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 75000 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 Senior TA Program Manager AI Enablement to build the programs and the AI-powered systems behind them that make our TA team and hiring ecosystem measurably more effective. This role sits at the intersection of two of the most important things happening at Headway: a significant tooling and process transformation in Talent and a company-wide commitment to AI adoption where every Headwegian is accountable to a measurable benchmark.

This isn't a training-room-only role. You'll lead the end-to-end implementation of AI-powered solutions across TA workflows from scoping and design through piloting launch and iteration growing your building range as you go. You'll be a program owner a coach and a change agent embedded within the Talent team helping to transform how Headway hires.

• Own hiring manager and interviewer enablement end-to-end

• Lead end-to-end implementation of AI-powered solutions and programs across TA workflows from scoping and design through piloting launch and iteration

• Own Headway’s employee referral program redesigning the program to activate our existing Headway employee network into a high-quality talent source

• Partner cross-functionally across the organization to strengthen Headway’s talent brand to help drive our candidate pipeline goals to support hiring at scale

• Design launch and scale TA enablement programs recruiter skill development tooling onboarding and documentation that scales with a high-volume fast-paced hiring environment increasingly powered by agentic workflows you create

• Define success metrics for every program you own; your KPIs will include end users enabled AI-powered solutions shipped and sustained adoption across TA and hiring teams with dashboards that make enablement ROI visible

• Pilot and scale AI-assisted approaches across recruiting tasks: job description writing candidate screening support interviewer prep and communication drafting

• Champion responsible AI use partnering with Legal Compliance and IT to establish guardrails and ensure AI-assisted hiring workflows comply with data privacy standards and employment law

• Gather feedback read the signal and iterate on your programs and the workflows underneath them

• You've owned enablement or learning programs end-to-end - 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're already experimenting with building workflows and automations (and eager to go deeper)

• You can craft effective prompts across varied workflows and understand how LLMs work well enough to teach others and quality-check their outputs

• You're comfortable getting hands-on with AI tools and real data (an ATS a tooling stack) to make outcomes visible

• You bring structure to ambiguity

• You've worked in or closely alongside Talent Acquisition and understand the Recruiter's workflow—what makes it harder or easier

• You have a strong yet adaptable communication style and can tailor it for different audiences

• You have managed complex cross-functional programs with multiple stakeholders and competing timelines and have a system for keeping things on track

• You are as comfortable in a project tracker and a stakeholder update as you are in a workshop or a pilot

Compensation and Benefits:

The expected base pay range for this position is $115000- $179000 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.

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 60000 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.

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