Director, People Operations

Headway; New York (NY); On-site; USD 180,000 - 230,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

HSA/FSA

401(k) with match

Fertility reimbursement

Parental leave

Caregiver leave

Job summary

Headway is seeking a Director, People Operations to lead benefits, immigration, payroll, and the Workday roadmap. You will drive scalable, automated processes and partner with Finance and Legal to shape People strategy while managing a high-performing team.

You'll influence the function's future and ensure compliant, data-driven operations across multiple states as the company scales rapidly.

Qualifications

• 10+ years in People Operations or Total Rewards
• 5+ years leading and developing a team
• Experience automating workflows and reducing manual effort
• Familiarity with AI in People programs
• Strong data and tooling fluency
• Ability to translate business needs into roadmaps

Responsibilities

• Own benefits strategy end-to-end and design scalable programs
• Redesign leave, immigration, and payroll processes for multi-state compliance
• Oversee Workday roadmap and automation
• Lead policies overhaul and improve employee recordkeeping
• Build front-door self-service capabilities with People Analytics
• Oversee contingent worker lifecycle automation across onboarding, offboarding, and extensions
• Drive change adoption with training and enablement
• Coach and develop a high-performing team of managers and associates

Skills

People operations leadership

Automation & AI in HR

Data-driven decisions

Change management

Cross-functional collaboration

Effective communication

Project leadership

Education

Bachelor's in HR or related field

Master's preferred

Tools

Workday

Ashby

HRIS integrations

Job description

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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

Comprehensive benefits:

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

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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