Program Manager, Talent & AI Enablement

About the 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. You will own the end-to-end implementation of AI-powered solutions across TA workflows, acting as a program owner, a coach, and a change agent embedded within the Talent team to help transform how Headway hires. This is not a training-room-only role; you will lead from scoping and design through piloting, launch, and iteration, expanding your scope and impact as you prove value and build out your program portfolio.

You will own hiring manager and interviewer enablement end-to-end, ensuring they have the tools, knowledge, and confidence to leverage new technologies effectively. You will partner cross-functionally across the organization to strengthen Headway's talent brand and drive candidate pipeline goals to support hiring at scale. You will 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, you will power these efforts with agentic workflows you create to automate and enhance recurring enablement tasks. You will define success metrics for every program you own, with KPIs that include end users enabled, AI-powered solutions shipped, and sustained adoption across TA and hiring teams. You will build dashboards that make enablement ROI visible and provide clear evidence of value to stakeholders. You will pilot and scale AI-assisted approaches across recruiting tasks such as job description writing, candidate screening support, interviewer prep, and communication drafting. You will 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. Finally, you will gather feedback, read the signal, and iterate on your programs and the workflows underneath them to drive continuous improvement.

Key facts

What you'll do

• Own hiring manager and interviewer enablement end-to-end, from needs assessment and solution design to rollout, training delivery, and continuous optimization.
• 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 and 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.
• 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.
• Pilot and scale AI-assisted approaches across recruiting tasks, including 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 to drive continuous improvement.
• Leverage data and qualitative insights to refine program content, user experience, and adoption strategies for maximum impact.
• Collaborate closely with the TA Ops and Platform teams to ensure enablement programs integrate seamlessly with core tools and processes.
• Create and maintain scalable training materials, playbooks, and job aids that support both human and AI-assisted workflows.
• Act as a subject matter expert on AI tools and their application in recruiting, translating technical capabilities into practical guidance for hiring teams.
• Run controlled experiments to test the effectiveness of new enablement initiatives and AI tools, analyzing results to inform rollout decisions.
• Communicate program status, outcomes, and learnings to senior Talent and People leaders on a regular and recurring basis.
• Identify and mitigate risks early, ensuring all enablement activities align with company policies, compliance requirements, and ethical standards.
• Develop and manage relationships with key stakeholders, building trust and influence across cross-functional teams.
• Maintain a high standard of quality and accuracy in all program deliverables, documentation, and communications.
• Support the broader Talent team in special projects related to hiring strategy, tooling adoption, and process optimization.
• Contribute to a culture of learning and experimentation, encouraging the TA team to explore new ways of working with AI.

Requirements

• You have owned enablement or learning programs end-to-end in a previous role, designing the experience, managing the rollout, measuring the impact, and iterating based on results.
• AI tools are genuinely part of how you work today; you use them, you have opinions about them, and you are already experimenting with building workflows and automations (and you are 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 are comfortable getting hands-on with AI tools and real data, including an ATS and a tooling stack, to make outcomes visible and drive decisions.
• You bring structure to ambiguity, thriving in environments where priorities shift and problems are not clearly defined.
• You have worked in or closely alongside Talent Acquisition and understand the Recruiter's workflow, including what makes it harder or easier in practice.
• You have a strong yet adaptable communication style and can tailor it for different audiences, from individual contributors to executive leadership.
• You have managed complex, cross-functional programs with multiple stakeholders and competing timelines, and you have a system for keeping things on track and ensuring accountability.
• You are as comfortable in a project tracker and a stakeholder update as you are in a workshop or a pilot session.
• You are passionate about using technology to improve how people work and are committed to ethical, responsible AI use.
• You are highly organized and meticulous, with a demonstrated ability to manage details in a fast-paced, high-volume environment.
• You are a collaborative problem-solver who seeks input from others and builds alignment before making decisions.
• You have a bias for action, balancing speed with thoughtful execution and learning.
• You are comfortable working remotely and managing your time effectively with minimal direct supervision.
• You have experience reading and interpreting data to inform decisions and tell a coherent story about program performance.
• You have a growth mindset and are committed to ongoing learning, both for yourself and for the teams you enable.

Nice to have

• Experience in the mental healthcare or behavioral health sector, or a deep interest in the mission of improving access to care.
• Background in coaching or training adult learners in a professional setting.
• Familiarity with compliance and regulatory considerations in hiring and employment law.
• Experience with data visualization tools or dashboarding platforms to communicate program impact.

Practical notes

This is a full-time remote role based in the United States. 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. Compensation details are provided for transparency and should be considered alongside the base offer package, which may include benefits such as medical, dental, and vision coverage, as well as paid time off and retirement planning options. There may be additional eligibility requirements and plan terms that apply.