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.
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 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
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.
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.
Skills Required
- 10+ years experience in People Operations and Systems
- At least 5 years of Workday administration experience
- Deep knowledge of Workday modules (HCM, Advanced Compensation, Absence & Time Tracking)
- Experience managing and developing a team of People systems or operations professionals
- Proven ability to lead complex, cross-functional system integrations and projects
- Experience with other People systems (Google Workspace, CultureAmp, Greenhouse, Glean)
- Ability to scope roadmaps, implement automations, and adopt emerging AI tools
- Strong technical support, enablement, and training experience for internal staff
- Highly organized with track record managing scaling workflows for thousands of employees
What the Team is Saying
Headway Compensation & Benefits Highlights
-
Healthcare Strength — Medical, dental, and vision plans offer multiple Cigna options with the employer covering a majority of premiums. Mental-health support includes an HRA reimbursing eligible therapy costs up to $2,100 per year and access to an EAP.
-
Parental & Family Support — Up to 16 weeks of fully paid parental leave is available to eligible full-time employees. Family-forming support is enhanced through a partnership with Carrot Fertility.
-
Leave & Time Off Breadth — Flexible/generous PTO is paired with 56 hours of paid sick time and 13 paid holidays. A company year-end holiday break (Dec 25–31) is also noted.
Headway Insights
What We Do
Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
Why Work With Us
The demand for mental health care has never been higher, underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.
Gallery
Headway Offices
Remote Workspace
Employees work remotely.
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle.
