Director, AI Enablement

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop and sustain the Patriots enterprise AI enablement roadmap in collaboration with the CIO, IT leadership, and business stakeholders throughout the organization.

• Identify, prioritize, and manage AI initiatives based on business value, operational impact, feasibility, data readiness, and risk considerations.

• Collaborate with department leaders to assess and redesign workflows utilizing AI-enabled solutions, which include automation, knowledge retrieval, decision support, and workflow assistance.

• Establish and oversee enterprise AI governance standards, such as acceptable-use policies, risk management frameworks, vendor evaluation processes, and human oversight requirements.

• Work together with Security, Legal, Compliance, Procurement, and Data teams to ensure AI usage complies with regulatory obligations, internal standards, and cybersecurity requirements.

• Lead the evaluation and implementation of AI platforms, copilots, workflow automation tools, and Microsoft-centric AI technologies, including Microsoft 365 Copilot and Azure OpenAI capabilities.

• Create scalable AI adoption programs, incorporating employee training materials, usage standards, internal communities of practice, and AI champion networks.

• Partner with Architecture and Data teams to enhance data quality, knowledge management, taxonomy, and content readiness to support effective AI outcomes.

• Define and monitor measurable success metrics for AI initiatives, including productivity improvements, workflow efficiency, adoption rates, cost avoidance, and enhancements to user experience.

• Oversee the AI enablement portfolio, ensuring that projects transition from pilot stages to sustainable, enterprise-supported operating models.

• Collaborate with vendors, implementation partners, and internal stakeholders to assess technology solutions while minimizing unnecessary complexity and operational risk.

• Prepare executive-level reports, business cases, and roadmap updates for senior leadership and key stakeholders.

⛳️ Requirements

• Bachelor’s degree in Information Technology, Computer Science, Business, Engineering, Data Analytics, or a related field, or equivalent professional experience.

• Over 8 years of experience in technology, digital transformation, enterprise systems, automation, AI enablement, data, or related functions.

• Proven experience in leading cross-functional technology or transformation initiatives from strategy through to implementation and adoption.

• Strong understanding of practical AI use cases, including generative AI, copilots, workflow automation, retrieval-augmented generation (RAG), knowledge management, and AI-assisted decision support.

• Experience collaborating with business stakeholders to pinpoint operational pain points and implement technology-enabled process improvements.

• Familiarity with AI governance, data privacy, cybersecurity, vendor risk management, and responsible AI frameworks.

• Experience in evaluating enterprise SaaS platforms, implementation partners, and AI technology vendors.

• Excellent communication and presentation skills, with the ability to convey technical concepts into clear, business-focused guidance.

• Experience with Microsoft technologies, including Microsoft 365, Copilot, Azure OpenAI, Power Platform, Teams, SharePoint, Purview, and related tools preferred.

• Experience in insurance, financial services, private equity-backed organizations, or other regulated industries preferred.

• Demonstrated ability to operate effectively across both technical and non-technical teams while influencing without direct authority.

• Strong organizational, analytical, and problem-solving skills with the capability to manage multiple priorities in a fast-paced environment.

🏝️ Benefits

• Medical, Dental, and Vision Benefits

• Flexible Spending Account (FSA) and Health Savings Account (HSA)

• Company paid Short-Term Disability, Long-Term Disability, and Group Term Life

• Company paid Employee Assistance Program

• Paid Parental Leave

• Paid holidays

• Personalized PTO

• 401(k) with employer match