Director, People Operations

• 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 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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