Program Manager, Talent & AI Enablement

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

[To be included if role is bonus eligible][Other compensation includes: discretionary bonus

es 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.

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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.