Program Manager, Talent & AI Enablement

Headway

21h•$115,000 - $179,000•Remote

About The Position

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.

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
Have a 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
As comfortable in a project tracker and a stakeholder update as you are in a workshop or a pilot

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

Benefits

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