ownership: you'll set the direction for how these functions scale alongside the company.

You'll report to the Director of Total Rewards and Operations, lead a high-performing team, and partner closely with Finance and Legal. You'll also have a genuine seat at the table in shaping People strategy — this role is as much about influencing the function's future as it is about running it well today.

You Will...

• Own Headway's benefits strategy end-to-end. Assess our funding model and programming, and design and implement a refreshed strategy for our next phase of growth.
• Redesign employee support for leave, carrier/claims issues, general benefits questions and immigration to be both high-touch and scalable.
• Ensure accurate, timely payroll delivery that stays compliant across all states where Headway operates.
• Lead a proactive overhaul of employee policies and partner with the People Ops leader to streamline employee recordkeeping.
• Set the strategic roadmap for People Systems (primarily Workday) and partner with Human Intelligence and People Analytics to build agentic, self-service "front door" capabilities.
• Rebuild contingent worker lifecycle operations on automated foundations. Systematically replace manual, error-prone workflows with automated, AI-native ones across onboarding, offboarding, extensions, and conversions. Measure the reduction in manual effort and escalations over time.
• Drive change adoption. Bring the People team and broader organization along through program and workflow changes; build the training, documentation, and enablement that make new tools, programs and workflows actually stick. Measure impact over time.
• Coach and develop a high performing team of Managers and Associates.

Qualifications

• You have 10+ years of experience in People Operations or Total Rewards and at least 5 years managing and developing an exceptional team.
• You've rebuilt People workflows and support systems on automated foundations. You can point to workflows where you eliminated meaningful manual effort, reduced error rates, or improved SLAs through automation.
• You're fluent in modern data and automation tooling, and you understand how AI fits into the infrastructure layer of People programs — not as flashy features, but as durable, reliable process improvements.
• You translate ambiguous business needs into a sequenced 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 and solutions for leaders, specific and actionable guidance for team members.
• 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.

Company Description

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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.