Head of AI Engineering & Enablement

The Head of AI Engineering & Enablement role is seeking an executive-level professional to define and scale AI adoption across a rapidly growing healthcare technology organization. Key responsibilities include:

1. Lead the strategy, development, and adoption of AI solutions that improve internal operations and organizational efficiency.
2. Partner with executive leadership and functional stakeholders to identify, prioritize, and execute AI opportunities that create measurable operational impact.
3. Develop and maintain an AI opportunity roadmap based on business value, feasibility, return on investment, and strategic priorities.
4. Re-engineer existing workflows and operating processes before applying automation to ensure AI solutions improve how work is performed.
5. Design, build, deploy, and maintain high-value internal AI agents, automations, and intelligent workflows.
6. Build production-grade AI solutions with appropriate monitoring, evaluation methods, error handling, and continuous improvement processes.
7. Establish governance standards for AI usage, including security controls, data-handling practices, risk management frameworks, and compliance requirements.
8. Ensure AI solutions meet healthcare privacy and security expectations, including protection of sensitive information and regulated data.
9. Create enablement programs that help teams adopt AI effectively through training, templates, office hours, and practical resources.
10. Coach functional AI champions and promote broader AI fluency across technical and non-technical teams.
11. Stay current with emerging AI technologies, models, tools, and methodologies to continuously improve organizational capabilities.
12. Lead and mentor a small engineering team while maintaining hands-on involvement in technical delivery.

Requirements include:

• Experience building production AI systems, improving operational processes, and driving adoption across complex organizations.
• Strong hands-on engineering background with the ability to design, build, and ship production systems.
• Deep experience developing and deploying AI solutions, including multi-agent systems, RAG architectures, LLM workflows, and AI-powered automation.
• Experience building integrations with enterprise systems, APIs, knowledge platforms, and data sources.
• Strong understanding of agent frameworks, MCP servers, retrieval strategies, and AI orchestration patterns.
• Experience working in healthcare, HIPAA-regulated environments, or similarly regulated industries with strict data privacy requirements.
• Proven ability to identify operational inefficiencies and translate business workflows into scalable technology solutions.
• Strong process re-engineering mindset with the ability to improve systems before automating them.
• Demonstrated experience driving AI adoption and behavioral change across non-technical teams.
• Experience leading and developing small engineering teams while maintaining hands-on involvement.
• Excellent communication skills with the ability to collaborate with executives, business leaders, and technical teams.
• Strong judgment, strategic thinking, and ability to operate effectively in ambiguous, fast-moving environments.

Benefits include:

• Competitive compensation range of approximately $224,000-$256,000 USD annually for the national average pay zone.
• Additional variable compensation opportunities and a comprehensive benefits package.
• A remote-first work environment with flexibility to work from home.
• Healthcare benefits and wellness resources for eligible employees.
• Home office support and technology discounts.
• Wellness programs, fitness resources, and employee assistance support.
• Opportunities to work on high-impact AI initiatives transforming healthcare operations.
• A collaborative culture focused on innovation, ownership, continuous improvement, and meaningful impact.
• Professional growth opportunities within a fast-moving technology organization.