About CoverRight

CoverRight is on a mission to make Medicare, and retiree health-related-finances transparent and accessible. We’re building technology to empower older adults to confidently navigate their healthcare options through personalized guidance and modern digital experiences. We’re a fast-growing, venture-backed company blending human expertise with AI-driven technology to transform how people make critical healthcare decisions.

About the Role

We’re seeking a versatile AI/ML Engineer to design, develop, and deploy both Generative AI and traditional machine learning solutions that power CoverRight’s products and operations. This is a highly cross-functional role where you’ll work closely with the Head of Product & Engineering, as well as our data and operations teams, to bring intelligence and automation to every part of the business. You’ll help shape the foundation of how AI is used across the company — from personalized recommendations and lead optimization to intelligent voice/chat agents and knowledge retrieval systems.

What You’ll Do

Generative AI & Applied NLP Design, prototype, and deploy LLM-based applications for conversational agents, knowledge retrieval, and automation. Build retrieval-augmented generation (RAG) systems using vector databases and embedding models to surface accurate, context-aware responses. Fine-tune or prompt-engineer LLMs (e.g., OpenAI, Anthropic, Mistral, etc.) for specific CoverRight use cases. Develop tools to summarize documents, extract structured data, and assist internal teams with AI copilots.

Traditional ML & Data Science Develop and maintain predictive models to optimize lead scoring, conversion prediction, and customer engagement. Build, test, and deploy classification, regression, and clustering models to drive product and operational insights. Design scalable data pipelines for training, evaluation, and monitoring of ML models in production. Partner with stakeholders to define metrics, improve data quality, and translate business problems into ML solutions.

Engineering & Infrastructure Implement APIs and backend services to integrate AI/ML models into product experiences. Maintain and monitor deployed models for performance, drift, and reliability. Evaluate emerging AI/ML tools, frameworks, and platforms to continuously improve our stack. Ensure data privacy, security, and compliance with HIPAA and PHI handling requirements.

What You’ll Bring 3+ years of hands-on experience in AI/ML engineering, applied ML, or data science. Proficiency in Python and ML frameworks such as PyTorch, TensorFlow, or scikit-learn. Strong experience with modern Generative AI tools (OpenAI API, LangChain, Hugging Face, or similar). Understanding of embeddings, vector databases (e.g., Pinecone, Weaviate, FAISS), and RAG architectures. Experience with building and deploying ML models on AWS, GCP, or Azure. Familiarity with data orchestration tools (Airflow, Prefect) and version control (Git). Knowledge of data warehousing, feature stores, and model monitoring best practices. Excellent communication skills — able to bridge technical depth with business understanding. (Bonus) Experience working with healthcare or insurance data, including HIPAA compliance considerations.

Why Join CoverRight Build AI systems that make finances and healthcare more human, transparent, and personalized. Shape the future of a growing AI-driven healthtech company. Work with a smart, mission-driven, and collaborative team. Competitive salary, equity, and benefits package. Remote-first environment with flexible hours and strong ownership culture.

Location This role can be done remotely from the U.S. or Canada. Preference for candidates who are based in one of our key hubs: NYC, Buffalo, or Toronto Our team operates on Eastern Time (EST), so availability during core business hours is important

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CoverRight - AI/ML Engineer