Program Manager, Talent & AI Enablement

Responsibilities

• 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.

Requirements

• 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).
• Can craft effective prompts across varied workflows and understand how LLMs work well enough to teach others and quality-check their outputs.
• Comfortable getting hands-on with AI tools and real data (an ATS, a tooling stack) to make outcomes visible.
• Bring structure to ambiguity.
• Worked in or closely alongside Talent Acquisition and understand the Recruiter's workflow—what makes it harder or easier.
• Strong yet adaptable communication style and can tailor it for different audiences.
• Managed complex, cross-functional programs with multiple stakeholders and competing timelines and have a system for keeping things on track.
• Comfortable in a project tracker and a stakeholder update as you are in a workshop or a pilot.

Nice-to-Haves

• Experience building AI-powered systems or agentic workflows.
• Familiarity with ATS and recruiting tooling stacks.

Compensation and Benefits

• Expected base pay range: $115,000 - $179,000.
• Eligible for equity grant.
• Comprehensive benefits: Medical, Dental, Vision, HSA/FSA, 401K, Work-from-Home Stipend, Therapy Reimbursement, 16-week parental leave, Carrot Fertility, 13 paid holidays + Holiday Break, Flexible PTO, EAP, training and professional development.