Director, People Operations at Headway (Remote US)

Headway helps people find therapists who take their insurance and get affordable mental health care. 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.

Key responsibilities

• Own Headway's benefits strategy end-to-end
• 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
• Rebuild contingent worker lifecycle operations on automated foundations

Requirements

• 10+ years of experience in People Operations or Total Rewards and at least 5 years managing and developing an exceptional team
• Rebuilt People workflows and support systems on automated foundations
• Fluent in modern data and automation tooling, and you understand how AI fits into the infrastructure layer of People programs — not as flashy
• Translate ambiguous business needs into a sequenced roadmap
• Communicate with clarity across audiences: crisp problem statements and solutions for leaders, specific and actionable guidance for team members
• Function well in a fast-paced environment, having experience managing workflows and data for thousands of employees and handling rapid scaling

Remote details

• Remote role in the United States

Salary and benefits

US base salary $212,000 to $265,000 a year. Headway also offers equity and benefits; the full list is on the posting.

How to apply

Apply on the company's own site.