Program Manager Talent & AI Enablement

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 This Role

Headway is hiring a Program Manager, Talent & AI Enablement to build the programs that make our TA team and hiring ecosystem more effective. This role sits at the intersection of two of the most important things happening at Headway right now: a significant tooling and process transformation in TA, and a company-wide commitment to AI adoption where every Headwegian is accountable to a measurable benchmark.

You Will

• Design and run AI adoption programs that enable the TA team to effectively use AI in their workflows
• Build and manage TA enablement programs: Recruiter skill development, tooling onboarding, and process documentation that scales with a high-volume, fast-paced hiring environment
• Own hiring manager and interviewer enablement end-to-end
• Define success metrics for every program you own; building dashboards that make enablement ROI visible
• Partner cross-functionally to connect TA programs to the broader company strategy

You’d Be a Great Fit If

• You’ve owned enablement or learning programs end-to-end - not just created the content, but designed the experience, managed the rollout, measured the impact, and iterated
• AI tools are genuinely part of how you work today - you use them, you have opinions about them, and you can teach others to use them
• You bring structure to ambiguity
• You’ve worked in or closely alongside Talent Acquisition and understand the Recruiter’s workflow and what makes it harder or easier
• You have a strong yet adaptable communication style with the ability to tailor your communication for different audiences

Compensation and Benefits:

The expected base pay range for this position is $115,000- $179,000, 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

[To be included if role is bonus eligible][Other compensation includes: discretionary bonuses and/or commission. Commission payments are monthly.]

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.