Head of AI Transformation

Head of AI Transformation

Employment Type:Full-timeContract Type:Independent Contractor AgreementLocation:100% Remote

About the Role

We are seeking aHead of AI Transformationto embed within our portfolio companies and fundamentally transform how they operate through AI.

This is abuilder-operator rolefor 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 spansB2B 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 throughadoption, efficiency gains, and P&L impact, rather than technical sophistication alone.

You will work directly withManaging 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 isself-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 of20+ 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, includingRAG 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, includinghours 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 inComputer Science, Data Science, Information Systems, or a related field preferred.
* 3–6 years of experiencein 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 ofbuilding and deploying working systems, not just producing strategy decks.
* 2+ years of hands-on experienceshipping AI and automation solutions into live business environments.
* Strong proficiency inPython 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 diagnos