Job Overview
I am an entrepreneur and CEO of an education-focused company looking for an experienced AI practitioner to work directly with me approximately four half-days per month in the Indianapolis area.
This is not a traditional training position, consulting engagement, or outsourced developer role.
I am looking for someone who can help me rapidly increase my AI expertise by teaching me while we build real solutions together.
My primary goal is to become a significantly more AI-capable CEO. I want to understand AI deeply enough to identify opportunities, build practical solutions, evaluate technical decisions, work intelligently with developers, and eventually teach educational leaders how they can use AI to operate more effectively.
Our sessions will be highly applied. Rather than spending hours discussing concepts or watching demonstrations, we will identify real business problems and build solutions together.
Initial projects will likely include:
- Internal AI automations that increase operational efficiency within my company.
- Working AI agents that can perform or support multi-step business processes.
- Simple software applications that solve real problems for our team or customers.
- Prototypes and experiments that may eventually influence larger products we develop.
What I Want to Learn
I am already a frequent AI user. I am not looking for an introduction to ChatGPT or basic prompting.
I want someone who can help me progress from being an advanced AI user into someone who understands how AI systems are actually designed and built.
Areas of learning may include:
- AI Agents
- What agents actually are and when they should be used.
- How agents differ from prompts, workflows, and traditional automation.
- How agents use tools, memory, context, APIs, and external information.
- How to design, build, test, and improve useful agents.
- How to determine when an agent is unnecessarily complicated.
- Workflow and Business Automation
- Identifying repetitive work that should be automated.
- Mapping business processes before automating them.
- Using platforms such as n8n, Make, Zapier, or similar tools.
- Connecting AI to existing business systems.
- Designing human approval and oversight into automated processes.
- Coding and Application Development
- Learning the fundamentals of coding through practical projects.
- Understanding Python, JavaScript, APIs, databases, and other concepts at a useful executive-builder level.
- Using AI coding tools to accelerate development.
- Building simple internal tools and applications.
- Understanding how modern AI applications move from idea to prototype to production.
- AI Product Development
- Translating a business problem into an AI product concept.
- Understanding architecture decisions without needing to become a senior software engineer.
- Evaluating technology stacks and development approaches.
- Understanding build-versus-buy decisions.
- Estimating complexity, development effort, ongoing maintenance, and cost.
- Becoming a much stronger buyer and manager of outside AI development.
- AI Systems and Architecture
- APIs and model integrations.
- Retrieval-Augmented Generation and knowledge bases.
- Structured and unstructured data.
- Model selection.
- Context management.
- Tool calling.
- Agent architecture.
- Data flow between systems.
- Reliability and Evaluation
- Determining what a good AI output actually looks like.
- Testing agents and AI applications.
- Identifying failure points.
- Creating evaluation criteria.
- Understanding hallucinations and reliability issues.
- Building appropriate guardrails and human oversight.
- AI Strategy
- Identifying where AI can create meaningful leverage in a business.
- Distinguishing valuable AI opportunities from technology hype.
- Evaluating emerging AI tools and platforms.
- Understanding how AI may change organizational structures and workflows.
- Identifying opportunities that I may not currently know enough to recognize.
The Bigger Objective
I lead a company that works extensively with school and district leaders.
One of my longer-term goals is to translate what I learn into practical ways educational leaders can use AI to improve strategy, communication, productivity, decision-making, and operational efficiency.
For that reason, I am particularly interested in someone who can help me develop both:
Technical understanding: How AI systems actually work and are built.
Executive understanding: Where AI creates value, what should be automated, what should remain human-led, and how organizations should think about adopting AI responsibly.
I am also involved in developing AI-enabled products. Increasing my technical fluency will allow me to make significantly better decisions when working with developers, evaluating product ideas, setting priorities, and determining what should and should not be built.
How We Will Work
This role will be intentionally different from a normal training engagement.
We will generally meet four half-days per month, in person, in the Indianapolis area.
I am not interested in virtual sessions.
During our time together, I want us sitting beside each other and actually building.
A typical session might involve:
- Selecting a real business problem.
