Director, People Operations

Headway

. Own Headway's benefits strategy end-to-end, including funding model assessment and refreshed strategy implementation .

Posted 10/16/2026full-timeRemote • United StatesLead💰 $212,000 - $265,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in People Operations and Total Rewards, with a strong focus on automating workflows and enhancing employee support systems. Proven ability to lead teams, manage complex projects, and implement strategic initiatives using HR technology platforms like Workday.

Highest-signal resume keywords

10+ Years Experience In People Operations5+ Years Team Management ExperienceExperience Rebuilding People WorkflowsFluency In Modern Data And Automation ToolingFamiliarity With HR Technology Platforms

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

People OperationsTotal RewardsWorkflow AutomationData ManagementProject ManagementEmployee RecordkeepingChange AdoptionAI In People ProgramsPayroll ComplianceBenefits Strategy

Soft Skills

Clear CommunicationTeam DevelopmentCoachingStakeholder ManagementChange Management

Tools & Technologies

WorkdayAshbyAutomation ToolingPeople AnalyticsSelf-Service Capabilities

Industry Keywords

Employee PoliciesContingent Worker LifecycleLeave ManagementClaims IssuesImmigration Support

About the role

Key responsibilities & impact

Own Headway's benefits strategy end-to-end, including funding model assessment and refreshed strategy implementation
Redesign employee support for leave, carrier and claims issues, benefits questions, and immigration
Ensure accurate and timely payroll delivery compliant across all states where Headway operates
Lead an overhaul of employee policies and streamline employee recordkeeping
Set the strategic roadmap for People Systems, primarily Workday
Partner with Human Intelligence and People Analytics to build agentic, self-service capabilities
Rebuild contingent worker lifecycle operations across onboarding, offboarding, extensions, and conversions using automated and AI-native workflows
Drive change adoption through training, documentation, and enablement
Measure reductions in manual effort, escalations, and workflow impact over time
Coach and develop a high-performing team of Managers and Associates
Partner closely with Finance and Legal
Report to the Director of Total Rewards and Operations

Requirements

What you’ll need

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
Experience eliminating meaningful manual effort, reducing error rates, or improving SLAs through automation
Fluency in modern data and automation tooling
Understanding of AI in the infrastructure layer of People programs
Ability to translate ambiguous business needs into a sequenced roadmap
Ability to communicate clearly across audiences
Experience managing workflows and data for thousands of employees and handling rapid scaling
Proven track record managing complex, cross-functional projects with diverse stakeholders
Familiarity with HR technology platforms such as Workday and Ashby, including integration and API capabilities is an advantage
Must be authorized to work in the United States

Benefits

Comp & perks

Equity / meaningful ownership opportunities
Robust health and wellness benefits
Retirement savings
Remote work arrangement
Reasonable accommodations for persons with disabilities