Director, AI Enablement (Remote)

About Patriot Growth Insurance Services: Founded in 2019, Patriot is a growth-focused national insurance services firm that partners with employee benefits and property and casualty agencies across the United States. Patriot is currently ranked as the 25th largest broker in the U.S. by Business Insurance and has been named to the 2025 Inc. 5000 list of fastest-growing companies. With over 2,100 employees operating in 150+ locations in over 45 states, Patriot’s collaborative model delivers resources and strategic support to its agencies. Patriot creates true alignment with its partner agencies, and its operating philosophy fosters enhanced career opportunities for its dedicated and professional team. We are committed to working with like-minded individuals who share our vision of creating an insurance agency focused on operational excellence and a relentless pursuit of growth.

Position Overview: 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, enterprise enablement strategy, and responsible AI adoption framework.

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.
• Establish and maintain an enterprise AI intake, prioritization, and governance model to evaluate, approve, monitor, and scale AI initiatives across business functions.
• Identify, prioritize, and govern AI initiatives based on business value, operational impact, feasibility, data readiness, risk considerations, and change management complexity.
• Partner with department leaders to evaluate and redesign workflows using AI-enabled solutions, including automation, knowledge retrieval, decision support, workflow assistance, and operational efficiency improvements.
• Build and lead an internal AI champion network to encourage adoption, gather feedback, share best practices, and support scalable enablement efforts across departments.
• Classify, evaluate, and mature field-built or locally developed AI solutions by partnering with business teams to assess business value, technical feasibility, operational impact, and enterprise applicability.
• Review locally developed AI solutions and determine whether solutions should be scaled, rebuilt, integrated into enterprise systems, retired, or maintained as local productivity tools based on business needs, governance standards, and long-term supportability.
• Establish and maintain enterprise AI governance standards, including acceptable-use policies, risk management frameworks, vendor evaluation processes, human oversight requirements, and responsible AI practices.
• Collaborate with Security, Legal, Compliance, Procurement, Data, and IT teams to ensure AI usage aligns with regulatory obligations, internal policies, cybersecurity standards, privacy requirements, and risk mitigation expectations.
• Lead evaluation and implementation efforts related to AI platforms, copilots, workflow automation tools, knowledge retrieval systems, and Microsoft-centric AI technologies, including Microsoft 365 Copilot, Azure OpenAI, Power Platform, Teams, SharePoint, and related tools.
• Evaluate vendor solutions, internal tools, and technical implementations with strong technical judgment, challenging vendors and solution builders to ensure practical, scalable, secure, and supportable outcomes.
• Assess technical architecture, integrations, production readiness, scalability, maintainability, and long-term support requirements for AI-enabled solutions and platforms.
• Distinguish high-value, business-relevant AI opportunities from low-value experimentation, vendor hype, or “AI theater” by focusing on measurable operational and business outcomes.
• Build scalable AI adoption and enablement programs, including employee training materials, usage standards, communities of practice, AI champion networks, and structured feedback mechanisms.
• Partner with Architecture and Data teams to improve data quality, taxonomy, knowledge management, content readiness, and governance frameworks that support effective AI outcomes.
• Define, monitor, and report measurable enterprise success metrics for AI initiatives, including productivity gains, workflow efficiency, adoption rates, cost avoidance, service improvements, employee experience enhancements, and realized business value.
• Create executive-level reporting frameworks that clearly communicate where AI is creating measurable enterprise value, where adoption is accelerating, and where investments are underperforming or require adjustment.
• Oversee the AI enablement portfolio, ensuring initiatives move from pilot stages into sustainable, enterprise-supported workflows and operating models.
• Collaborate with vendors, implementation partners, and internal stakeholders to evaluate AI solutions while minimizing unnecessary complexity, operational risk, shelfware, and low-value technology investments.
• Prepare executive-level reporting, business cases, implementation roadmaps, and program updates for senior leadership and key stakeholders.
• Stay informed on emerging AI technologies, enterprise use cases, governance trends, and industry best practices to support continuous improvement and long-term enablement success.

Qualifications and Requirements:

• 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, business transformation, or enterprise enablement 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, AI-assisted decision support, and business process enablement.
• Demonstrated technical fluency with the ability to challenge vendors, evaluate solution architecture and integrations, assess production readiness, and determine long-term scalability and supportability of AI solutions.
• Experience partnering with business stakeholders to identify operational pain points, redesign workflows, and implement technology-enabled process improvements.
• Familiarity with AI governance, responsible AI frameworks, data privacy, cybersecurity, vendor risk management, and enterprise compliance considerations.
• Experience evaluating enterprise SaaS platforms, AI technologies, implementation partners, and technology vendors.
• Strong communication and presentation skills, with the ability to translate technical concepts into practical, business-focused guidance for technical and non-technical audiences.
• 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 distinguish meaningful AI value from low-impact experimentation or “AI theater” while aligning investments to measurable business outcomes.
• Proven ability to influence across technical and business teams without direct authority while driving adoption and organizational alignment.
• Strong organizational, analytical, and problem-solving skills with the ability to manage multiple priorities in a fast-paced environment.

Why Patriot Growth Insurance Services: We offer the opportunity to be a part of one of the fastest-growing insurance companies since its inception. We strive to create a flexible and collaborative environment for our employees, and our goal is to provide enhanced career opportunities for our dedicated and professional team. In addition to a competitive salary, we provide a comprehensive health and welfare program to employees, family members and domestic partners. Employees are eligible for benefits coverage the first of the month following 30 days of employment. We offer:

• 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.

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.