AI Enablement Lead

AI Enablement Lead

Department: Corporate

Employment Type: Full Time

Location: Chicago, IL

Compensation: $95,000 - $115,000 / year

Greenwood Project was founded in 2016 to create opportunities for qualified Black and Latino college students, fostering high‑trajectory careers in financial services through rigorous training and internships. The organization is dedicated to building a more inclusive and diverse financial industry.

We are 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. The role reports directly to the CEO and involves training staff, building infrastructure, and shaping AI fluency for scholars.

Staff AI Enablement (50% of your time)

• Train and coach every staff member to become a confident AI user, progressing from basic prompting to agent management.
• Serve as the go‑to resource for troubleshooting agent errors and optimizing workflows.
• Design and facilitate structured AI training sessions, office hours, and hands‑on workshops to build organization‑wide capability.
• Support each team member in identifying, building, and deploying 2–3 AI agents aligned with their role by year‑end.
• Guide the team’s progression from Claude and Cowork through Cursor and custom agent development, creating a clear adoption pathway.
• Track adoption metrics and celebrate wins to build momentum and reduce resistance to change.

Technical Infrastructure & Systems (30% of your time)

• Assess the current technology stack (Hub Spot, , Microsoft Teams, Brightspace LMS) and identify high‑impact AI integration opportunities.
• Stand up and configure AI tools, agent frameworks, and workflows that the team can use and maintain independently.
• Build reusable templates, prompts, and agent architectures that staff can customize for their own needs.
• Ensure AI systems are secure, well‑documented, and maintainable.
• Stay current on AI developments and evaluate new tools, models, and approaches that could benefit the organization.
• Provide strategic recommendations to the CEO on technology investments, platform decisions, and AI roadmap priorities.

Scholar AI Curriculum Development (20% of your time)

• Partner with the Director of Programs and Academy coaches to integrate AI fluency into the existing curriculum across all three Academies.
• Help coaches design AI‑powered projects and capstone experiences that develop Scholars’ ability to manage agents and collaborate strategically with AI.
• Support the vision of Scholars graduating with practical AI skills that give them a competitive edge in financial services recruiting.
• Develop training materials and frameworks that coaches can deliver independently, building sustainable AI instruction capacity.
• Stay connected to how financial services firms are adopting AI so Scholar training reflects real employer expectations.

We encourage candidates who may not meet every single qualification to apply.

Technical Foundation

• 2–5 years of experience working with AI/ML tools, platforms, or applications in a professional setting.
• Ability to write and debug code (Python, JavaScript, or similar) sufficient to build agents and troubleshoot integrations.
• Hands‑on experience with current AI tools and platforms: LLMs (Claude, GPT, etc.), coding assistants (Cursor, Copilot), agent frameworks, and workflow automation.
• Understanding of how AI systems work at a conceptual level.
• Familiarity with CRM, LMS, and project management platforms (Hub Spot, , or similar).

Teaching & Communication

• Exceptional ability to translate complex technical concepts into plain language.
• Patience and empathy for learners at different comfort levels with technology.
• Strong written communication skills for creating documentation, training materials, and organizational communications about AI strategy.
• Experience training, coaching, or enabling non‑technical teams to adopt new technology.

Mindset

• Genuinely fascinated by AI and its future, actively researching and experimenting.
• Intellectually curious with a bias toward action.
• Comfortable with ambiguity, building in a lean organization.
• Self‑directed with strong…