AI Enablement Lead

Greenwood Project

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

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

and

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

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—breaking barriers and building a more inclusive financial industry.

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 reports directly to the CEO.

If you live and breathe AI—always testing the latest models, building agents for fun, 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.

This is a 6-month W-2 contract position with the potential to convert to a full-time permanent role. You'll own AI enablement across the entire organization: training staff to build and manage AI agents, standing up infrastructure, and shaping how our Scholars develop AI fluency that prepares them for the employment landscape two to three years from now.

Our vision: every staff member with Cursor on their desk managing 2–3 AI agents. Every Scholar graduating able to 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, 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 AI curriculum for our Scholars alongside coaches with deep expertise in investment banking, fintech, and sales
• Clear path to a permanent role with the opportunity to define what the position becomes long-term
• Mission-driven impact: every system you build contributes to creating $45 million in economic mobility for underrepresented students

Key Responsibilities

Staff AI Enablement (50% of your time):

• Train and coach every staff member to become a confident AI user—meeting people where they are and building skills progressively from basic prompting through agent management
• Serve as the go-to resource when team members hit a wall: debugging errors, troubleshooting workflows, helping people push through the learning curve
• Design and facilitate AI training sessions, office hours, and workshops that 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
• Track adoption metrics and celebrate wins to build momentum and reduce resistance to change

Technical Infrastructure & Systems (30% of your time):

• Assess the current tech stack (HubSpot, Monday.com, Microsoft Teams, Brightspace LMS) and identify high-impact AI integration opportunities
• Stand up and configure AI tools, agent frameworks, and workflows the team can use and maintain independently
• Build reusable templates, prompts, and agent architectures staff can customize
• Ensure AI systems are secure, well-documented, and maintainable—no black boxes
• Stay current on AI developments and evaluate new tools and approaches continuously
• Provide strategic recommendations to the CEO on technology investments 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 curriculum across all three Academies (Investment Banking, Fintech, Sales & Relationship Management)
• Help coaches design AI-powered projects that develop Scholars' ability to manage agents, interrogate outputs, and collaborate with AI strategically
• Support the vision of Scholars graduating with practical AI skills that give them a competitive edge in financial services recruiting
• Develop training materials 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

Qualifications Required

Multiple studies show that BIPOC and candidates from underrepresented populations are less likely to apply unless they meet every qualification. Greenwood Project is committed to finding the best candidate for the job—we strongly encourage you to apply even if you don't meet every qualification below.

Technical Foundation:

• 2–5 years of experience working with AI/ML tools or platforms in a professional setting
• Ability to write and debug code (Python, JavaScript, or similar) to build agents, configure APIs, and troubleshoot integrations—comfortable in a terminal
• Hands-on experience with LLMs (Claude, GPT, etc.), coding assistants (Cursor, Copilot), agent frameworks, and workflow automation
• Understanding of how AI systems work at a conceptual level—enough to explain why a prompt isn't working to a non-technical colleague
• Familiarity with CRM, LMS, and project management platforms (HubSpot, Monday.com, or similar is a plus)

Teaching & Communication:

• Ability to translate complex technical concepts into plain language—exciting, not intimidating
• Patience and empathy for learners at all comfort levels, with the ability to push people productively
• Strong written communication skills for documentation, training materials, and organizational communications
• Experience in training or enabling non-technical teams to adopt new technology

Mindset:

• Genuinely fascinated by AI—reading the research, testing the tools, thinking about implications before anyone asks
• Intellectually curious with a bias toward action: you experiment and form your own views
• Comfortable with ambiguity and building where the playbook doesn't exist yet
• Self-directed with strong follow-through
• Growth mindset: your success is measured by how capable the team becomes
• Mission alignment: you care about economic mobility, equity, and opportunity for underrepresented students

What Success Looks Like

By 90 Days:

• Completed assessment of current tech stack and AI readiness across the team
• AI tools and infrastructure selected, configured, and ready for adoption
• First wave of staff training delivered; every team member has a clear AI adoption pathway and personal learning plan
• Initial relationships built with Academy coaches

By 6 Months:

• Every staff member actively using AI tools and progressing toward managing 2–3 agents
• AI infrastructure stable, documented, and maintainable by the team—not dependent on one person
• Scholar-facing AI curriculum framework developed and initial modules integrated into Academy programming
• Clear recommendations delivered to CEO on long-term AI strategy and technology investments
• Coaches equipped to design AI-integrated projects within their specializations

Work Location Remote-friendly. Greenwood Project is headquartered in Chicago, IL; occasional travel may be requested but is not required.

Shared Values

• Cultural Competency: We build working knowledge of diverse identities, experiences, and history, consistently adapting our approach to the cultural context of the communities we serve.
• Influence and Impact: We learn about the working styles of others and adapt to maximize everyone's success.
• Strategic Thinking: We critically analyze inputs and create systems that are scalable and sustainable.
• Self-Direction: Our team operates with initiative and follow-through to build trust in each other.
• Balance: We value in-person collaboration and independent, flexible work through our hybrid schedule.
• Growth: We want your career to be satisfying long-term—we welcome learning, stretching, and growing.

Equal Employment Opportunity Policy The Greenwood Project is an equal opportunity employer.

Compensation and Benefits Base Salary: $95,000–$115,000 (annualized) Contract Term: 6-month W-2 contract with potential for conversion to full-time permanent role

This role offers a comprehensive benefits package including health care, dental and vision coverage, disability insurance, a 401(k) plan, and generous paid time off.

If you're the person who can't stop thinking about what AI makes possible—and you want to channel that energy into work that creates real economic mobility for underrepresented students—we want to hear from you.