- Mapping how the work currently happens.
- Determining whether the best solution is prompting, automation, a workflow, an agent, or an application.
- Designing the solution together.
- Building the solution together.
- Testing and troubleshooting it.
- Helping me understand why it works.
- Having me reproduce or modify parts of the system myself.
- Discussing how the underlying concept could apply to other business or educational leadership problems.
The objective is not simply for you to build something for me.
The objective is for my capability to increase every month.
Who I Am Looking For
The ideal person is an experienced AI practitioner who has actually built useful AI systems.
You may be an:
- AI engineer
- AI automation consultant
- Software engineer working heavily with AI
- AI product builder
- Technical founder
- Applied AI consultant
- Automation specialist with strong AI expertise
Formal teaching experience is not required.
However, you must be able to explain technical concepts clearly to a highly engaged non-engineer who wants to understand how things actually work.
Strong Candidates Will Have Experience With Several of the Following
- Building AI agents
- AI APIs
- OpenAI, Anthropic, Gemini, or other major model platforms
- Python and/or JavaScript
- AI-assisted coding environments
- n8n, Make, Zapier, or similar automation tools
- APIs and webhooks
- Databases
- RAG and knowledge systems
- Agent frameworks
- Application prototyping
- AI evaluation and testing
- AI product architecture
- Deploying practical AI solutions inside businesses
I am less concerned with knowing every specific platform than I am with finding someone who understands the principles underneath the tools.
The Person I Do Not Want
This will probably not be a good fit if your AI expertise primarily consists of:
- Prompt engineering
- ChatGPT training
- Selling AI courses
- Creating demonstrations without deploying real systems
- No-code automation without understanding the technology underneath it
- Software development without meaningful AI experience
I want someone who builds.
What Success Looks Like
After working together for 6 to 12 months, I should be substantially different as a CEO.
I should be able to:
- Identify valuable AI opportunities inside my business.
- Design basic AI workflows and agents.
- Build or modify simple AI applications.
- Understand enough code to work intelligently with AI-assisted development.
- Understand APIs, data, models, agents, workflows, and application architecture at a practical level.
- Evaluate whether an AI solution is well designed.
- Ask developers significantly better questions.
- Make stronger decisions about AI product development.
- Recognize unnecessary technical complexity.
- Understand AI well enough to teach practical applications to other organizational leaders.
- Develop prototypes that could become internal systems, client-facing solutions, or future products.
- Continue learning independently because I understand the underlying concepts rather than simply knowing how to use individual tools.
Compensation
Compensation is flexible and will be based on the level of expertise and value you can bring.
I am willing to pay a premium for the right person.
This is not about finding the least expensive trainer. I am looking for someone whose experience can meaningfully accelerate my learning and help me avoid spending years trying to develop this knowledge on my own.
The expected commitment is approximately four half-days per month, with the possibility that the relationship evolves as projects and opportunities develop.
Location Requirement
You must be able to regularly meet in person in the Indianapolis, Indiana area.
Please do not apply if you are only available virtually.
Face-to-face, hands-on collaboration is a fundamental part of this position.
How to Apply
Rather than sending only a traditional resume, please include a brief response addressing the following:
- Describe two or three AI agents, automations, or applications you have personally built.
- What parts of those systems did you personally design or develop?
- What AI development tools and platforms do you currently use most?
- Give an example of a business process you believe should be automated and one that you believe should not.
- How would you teach a non-programmer to begin building AI applications?
- If you had four half-days per month with a CEO for one year, how would you structure the learning experience?
- What do you believe business leaders misunderstand most about AI right now?
- What would you want me to be capable of doing independently after six months?
- Are you able to consistently meet in person in the Indianapolis area?
- What compensation structure would make this engagement worthwhile for you?
Please include links to projects, GitHub repositories, applications, demos, case studies, or other examples of your work when appropriate.
I am particularly interested in candidates who can look at the goals described above and say, “There are several things you haven't mentioned that you also need to understand.”
Pay: From $2,000.00 per month
Work Location: Hybrid remote in Indianapolis, IN 46202
