Program Manager, Talent & AI Enablement

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:

The expected base pay range for this position is $115,000- $179,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

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

Skills Required
Owned enablement or learning programs end-to-end (design, rollout, measurement, iteration)
Regular use of AI tools and ability to teach others to use them
Experience working in or closely alongside Talent Acquisition / Recruiters
Ability to design and run AI adoption programs for teams
Experience defining success metrics and building dashboards to measure program ROI
Strong, adaptable communication style tailored to different audiences
Ability to bring structure to ambiguity and operate in a high-volume, fast-paced hiring environment