Job Description

We're looking for a Director of Artificial Intelligence to lead the organization-wide strategic selection, implementation, and adoption of AI technologies for a tech-enabled insurance brokerage that's modernizing insurance for customers nationwide. This is a rare opportunity to build from the ground up. You will be the architect, evangelist, and operator for AI throughout our growing enterprise—driving impact from back-office automation to client-facing innovation.

This isn’t a theoretical R&D role. You’ll be at the center of business transformation, helping our people do more with less, augmenting decision-making, and helping us deliver exceptional service at scale. You’ll work closely with executive leadership, IT, operations, marketing, and every other function to ensure that AI is thoughtfully but aggressively integrated into the DNA of the company.

About The Company

They're building the future of insurance—one smart acquisition at a time. As a dynamic insurance agency roll-up, they're uniting best-in-class firms under a single vision: to operate faster, leaner, and more intelligently than legacy incumbents. A core pillar of that vision? Artificial Intelligence. They're not just experimenting—they're embedding AI across every layer of our business to transform how we operate, serve clients, and scale.

Compensation, Benefits, Location:

• 100% employer-paid healthcare for you and your dependents
• Base salary DOE $200,000-$250,000 annually + substantial performance-based bonus opportunity + Equity/Profit Participation
• Two weeks PTO annually, one week paid sick annually, 14 days paid federal holidays
• Schedule flexibility
• Opportunity to relocate to Miami
• Beautiful, central office location in Brickell area of Miami

Responsibilities

Strategic Leadership

• Define and lead the company’s AI strategy in alignment with business goals.
• Evaluate and select best-fit AI platforms, tools, and vendors (initial stack includes OpenAI + Azure).
• Drive the ethical, compliant, and responsible use of AI technologies.

Implementation & Integration

• Design and execute AI implementation roadmaps across departments: sales, underwriting, claims, marketing, HR, finance, etc.
• Integrate AI into our Agency Management System (AMS), CRM, communication tools, and back-office workflows.
• Own proof-of-concepts, pilots, and scaling of successful AI initiatives.

Enablement & Adoption

• Partner with functional leaders to identify use cases and train staff on AI tools and capabilities.
• Build internal enablement programs to promote AI literacy and confidence across all levels of the company.
• Serve as an internal consultant to ensure AI is used productively and responsibly in day-to-day operations.

Technical Oversight

• Collaborate with engineering and data teams (internal or external) to operationalize AI models and services.
• Stay current on emerging AI technologies, especially around LLMs, RPA, NLP, and predictive analytics.
• Monitor AI system performance, efficacy, and ROI across the organization.

Qualifications

Must-Have

• 5+ years of experience in AI/ML, data science, or intelligent automation, with a track record of delivering real business impact.
• Proven experience implementing AI in operational workflows, ideally in a multi-entity, B2C or B2B2C environment.
• Deep knowledge of LLMs, RAG systems, Azure AI stack, OpenAI API, and general AI platform management.
• Strong project management and change management skills.
• Excellent communication skills, with the ability to translate complex AI concepts into practical applications for non-technical users.

Bonus Points

• Experience in the insurance industry or highly regulated environments.
• Familiarity with Agency Management Systems (AMS) and insurance-specific CRMs.
• Exposure to process automation tools like Power Automate, UiPath, Zapier, etc.
• Passion for building internal tools, bots, and workflows that "just make things work better."

Why Join?

• Impact: You won’t just be a leader — you’ll be an enterprise-wide catalyst for change.
• Ownership: Competitive compensation package with significant upside potential, including equity/profit participation.
• Autonomy: Full support from leadership to build a world-class AI-first operating environment.
• Innovation Playground: We’re not afraid of bold ideas. We want to push the envelope (responsibly).

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