Head of AI Transformation

Employment Type: Full-time
Contract Type: Independent Contractor Agreement
Location: 100% Remote

About the Role

We are seeking a Head of AI Transformation to embed within our portfolio companies and fundamentally transform how they operate through AI.

This is a builder-operator role for someone who can enter a business, quickly diagnose its highest-leverage workflows, and design, build, and deploy enterprise-grade AI solutions that create measurable operational and financial impact.

Our portfolio spans B2B services, healthcare, education, industrial, consumer, and other sectors, meaning every deployment will present a different set of challenges and opportunities.

The ideal candidate is excited by the full AI technology stack—from data ingestion and retrieval to orchestration, automation, and intelligent agents—but measures success through adoption, efficiency gains, and P&L impact, rather than technical sophistication alone.

You will work directly with Managing Directors, portfolio CEOs, and frontline teams, owning projects from the initial diagnostic through implementation, adoption, and measurement.

This is a highly autonomous role suited to someone who is self-motivated, entrepreneurial, highly accountable, and comfortable operating in fast-paced and ambiguous environments.

Why Join Us?

Join a lean, high-performance team of operators and investors.
Work directly with CEOs and senior leadership to transform real businesses across multiple industries.
Help establish the AI operating standard across a growing portfolio of 20+ companies.
Prototype, deploy, and scale AI-powered solutions with measurable EBITDA impact.
Take significant ownership and influence the future direction of a rapidly scaling holding company.
Work across diverse industries, solving new and complex operational challenges.

Key Responsibilities

AI Transformation & Process Optimization

Embed within portfolio companies to map, diagnose, and redesign core business processes.
Identify high-impact workflows where AI and automation can generate meaningful operational and financial improvements.
Evaluate existing processes, systems, and data to identify opportunities for automation and AI adoption.
Identify, evaluate, and integrate AI and automation tools into day-to-day business operations.

AI & Automation Engineering

Design and develop LLM-powered solutions, including RAG pipelines, tool-using agents, and agentic workflows.
Architect data pipelines for the ingestion, transformation, and retrieval of structured and unstructured data.
Evaluate and integrate LLM frameworks, orchestration tools, and model providers into backend services and APIs.
Build practical AI systems capable of operating reliably within real-world business environments and handling edge cases.
Prototype and ship solutions directly, then work with portfolio engineers or contractors to harden, scale, and maintain successful implementations.

Adoption & Business Impact

Own AI initiatives from initial diagnosis through implementation and full adoption.
Train teams and drive consistent usage of newly implemented systems.
Develop playbooks, dashboards, and reusable toolkits that facilitate adoption across portfolio companies.
Track and communicate measurable impact, including hours saved, productivity improvements, revenue generated, and EBITDA impact.
Partner with deal teams, operating executives, and portfolio leadership to integrate operational data and identify additional opportunities.

Required Qualifications

Strong systems-thinking ability with the capacity to understand complex business processes and design scalable solutions.
Bachelor's degree in Computer Science, Data Science, Information Systems, or a related field preferred.
3–6 years of experience in forward-deployed engineering, AI transformation consulting, automation engineering, BizOps, technology consulting, or a similar environment.
Experience comparable to a forward-deployed engineer at an AI-native company or a transformation consultant who is capable of building and deploying working systems, not just producing strategy decks.
2+ years of hands-on experience shipping AI and automation solutions into live business environments.
Strong proficiency in Python and SQL, with experience using modern AI/ML tooling.
Demonstrated intellectual curiosity, creative problem-solving, and adaptability.
Strong entrepreneurial mindset with a willingness to experiment, iterate, and learn quickly.
Highly organized with the ability to independently manage and execute complex cross-functional initiatives.
Excellent written and verbal communication skills.
Comfortable communicating with and earning the trust of non-technical stakeholders, from frontline operators and business owners to CTOs.
Ability to manage multiple priorities and perform effectively under pressure.
Willingness to travel and work onsite at portfolio companies during diagnostic and deployment sprints.

Preferred Qualifications

Experience with one or more of the following is highly desirable:

LLMs, RAG, embeddings, and vector databases, including OpenAI, Anthropic, ChromaDB, or Pinecone.
Agent frameworks and orchestration tools, including LangChain, LlamaIndex, or Pydantic.
Workflow automation and low-code platforms such as n8n, Zapier, and Retool.
Data engineering tools and infrastructure, including Airflow, dbt, Spark, cloud platforms, and Linux environments.
MLOps, AI evaluation, observability, monitoring, and AI system reliability.

Ideal Candidate

The ideal candidate is not simply an AI engineer or consultant—they are a business-minded builder.

You are someone who can walk into an unfamiliar company, understand how the business actually operates, identify where time and money are being lost, and determine where AI can create the greatest leverage.

You are equally comfortable talking to a CEO, mapping a workflow, writing Python, building an automation, deploying an AI agent, training a team, and measuring the resulting business impact.

Most importantly, you care about building solutions that people actually use and that produce measurable results.

Head of AI Transformation - 20937