Head of AI Engineering & Enablement

Role overview A player-coach leadership role owning AI engineering and enablement for the internal operations of a healthcare technology company scaling toward $300M+ in ARR. The hire will build alongside a small team of one to two engineers while partnering with the CEO, CFO, CPO, and functional leaders to re-engineer workflows, ship internal agents, and decouple growth from headcount. The focus is on how the company runs—not on customer-facing product AI—and on compounding leverage through shared patterns, governance, and broad adoption.

Responsibilities - Identify and prioritize where AI can drive the greatest efficiency and operating leverage, then audit and re-engineer business processes before automating them. - Build and maintain an AI Opportunity roadmap ranked by ROI, feasibility, and strategic impact in partnership with functional leaders. - Design and build high-value internal agents and automations, including multi-agent systems with hand-offs across workflow steps. - Own shared patterns for retrieval, agent design, and secure system-of-record connectivity across tools such as Gong, Salesforce, NetSuite, Snowflake, Slack, and Workato, including MCP servers and permission-aware access. - Build and maintain an organizational context layer—meeting capture, knowledge connectors, MCP servers, and permission-aware retrieval—that gives agents and people a single source of truth. - Define approved tools, data-handling rules, build standards, and a shared reference architecture for AI in partnership with Legal and Security, including HIPAA-compliant deployment, monitoring, a risk register, an acceptable use policy, and audit trails. - Enable functional teams through coaching, training, prompt libraries, office hours, and ready-to-use templates that scale adoption beyond the central team. - Take ownership from rapid prototyping through production-grade deployment, including monitoring, evaluation frameworks, error handling, and iteration based on real usage.

Requirements - Demonstrated track record as a hands-on AI or software engineering leader who can ship code while leading others. - Deep engineering and applied AI skill paired with strong business judgment and an outcomes-driven mindset. - Experience designing agents, automations, and integrations across enterprise systems, including multi-agent orchestration. - Familiarity with retrieval patterns, MCP servers, API integrations, and permission-aware access to systems of record. - Ability to partner with senior executives and functional leaders to find, prioritize, and deliver high-impact use cases. - Experience standing up governance artifacts such as risk registers, acceptable use policies, and audit trail standards. - Comfort owning the full lifecycle from prototype to production, including monitoring and evaluation.

Nice to have - Experience operating inside a healthcare or other highly regulated environment, particularly with HIPAA, PHI, and strict data privacy requirements.

Benefits and work setup - U.S. perks include healthcare benefits plus a Dell discount for home office equipment, Gympass for fitness and wellness, and a Telus Employee Assistance Program for mental health and everyday support. - Costa Rica perks include a wellness and childcare subsidy, a university/education discount, Gympass, and a Telus Employee Assistance Program. - Equal opportunity employer with attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status; California applicants are directed to a separate supplemental privacy notice.