Director, People Operations

About the Role

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