Senior Manager, People Systems & Operations
Headway · United States
- Hybrid
- Full-time
- $212,000 / year
- United States
Job highlights
- Lead HR technology strategy and operations at Headway.
- Build and optimize scalable People technology ecosystem.
- Manage and develop People Systems and Operations team.
- Partner cross-functionally for system integrations and workflows.
- Implement new tools and platforms for company growth.
About the role
About Headway
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 75,000 providers across all 50 states run their practice on our software, serving over 1 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. 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 is looking for a Senior Manager, People Systems & Operations to join the People team to lead our HR technology strategy and operations. You will work closely with the Director of Total Rewards and People Operations to build and optimize a scalable People technology ecosystem that supports Headway's growth. This is a unique opportunity to lead a team in managing our systems while enhancing the daily service experience for all Headway employees.
We're looking for a people leader with deep expertise in People Systems and Operations, including technical Workday administration skills, who is proactive and able to thrive in a high-growth environment. You will be critical to ensuring our People initiatives are supported by robust, high-performing systems that leverage emerging technologies and automation.
You Will
- 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
You'd Be a Great Fit If…
- You have 10+ years of experience in People Operations and Systems with at least 5 years specifically focused on Workday administration
- You have a track record of managing and developing a team of People professionals
- You are deeply knowledgeable and adept in Workday (HCM, Advanced Compensation, Absence & Time Tracking) and other People systems (examples: Google Workspace, CultureAmp, Greenhouse, Glean)
- You are a strategic thinker who can map out a multi-year roadmap while also executing tactical configurations and integrations
- You are highly organized and have a proven track record of managing highly complex, cross-functional projects with diverse stakeholders
- You function well in a high-paced environment, having experience managing workflows for thousands of employees and handling rapid scaling
- You're skilled in technical support and enablement, capable of training staff on new platforms and building internal knowledge centers
- You collaborate and build credibility across the organization through strong communication
Compensation And Benefits
The expected base pay range for this position is $169,000-$212,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.
We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.
Benefits offered include:
- 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
Diversity & Inclusion
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.
E-Verify & Recruitment Notice
Headway participates in E-Verify. To learn more, click here.
A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.
Key skills/competency
- People Operations
- HR Technology
- Workday Administration
- Team Management
- System Integrations
- Process Improvement
- Change Management
- Project Management
- HRIS
- Automation
Skills & topics
- People Operations
- HR Technology
- Workday
- Systems Administration
- Manager
- Operations
- HRIS
- Team Leadership
- Process Improvement
- Automation
How to get hired
- Tailor your resume: Highlight your 10+ years in People Operations, with 5+ years in Workday administration, and team leadership experience.
- Showcase project management: Detail your experience managing complex, cross-functional projects and rapid scaling in high-paced environments.
- Emphasize technical skills: Clearly state your expertise in Workday modules and other HRIS systems like Google Workspace, CultureAmp, Greenhouse, or Glean.
- Prepare for behavioral questions: Be ready to discuss your strategic thinking, problem-solving approach, and collaboration style.
- Understand Headway's mission: Connect your experience to Headway's goal of fixing mental healthcare access and demonstrate your passion for their mission.
Technical preparation
Behavioral questions
Frequently asked questions
- What are the primary responsibilities of the Senior Manager, People Systems & Operations at Headway?
- The Senior Manager, People Systems & Operations at Headway will lead the HR technology strategy and operations. This includes designing and optimizing the People Systems suite (particularly Workday), improving technology for lifecycle operations, managing a team of People Systems professionals, partnering cross-functionally on integrations, and assessing/implementing new tools to support company growth.
- What specific Workday experience is required for this role at Headway?
- The role requires at least 5 years of dedicated Workday administration experience, with a deep knowledge of Workday modules such as HCM, Advanced Compensation, Absence & Time Tracking. Experience with other People systems like Google Workspace, CultureAmp, Greenhouse, or Glean is also highly valued.
- Can you explain the growth and funding status of Headway?
- Headway is a Series D company with over $325 million in funding from prominent investors like a16z, Accel, and Spark Capital. This strong financial backing supports their mission and growth initiatives, indicating a stable and expanding organization.
- What is Headway's mission and how does this role contribute to it?
- Headway's mission is to build a new mental healthcare system that is accessible and affordable for everyone, by fixing the insurance and administrative barriers. As Senior Manager, People Systems & Operations, you will ensure the People team has robust, high-performing systems that support this mission and the company's rapid growth, enabling efficient operations and employee support.
- What is the expected base pay range for the Senior Manager, People Systems & Operations at Headway?
- The expected base pay range for this position is $169,000 to $212,000 annually, with the final salary determined by factors such as qualifications, experience, and geographic location. This role may also be eligible for an equity grant.
- What kind of team will I be managing as Senior Manager, People Systems & Operations at Headway?
- You will manage and develop a team of People systems and operations professionals. The role emphasizes fostering a culture of continuous improvement and excellence within this team, ensuring they are equipped to enhance daily service experiences and support Headway's growth.
- How does Headway support diversity and inclusion in its hiring process?