Director, People Operations

Headway

8d•$212,000 - $265,000

About The Position

Headway is hiring a Director, People Operations to lead programs that shape employees’ day-to-day experience as the People function scales. The role owns benefits strategy and administration, immigration and leave, payroll, and the Workday roadmap and automation. It has strategic ownership over how these functions develop alongside the company and contributes to the future direction of the People function. The Director reports to the Director of Total Rewards and Operations, leads a team of Managers and Associates, and partners closely with Finance and Legal. The role also collaborates with Human Intelligence, People Analytics, and the People Ops leader to improve systems, records, employee support, and workflows. A key focus is replacing manual, error-prone processes with automated, AI-enabled workflows and measuring their impact, while ensuring effective change adoption through training, documentation, and enablement.

Requirements

10+ years of experience in People Operations or Total Rewards.
At least 5 years of experience managing and developing a team.
Experience rebuilding People workflows and support systems using automation, with examples of reducing manual effort or error rates, or improving service-level agreements.
Fluency with modern data and automation tools and an understanding of how AI can support reliable process improvements in People programs.
Ability to translate ambiguous business needs into a sequenced roadmap and anticipate future needs.
Clear communication with leaders and team members, including concise problem statements and actionable guidance.
Experience managing workflows and data for thousands of employees in a fast-paced, rapidly scaling environment.
Ability to collaborate and build credibility across an organization through communication, relationships, and delivery of insights.
Strong organization and a track record of managing complex cross-functional projects with diverse stakeholders.

Nice To Haves

Familiarity with HR technology platforms such as Workday and Ashby, including their integration and API capabilities.

Responsibilities

Own benefits strategy end-to-end, assess the funding model and programming, and design and implement a refreshed strategy for the company’s next phase of growth.
Redesign employee support for leave, carrier and claims issues, benefits questions, and immigration to be high-touch and scalable.
Ensure accurate and timely payroll delivery while maintaining compliance 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, replacing manual workflows across onboarding, offboarding, extensions, and conversions.
Measure reductions in manual effort and escalations resulting from workflow automation.
Drive adoption of program and workflow changes by developing training, documentation, and enablement, and measuring impact over time.
Coach and develop a high-performing team of Managers and Associates.
Partner with Finance and Legal and contribute to shaping People strategy.