Director, People Operations

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

You'd Be a Great Fit If...

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

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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