Director, AI Enablement

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

About The Role

OpenLoop’s mission is to bring care anywhere by powering telehealth solutions at scale. The Director, AI Enablement is a founding leader responsible for building and scaling the organization’s enterprise AI capability. This role owns the AI platform and delivery of high-impact use cases across the business. Reporting to the VP of Enterprise Technology, this leader operates across strategy and execution—driving roadmap, architecture, and adoption at scale.

What You’ll Do:

• Define and execute the enterprise AI roadmap aligned to business priorities

• Identify, prioritize, and deliver high-impact AI use cases with measurable ROI

• Represent AI strategy in executive and cross-functional forums

• Own the design, deployment, and operation of the enterprise AI platform

• Establish scalable, secure, and compliant AI infrastructure (LLMs, MLOps, integrations)

• Define standards for model lifecycle management (deployment, monitoring, incident response)

• Maintain oversight of AI systems, vendors, and usage across the organization

• Lead end-to-end delivery of AI solutions across clinical, operational, and corporate functions

• Drive adoption and integration into business workflows

• Ensure outcomes are tied to efficiency, cost, or performance improvements

• Partner across IT, Clinical, HR, Operations, and Data teams

• Influence stakeholders and align AI initiatives to enterprise priorities

• Build and scale a multidisciplinary AI team

• Define roles, structure, and ways of working

• Manage budget, tooling, and external resources

• Other duties as assigned

Who You Are:

Required

• 10+ years in technology roles with 4+ years in a leadership or management capacity

• Experience working with scaling enterprise platforms

• Deep understanding of LLM ecosystems, MLOps practices, vector databases, and AI API architectures

• Track record of translating business problems into AI product requirements and delivering solutions

• Strong executive communication skills — able to present complex AI concepts to non-technical audiences

• Experience operating in regulated industries (healthcare, financial services, or similar) preferred but not required

Preferred

• Experience in healthcare IT, clinical decision support, or HIPAA-regulated environments

• Familiarity with AWS AI/ML services (SageMaker, Bedrock, Amazon Connect AI capabilities)

• Experience building teams from the ground up in a new function

• Background in workforce management, BPO technology, or contact center AI

• Advanced degree in Computer Science, Data Science, or related field — or equivalent experience

Our Benefits

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans

• Flexible Spending/Health Savings Accounts

• Flexible PTO

• 401(k) + Company Match

• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.