Senior Manager, People Systems & Operations

Headway

Senior Manager leading HR technology strategy and operations at Headway. Enhancing employee service experience and managing People Systems for efficient growth.

Posted 4/28/2026full-timeNew York City • California, New York, Washington • 🇺🇸 United StatesSenior💰 $169,000 - $212,000 per yearWebsite

About the role

Key responsibilities & impact

Design strategic People Systems suite, including Workday optimizations in partnership with our People Systems' Engineer
Improve technology to scale Headway's lifecycle operations to provide efficient support and automations for the employee lifecycle, and the internal People team
Manage and develop a team of People systems and operations professionals, fostering a culture of continuous improvement and excellence
Partner cross-functionally (IT, People Partners, etc) to visualize and plan system integrations and workflows intuitively and securely
Scope roadmaps and timelines focused on simplicity, efficiency, and the strategic adoption of AI tools
Develop and lead Change Adoption programs, including creating training resources to ensure clarity for all staff
Evaluate service delivery success, maintaining benchmarks for resolution and response times
Continuously iterate and improve People team workflows
Assess, recommend, and implement new tools and platforms as Headway grows

Requirements

What you’ll need

10+ years of experience in People Operations and Systems with at least 5 years specifically focused on Workday administration
Track record of managing and developing a team of People professionals
Deeply knowledgeable and adept in Workday (HCM, Advanced Compensation, Absence & Time Tracking) and other People systems (examples: Google Workspace, CultureAmp, Greenhouse, Glean)
Strategic thinker who can map out a multi-year roadmap while also executing tactical configurations and integrations
Highly organized with a proven track record of managing complex, cross-functional projects with diverse stakeholders
Experience managing workflows for thousands of employees and handling rapid scaling
Skilled in technical support and enablement, capable of training staff on new platforms and building internal knowledge centers
Collaborate and build credibility across the organization through strong communication

Benefits

Comp & perks

Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Workday administrationHCMAdvanced CompensationAbsence & Time TrackingPeople OperationsChange Adoptionsystem integrationsworkflow managementtechnical supporttraining resources

Soft Skills

strategic thinkingorganizational skillsproject managementcommunicationteam managementcontinuous improvementcross-functional collaborationcredibility buildingtactical executionproblem-solving