# Senior Manager, People Systems & Operations
**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** Remote
**Salary:** $169K-$212K
**Experience:** 10+ years
**Skills:** Workday, Workday Hcm, Workday Advanced Compensation, Workday Absence & Time Tracking, Google Workspace, Cultureamp, Greenhouse, Glean, AI Tools, Hr Systems Integrations
**Posted:** 2026-04-28
> Leads HR technology strategy and operations, optimizing Workday and other people systems to support employee lifecycle and scale operations. Manages a team, drives integrations, automations, and change adoption in a high-growth environment. Requires 10+ years experience with 5+ in Workday admin.
## Job Description
## Responsibilities
- Design strategic People Systems suite, including Workday optimizations in partnership with our People Systems' Engineer
- Improve technology in order to scale Headway's lifecycle operations to provide efficient support and automations for the employee lifecycle, as well as 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
- For all systems workflows and programs, whether creating new or optimizing legacy processes:
  - Scope roadmaps and timelines focused on simplicity, efficiency, and the strategic adoption of AI tools
  - Develop and lead Change Adoption programs, including the creation of 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
- 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 and have a proven track record of managing highly complex, cross-functional projects with diverse stakeholders
- Function well in a high-paced environment, having 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

## Compensation and Benefits
- Expected base pay range: **$169,000-$212,000**, based on qualifications, experience, and location
- Equity compensation
- Medical, Dental, and Vision coverage
- HSA / FSA
- 401K
- Work-from-Home Stipend
- Therapy Reimbursement
- 16-week parental leave
- Carrot Fertility annual reimbursement and membership
- 13 paid holidays + Holiday Break
- Flexible PTO
- Employee Assistance Program (EAP)
- Training and professional development
**Apply:** https://hotfix.jobs/jobs/senior-manager-people-systems-operations-at-headway-3047d60c-52d4-4350-a19a-1651d66ece7a
**Canonical:** https://hotfix.jobs/jobs/senior-manager-people-systems-operations-at-headway-3047d60c-52d4-4350-a19a-1651d66ece7a