AI Enablement Lead

greenwoodproject; Chicago (IL); On-site; USD 150,000 - 190,000; Full time

Job summary

Greenwood Project in Chicago is seeking an AI Enablement Lead to transform how we work, how our Scholars learn, and how our organization scales through strategic AI adoption.

You will own AI enablement across the organization—training staff to manage AI agents, building infrastructure, and shaping a curriculum that prepares Scholars for the job market in the next few years. Reporting to the CEO, you’ll drive impact and growth.

Qualifications

• Experience leading cross-functional AI initiatives.
• Strong ability to translate AI concepts into scalable programs.
• Excellent communication with executives and coaches.

Responsibilities

• Own AI enablement across the organization, from ops to Scholar training.
• Train staff to build and manage AI agents and workflows.
• Stand up AI infrastructure and governance for scale.
• Shape the AI curriculum for Scholars to improve future job readiness.

Skills

AI strategy

Team leadership

Curriculum design

Education

Bachelor's in CS/AI

Tools

ML frameworks

Job description

Greenwood Project

The Greenwood Project was founded in 2016 based on two core principles:

"Students can't be what they can't see"

"There is no lack of talent, only a lack of opportunity."

GP's mission is bold, essential and long overdue. We are dedicated to creating opportunities for qualified Black and Latino college students to attain high-trajectory careers in financial services through rigorous training and internships. At Greenwood Project, we don't just talk about change; we are the catalyst for it, breaking barriers and building a more inclusive and diverse financial industry. Our people are the foundation that allows us to achieve our ambitious goals. Becoming part of the Greenwood Project team means joining a group of driven, passionate and intellectually curious individuals. To work here is to be crucial to the organization’s success.

AI Enablement Lead

Ready to build the AI future of a mission-driven organization from the ground up? We're seeking an AI Enablement Lead to transform how our team works, how our Scholars learn, and how our organization scales—all through strategic AI adoption. This position will report directly to the CEO.

If you live and breathe AI—if you're the person who's always testing the latest models, building agents for fun, and explaining to friends why this moment matters—this role lets you channel that passion into work that creates real economic mobility for Black and Latino college students.

You'll own AI enablement across the entire organization: training staff to build and manage their own AI agents, standing up infrastructure, and ultimately shaping how our Scholars develop AI fluency that prepares them for the employment landscape two to three years from now.

Our vision is bold: every staff member with Cursor on their desk, managing 2-3 AI agents that drive real productivity gains. Every Scholar graduating with the ability to manage multiple agents and collaborate with AI at a level most entry-level professionals won't reach for years. You'll be the person who makes that happen.

What Makes This Unique:

• Own AI strategy for an entire organization - not a single product team or department, but everything from operations to Scholar training
• Direct reporting line to the CEO with visibility across every function
• Build from the ground up: we're at the Cowork/Claude stage and ready to accelerate toward Cursor and custom agents
• Shape the AI curriculum for our Scholars, working alongside coaches with deep industry expertise in investment banking, fintech, and sales
• Mission-driven impact: every system you build and every person you train contributes to creating $45 million in economic mobility for underrepresented students