Director of People Operations & Systems (AI-Driven)

Headway

New York (NY)

On-site

USD 180,000 - 230,000

Full time

3 days ago

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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