Lead AI Engineer

Founded in 2019 and headquartered in Pittsburgh, PA, Free Market Health supports forward-thinking payers and specialty pharmacies of all sizes who need to operate in a complex and opaque market. We empower all stakeholders to optimize resources and maximize opportunities while focusing on the most important stakeholder of all: the patient.

Overview

We are looking for a hands-on and visionary

Lead AI Engineer

to drive the development, deployment, and scaling of AI capabilities across our platform. In this role, you will lead a small but growing team of AI engineers, shaping the roadmap, setting best practices, and ensuring the delivery of production-grade, high-impact AI solutions. You will serve as a bridge between technical implementation and business value, working closely with engineering leadership, product teams, and domain experts.

This role requires a deep understanding of AI/ML systems, strong architectural instincts, and a passion for mentoring and growing talent. You will help us navigate the evolving AI landscape and translate promising opportunities into scalable, real-world solutions that improve patient outcomes and drive our mission forward.

Specifics

The responsibilities for this role include, but are not limited to:

AI Strategy & Technical Leadership • Define and refine our AI engineering strategy in alignment with business goals and product opportunities. • Design and guide the implementation of end-to-end AI/ML pipelines, including data ingestion, model training, deployment, and monitoring. • Stay current with industry trends in AI/ML and evaluate their potential for application in our healthcare platform.

Team Leadership & Mentorship • Lead, mentor, and support a team of AI engineers, including direct supervision of junior AI engineers. • Establish engineering best practices for AI development, including coding standards, peer reviews, and model governance. • Foster a collaborative, feedback-driven team culture rooted in our company values: integrity, grit, collaboration, and adaptability.

Cross-functional Collaboration • Work closely with product management, data engineering, domain experts, and software engineers to define problem statements and deliver AI-powered features. • Translate business needs into actionable technical approaches that consider data availability, ethical implications, and operational constraints. • Communicate clearly with both technical and non-technical stakeholders to ensure alignment and transparency.

Productionization & MLOps • Own the architecture and scalability of deployed AI models in cloud environments. • Implement monitoring and retraining workflows to ensure long-term reliability and performance of AI solutions. • Contribute to infrastructure decisions related to model training environments, deployment tools, and experimentation platforms.

Requirements

Education • Bachelor's or Master's degree in Computer Science, Data Science, Engineering, or a related field. PhD is a plus.

Experience • 6+ years of experience working in AI/ML roles, with 2+ years of experience in a technical leadership position. • Proven track record of developing and deploying machine learning systems into production environments. • Experience leading cross-functional efforts and mentoring junior engineers.

Technical Skills • Advanced proficiency in Python and core machine learning libraries (TensorFlow, PyTorch, Scikit-learn, etc.). • Deep understanding of applied ML techniques including NLP, classification, prediction, and time-series analysis. • Hands-on experience working with Generative AI models (e.g. GPT, LLaMA, Claude), including prompt engineering, fine-tuning, and integrating GenAI into production applications. • Strong grasp of MLOps principles and tools for model lifecycle management (e.g., MLflow, SageMaker, Vertex AI). • Experience with cloud platforms (AWS, Azure, or GCP) and containerization (Docker, Kubernetes). • Solid grounding in algorithms, data structures, and applied mathematics.

Soft Skills • Demonstrated ability to communicate technical concepts clearly across audiences. • Strong sense of ownership and accountability in both individual and team contributions. • Passion for growing talent and building an inclusive, learning-focused team culture.

Preferred • Experience with healthcare, real-world data (e.g., claims, EMR), or regulated environments (e.g., HIPAA compliance). • Familiarity with responsible AI practices, model explainability, and ethical considerations in AI design. • Experience integrating AI features into large-scale, distributed systems.

What We Offer • Opportunity to lead AI efforts in a mission-driven, healthcare-focused technology company. • A collaborative, expert-driven team environment focused on impact, not ego. • A role where you can influence both strategic direction and technical implementation. • Access to modern cloud infrastructure and the autonomy to shape AI systems that matter.