AI Enablement Lead
About The Position
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. This is a 6-month W-2 contract position with the potential to convert to a full-time permanent role based on performance and organizational fit. 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 • Clear path to a permanent role with the opportunity to define what the position becomes long-term • Mission-driven impact: every system you build and every person you train contributes to creating $45 million in economic mobility for underrepresented students
Requirements
- 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)
- 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)
- 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
Nice To Haves
- Familiarity with CRM, LMS, and project management platforms (experience with HubSpot, Monday.com, or similar is a plus)
Responsibilities
- 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
- 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
- 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
Benefits
- This role offers a comprehensive benefits package that includes access to employee health care, dental and vision coverage, disability insurance, as well as a 401(k) plan and generous paid time off.
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What This Job Offers
Career Level
Mid Level
Education Level
No Education Listed
