Director, People Operations

The role

The Director, People Operations will lead programs shaping the employee day-to-day experience including benefits, immigration, leave, payroll, and Workday roadmap. This role involves setting direction for scaling these functions and leading a high-performing team.

What you will do

• Own Headway's benefits strategy end-to-end
• Redesign employee support for leave, carrier/claims issues, general benefits questions and immigration
• Ensure accurate, timely payroll delivery across all states where Headway operates
• Lead a proactive overhaul of employee policies
• Partner with the People Ops leader to streamline employee recordkeeping
• Set the strategic roadmap for People Systems primarily Workday
• Rebuild contingent worker lifecycle operations on automated foundations
• Drive change adoption through training, documentation, and enablement
• Coach and develop a high performing team of Managers and Associates

Required qualifications

• 10+ years of experience in People Operations or Total Rewards
• At least 5 years managing and developing an exceptional team
• Experience rebuilding People workflows and support systems on automated foundations
• Fluency in modern data and automation tooling
• Understanding of how AI fits into the infrastructure layer of People programs
• Ability to translate ambiguous business needs into a sequenced roadmap
• Ability to communicate with clarity across audiences
• Experience managing workflows and data for thousands of employees and handling rapid scaling
• Ability to collaborate and build credibility across the organization
• Highly organized with a proven track record of managing complex, cross-functional projects

Nice to have

• Familiarity with HR technology platforms (Workday, Ashby, etc.) and their integration and API capabilities

Benefits

• Medical
• dental
• vision
• HSA/FSA
• 401(k) including match for 2027!
• Carrot Fertility reimbursement
• paid parental, medical and caregiver leave

Before you apply

• Headway participates in E-Verify

About the company

Headway is a Series D company building a new mental healthcare system by automating insurance, credentialing, claims, and payment reconciliation. Over 90,000 providers use their software to serve over 2.6 million patients.