Head of AI

We’re hiring a Head of AI to lead the vision, strategy, and execution of EnrollHere’s AI initiatives. This is a high-impact leadership role that blends strategic foresight with hands-on technical expertise to build and scale AI-driven solutions that improve compliance, agent performance, and operational efficiency.

You’ll develop advanced AI/ML models, oversee integrations into our platforms, and ensure solutions align with regulatory requirements and business objectives. Partnering with Data, Product, and Engineering, you’ll set the roadmap, guide technical execution, and build a world-class AI team.

Responsibilities

• Own and evolve EnrollHere’s AI vision, strategy, and multi-year roadmap.
• Lead design, training, and deployment of AI/ML models for compliance, lead scoring, call routing, and real-time agent assistance.
• Oversee prompt engineering, LLM fine-tuning, and integrations into systems.
• Establish best practices for model evaluation, monitoring, and continuous improvement.
• Collaborate with teams to ensure clean, high-quality datasets for model training.
• Ensure compliance with HIPAA, SOC 2, and other applicable regulations.
• Build, mentor, and manage a high-performing AI team.
• Evaluate and manage AI technology partners.
• Define KPIs for AI initiatives and communicate outcomes to leadership.

Requirements

Proven track record building, deploying, and scaling AI systems in production.

8+ years in data science, ML, or AI engineering; 3+ years in leadership.

Expertise in LLMs, NLP, and applied ML in enterprise contexts.

Experience in regulated industries such as healthcare, insurance, or financial services.

Proficiency with TensorFlow, PyTorch, Databricks, and Snowflake.

Familiarity with AWS, Azure, or GCP and MLOps practices.

Excellent cross-functional communication and leadership skills.

Benefits

We believe in taking care of our team, which is why we offer a comprehensive benefits package that supports your health, wellness, and future:

• Medical: 4 United Healthcare medical plans (including an HSA option)
• Dental: 3 dental plans (Aetna and MetLife)
• Vision: 2 Aetna vision plans
• Wellness & Mental Health: 5 additional Medical Plus benefits, including telehealth support and an annual Talkspace subscription
• Ancillary Coverage: 4 ancillary plans and supplemental life insurance
• Retirement: 401(k) with a 4% match (after a 90-day exclusionary period)
• PTO & Flexibility: Generous PTO and remote work support
• Growth: Learning stipends and opportunities for professional development