Senior Director, AI Enablement & Operations - Enterprise AI

OneOncology is positioning community oncologists to drive the future of medical care through a patient-centric, physician-driven, and technology-powered model to help improve the lives of everyone living with cancer and other diseases. Our team is bringing together leaders to the market place to help drive OneOncology’s mission and vision.

Why join us? This is an exciting time to join OneOncology. Our values-driven culture reflects our startup enthusiasm supported by industry leaders in oncology, urology, technology, and finance. We are looking for talented and highly-motivated individuals who demonstrate a natural desire to improve and build new processes that support the meaningful work of independent physicians and the patients they serve.

Job Description:

Reporting to the Chief Technology Officer, the Senior Director, AI Enablement & Operations is responsible for leading OneOncology’s enterprise approach to AI governance, validation, operational oversight, and adoption. This role establishes and manages the frameworks necessary to ensure AI solutions are evaluated according to their level of risk, appropriately validated before deployment, continuously monitored in production, and supported by clear controls and audit-ready documentation. The Senior Director will lead a small, growing team responsible for AI enablement, validation, and operations, establishing clear priorities, accountability, and development plans as the function scales. 

The Senior Director will initially lead the enterprise validation and operational oversight of Risa, OneOncology’s autonomous prior authorization agent, and will expand these standards across the broader AI portfolio. The role partners closely with Technology, Security, Compliance, Clinical, and business leaders to enable the responsible adoption of AI across the organization, balancing speed and innovation for lower-risk use cases with rigorous oversight for AI solutions that may impact patient care, protected health information, or other high-risk workflows. 

Responsibilities: 

• Own and operationalize the enterprise AI validation framework, risk-tiered by patient-safety impact and PHI exposure: low-risk productivity AI moves quickly under standard security review; AI that affects patient care or moves PHI carries the full validation plan. 

• Require pre-production accuracy testing against defined performance thresholds before any high-risk AI system enters production use. 

• Stand up continuous production monitoring - model drift, error rates, throughput and backlog, and change detection - with defined alerting thresholds and escalation paths. 

• Define and enforce human-in-the-loop boundaries for agentic workflows, including any automation that transmits PHI to external parties such as payor portals. 

• Maintain rollback provisions for every high-risk AI system and ensure they are tested and executable. 

• Retain validation and monitoring evidence in existing enterprise systems (SIEM/Azure, ServiceNow, SharePoint, OneAnalytics/Databricks) in a form that satisfies SOX ITGC expectations and parent-company audit readiness. 

• Lead end-to-end validation of our prior authorization agent, including its agentic workflows that move PHI into external payor portals. 

• Establish the accountability model for agent oversight functions - audit trail, explainability, drift detection, error monitoring, and performance benchmarking. 

• Operate a single enterprise intake for AI pilot requests; no AI pilot proceeds without success criteria and kill criteria defined at intake. 

• Run structured vendor evaluations or RFPs by product category - one selection process per category rather than concurrent overlapping pilots. 

• Conduct vendor diligence covering security posture, PHI handling, data rights, integration burden, and independent testing of model performance claims. 

• Own production operations for AI systems: incident response, change control, and coordination with security, integration, and platform teams. 

• Enable rapid, safe adoption of low-risk productivity AI (drafting, document review, summarization) across the enterprise with clear usage guidance. 

• Operate in a hub-and-spoke partnership model with business units - compliance, change control, and security architecture remain enterprise functions; delivery is shared. 

• Report AI portfolio status, risk posture, and validation progress to executive leadership on a defined cadence. 

• Own the Claude Enterprise platform end to end: administration, security configuration, usage policy, and the enterprise adoption roadmap. 

• Drive adoption through a forward-deployed methodology - embed with business teams (RCM, clinical operations, finance, practice operations) to build agents, skills, and workflows inside real work, so adoption is earned in context rather than mandated from the center. 

• Own the enterprise connector strategy: integrating Claude with Salesforce, Monday.com, ServiceNow, Databricks, GitHub, Microsoft 365, and Workday through MCP under enterprise security architecture. 

• Build and curate the enterprise library of skills, agents, and prompt patterns; run enablement programs and a champions network to scale what works. 

• Measure and report value realization - active usage, workflows in production, and time returned to clinical and business teams. 

• Lead and develop a small team responsible for AI enablement, validation, and operational oversight, providing clear direction, coaching, performance management, and prioritization. 

• Build the AI enablement function over time, assessing organizational needs, defining roles and responsibilities, and evolving the team structure and capabilities as OneOncology’s AI portfolio grows. 

• Additional responsibilities as assigned to help drive our mission of improving the lives of everyone living with cancer. 

Qualifications: 

Required 

• 10+ years of progressive technology leadership, including 3+ years in AI/ML delivery, model validation, MLOps, or clinical/regulated systems validation. 

• Healthcare experience with working command of HIPAA and PHI handling obligations; familiarity with revenue cycle or clinical workflows strongly preferred. 

• Demonstrated experience building governance, validation, or quality-assurance programs for production systems - including monitoring, change control, and audit evidence. 

• Working knowledge of SOX IT general controls and experience supporting internal or external audit. 

• Demonstrated people leadership experience, including managing and developing technical or cross-functional teams and building team capabilities as organizational needs evolve. 

Preferred 

• Familiarity with AI risk frameworks (e.g., NIST AI RMF) and with agentic/LLM-based systems in production. 

• Experience in oncology, specialty care, or multi-practice healthcare platforms. 

• Experience with the relevant platform stack: Azure, Databricks, ServiceNow, and healthcare integration (HL7/FHIR). 

Essential Competencies: 

• Executive communication skills, with the ability to translate complex AI/model risk into clear business and financial terms for C-suite and board audiences. 

• Strong judgment and risk management skills, particularly in evaluating AI-related operational, compliance, and patient-safety risks. 

• Ability to lead cross-functional governance and decision-making across technology, security, compliance, clinical, and business stakeholders. 

• Ability to operate effectively in a complex, regulated environment, balancing innovation and speed with appropriate controls and oversight. 

• Attendance is an essential job function.