[Hiring] Director, AI Enablement @Patriot Growth Insurance Services and Partner Agencies

Role Description

We are seeking a strategic and execution-oriented Director of AI Enablement to lead the practical adoption of AI capabilities across Patriot Growth Insurance Services. This role partners closely with business and technology leaders to identify high-impact AI opportunities, establish governance and adoption standards, and scale AI-enabled workflows that improve productivity, service delivery, and operational effectiveness. The ideal candidate combines strong business acumen with technical fluency and is capable of translating emerging AI capabilities into measurable business outcomes across a complex, fast-growing organization. This position plays a critical role in building Patriot’s long-term AI operating model and enterprise enablement strategy.

Work Arrangement

This is a full-time, fully remote position.

Professional Responsibilities

• Develop and maintain Patriot’s enterprise AI enablement roadmap in partnership with the CIO, IT leadership, and business stakeholders across the organization.
• Identify, prioritize, and govern AI initiatives based on business value, operational impact, feasibility, data readiness, and risk considerations.
• Partner with department leaders to evaluate and redesign workflows using AI-enabled solutions, including automation, knowledge retrieval, decision support, and workflow assistance.
• Establish and manage enterprise AI governance standards, including acceptable-use policies, risk management frameworks, vendor evaluation processes, and human oversight requirements.
• Collaborate with Security, Legal, Compliance, Procurement, and Data teams to ensure AI usage aligns with regulatory obligations, internal standards, and cybersecurity requirements.
• Lead evaluation and implementation efforts related to AI platforms, copilots, workflow automation tools, and Microsoft-centric AI technologies, including Microsoft 365 Copilot and Azure OpenAI capabilities.
• Build scalable AI adoption programs, including employee training materials, usage standards, internal communities of practice, and AI champion networks.
• Partner with Architecture and Data teams to improve data quality, knowledge management, taxonomy, and content readiness to support effective AI outcomes.
• Define and track measurable success metrics for AI initiatives, including productivity improvements, workflow efficiency, adoption rates, cost avoidance, and user experience enhancements.
• Oversee the AI enablement portfolio, ensuring projects move from pilot stages into sustainable, enterprise-supported operating models.
• Collaborate with vendors, implementation partners, and internal stakeholders to evaluate technology solutions while minimizing unnecessary complexity and operational risk.
• Prepare executive-level reporting, business cases, and roadmap updates for senior leadership and key stakeholders.

Qualifications

• Bachelor’s degree in Information Technology, Computer Science, Business, Engineering, Data Analytics, or a related field, or equivalent professional experience.
• 8+ years of experience in technology, digital transformation, enterprise systems, automation, AI enablement, data, or related functions.
• Demonstrated experience leading cross-functional technology or transformation initiatives from strategy through 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 partnering with business stakeholders to identify operational pain points and implement technology-enabled process improvements.
• Familiarity with AI governance, data privacy, cybersecurity, vendor risk management, and responsible AI frameworks.
• Experience evaluating enterprise SaaS platforms, implementation partners, and AI technology vendors.
• Strong communication and presentation skills, with the ability to translate 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.
• Proven ability to operate effectively across technical and non-technical teams while influencing without direct authority.
• Strong organizational, analytical, and problem-solving skills with the ability to manage multiple priorities in a fast-paced environment.

Benefits

• Medical, Dental, and Vision Benefits
• Flexible Spending Account (FSA) and Health Savings Account (HSA) and Commuter Transit Programs
• 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

Pay Range

$180,000 - $195,000 per year depending on experience.

*A wide salary range is posted for this position and any job offer is based upon a salary analysis to comply with the required state pay transparency law. The salary analysis considers relevant experience, education, certifications, and seniority as compared to others doing substantially similar work. There is no guarantee an offer will be at the top of the posted range based on the salary analysis.

Company Description

Patriot Growth Insurance Services is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, citizenship or immigration status, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, leave of absence, compensation, benefits, and training. Patriot makes hiring decisions based solely on qualifications, merit, and business needs at the time. For more information, read through our EEO and DE&I Policy located on our website at www.patriotgis.com.