Program Manager, Talent & AI Enablement

Headway

Program Manager for Talent & AI Enablement at Headway. Designing and running AI adoption programs while collaborating cross-functionally to enhance Talent Acquisition.

Posted 5/15/2026full-timeRemote • California, New York • 🇺🇸 United StatesMid-LevelSenior💰 $115,000 - $179,000 per yearWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI adoptionprogram designsuccess metricsdashboard buildingenablement program managementprocess documentationskill development

Soft Skills

communicationadaptabilitycross-functional collaborationstructuring ambiguityexperience design