Head of AI Engineering & Enablement
$224,000–$325,000 year
RemoteUnited States or Costa Rica
Job Summary
Audit and re-engineer business processes to identify high-impact efficiency opportunities before automating them. Design and build high-value internal agents, multi-agent systems, and automations using MCP servers, agent-to-agent orchestration, and API integrations across Gong, Salesforce, NetSuite, Snowflake, Slack, and Workato. Own the organizational context layer, including meeting capture, knowledge connectors, and permission-aware retrieval for a single source of truth. Define approved tools, data-handling rules, and a shared reference architecture in partnership with Legal and Security, ensuring full HIPAA compliance and strict adherence to PHI policies. Partner with functional leaders to coach AI owners, run enablement programs, and build on-ramps like role-specific training and prompt libraries to scale adoption. Manage the full lifecycle from rapid prototyping to production-grade deployment, including monitoring, evaluation frameworks, and error handling based on real usage data.
Required Qualifications
- 8+ years in software engineering, applied AI, or technical product roles
- Meaningful stretch spent hands-on and building in production — not directing from a distance
- An engineering background you still use. You can read and write code and ship production systems, not only manage people who do
- Deep applied AI experience designing and deploying multi-agents systems, RAG pipelines, agent-to-agent orchestrations, MCP servers, and API integrations into systems of record, and LLM-based workflows in production
- Hands-on experience shipping AI in a HIPAA-regulated or comparable environment — working within BAAs, maintaining audit trails, and keeping PHI out of non-covered tools
- A track record on operationally focused technology projects — workflow automation, systems integration, internal tooling — that demonstrably changed how a business runs
- Strong business acumen. You can sit with a function leader, understand their workflow end-to-end, and translate it into the right automation — including knowing when the right answer is to redesign the process first
- A process re-engineering instinct, with the judgment to fix the work before automating it
- A proven track record of driving adoption and behavior change within non-technical teams — not just shipping the tools, but building champions, running training, and sustaining usage until it becomes a habit
- Experience leading a small team and coaching others to build while staying hands-on yourself
- Excellent communication. You can brief the CEO and pair with an engineer on the same day, and those conversations feel equally natural
- Located on the West Coast or Pacific Time Zone
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