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 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.

You Will

• 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'd Be a Great Fit If…

• 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: