AI Enablement Lead

Job Description

Job Description

Description

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.”

 

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

Key Responsibilities

Staff AI Enablement (50% of your time):

•           Train and coach every staff member to become a confident, capable AI user—meeting people where they are and building their skills progressively from basic prompting through agent management

•           Serve as the go-to resource when team members hit a wall: debugging agent errors, troubleshooting workflows, and helping people push through the learning curve

•           Design and facilitate structured AI training sessions, office hours, and hands-on 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, ensuring these agents deliver real productivity gains

•           Guide the team’s progression from Claude and Cowork through Cursor and custom agent development, creating a clear adoption pathway that doesn’t overwhelm

•           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 (HubSpot, Monday.com, 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—no black boxes that only you can operate

•           Stay current on AI developments and continuously 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 (Investment Banking, Fintech, Sales & Relationship Management)

•           Help coaches design AI-powered projects and capstone experiences 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—not just awareness, but operational proficiency

•           Develop training materials and frameworks that coaches can deliver independently, building sustainable AI instruction capacity within the program team

•           Stay connected to how financial services firms are actually adopting AI so Scholar training reflects real employer expectations, not theoretical concepts

Qualifications

Qualifications Required
A note to potential candidates: Multiple studies have shown that BIPOC and other candidates from marginalized populations are less likely to apply for jobs unless they believe they meet every single one of the qualifications in a job description. Greenwood Project is committed to building a diverse, equitable, and inclusive organization and finding the best candidate for the job. We strongly encourage interested individuals to apply, even if they don’t believe they meet all of the qualifications described below.

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, configure APIs, and troubleshoot integrations—you don’t need to be a software engineer, but you need to be comfortable in a terminal

•           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—enough to explain to a non-technical team member why a prompt isn’t working or how an agent should be structured

•           Familiarity with CRM, LMS, and project management platforms (experience with HubSpot, Monday.com, or similar is a plus)

Teaching & Communication:

•           Exceptional ability to translate complex technical concepts into plain language—you can explain agents to someone who’s never opened a terminal and make it feel exciting, not intimidating

•           Patience and empathy for learners at different comfort levels with technology, paired with the ability to push people past their comfort zones productively

•           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 (formal teaching, corporate training, or similar)

Mindset:

•           Genuinely fascinated by AI and where it’s headed—you’re reading the research, testing the tools, and thinking about implications before anyone asks you to

•           Intellectually curious with a bias toward action: you don’t just follow AI trends, you experiment with them and form your own views

•           Comfortable with ambiguity and building in an environment where the playbook doesn’t exist yet—you’ll be creating it

•           Self-directed with strong follow-through: in a lean organization, you’ll need to manage your own time, priorities, and deliverables

•           Growth mindset with a genuine interest in helping others develop—your success is measured by how capable the team becomes, not just what you build yourself

•           Mission alignment: you care about economic mobility, equity, and creating 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 team adoption

•           First wave of staff training sessions delivered; every team member has a clear understanding of the AI adoption pathway and their personal learning plan

•           Initial relationships built with Academy coaches to understand curriculum integration opportunities

By 6 Months:

•           Every staff member is actively using AI tools in their daily work and progressing toward managing 2–3 agents aligned with their role

•           AI infrastructure is stable, documented, and maintainable by the team—not dependent on a single person

•           Scholar-facing AI curriculum framework developed, and initial modules integrated into Academy programming

•           Clear recommendations delivered to CEO on long-term AI strategy, technology investments, and organizational readiness for next phase

•           Coaches equipped with knowledge and tools to design AI-integrated projects within their Academy specializations

Benefits

Work Location: This role is based in Chicago, IL, with flexibility for remote work for the right candidate

Salary and Benefits:  The salary range for this role is  $95,000–$115,000 annually, commensurate with experience. This role offers a comprehensive benefits package that includes employee health care, dental and vision coverage, disability insurance, 401(k) plan, and generous paid time off. 

Shared Values

•           Cultural Competency: All team members strive to build a working knowledge of the historical, social, and economic history of this country with a particular value for diverse identities, ideas, and experiences. As team members, we consistently work to acquire and apply cultural knowledge and adapt to the cultural context of various communities. We are reflective and often think about the impact of our actions, words, and thoughts on various components of their and others’ intersectional lines of identity. We strive to self-monitor our various layers of privilege and push the organization to be the strongest collection of voices possible.

•           Influence and Impact: We value learning about the working styles and preferences of others and strive to adapt our approach to maximize the success of everyone on the team.

•           Strategic Thinking: We critically analyze inputs and think through the long-term outputs of the organization, working to create systems and structures that are scalable and sustainable.

•           Self-Direction: Our team members operate with both initiative and follow-through to ensure that we can operate in ways that build trust in each other.

•           Balance: We value in-person collaboration and independent, flexible work. That is why we have a hybrid schedule, with most associates finding a balance between office and home.

•           Growth: We want your career to be satisfying for the long term. If you want to try a new project or attend a meeting with another group, we welcome it. We want you to learn, stretch, and grow as much as you want.

Equal Employment Opportunity Policy

The Greenwood Project is an equal opportunity employer and does not discriminate on the basis of race, color, national origin, sex, sexual orientation, gender identity, disability, age, religion, ancestry, marital status, familial status, or any other legally protected classification federally or in the State of Illinois. The Greenwood Project does not discriminate in its activities, educational programs, hiring practices, or employment practices as required by Title VI, IX, and Section 504.

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