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Director of AI

Piper Companies, WorkFromHome, MD, United States


Piper Companies is looking for a Director of AI to join a thriving insurance company. This is a hybrid position and requires the candidate to be onsite 3 days a week.

Essential Duties of the Director of AI :

  • Define and execute the enterprise AI strategy aligned to business objectives and digital transformation priorities
  • Evaluate and integrate leading AI capabilities from Microsoft, OpenAI, Anthropic, and Google to ensure the organization leverages best-in-class innovation
  • Lead evaluation and decision‑making for build vs. buy AI solutions, balancing speed‑to‑market, total cost of ownership, scalability, security, and strategic differentiation
  • Lead the design, development, and deployment of AI and generative AI solutions using Azure AI Services, Azure OpenAI, and other approved AI platforms
  • Define and track KPIs to measure AI value realization
  • Establish best practices for experimentation, architecture design, vendor evaluation, and AI solution engineering

Qualifications of the Director of AI :

  • Bachelor's degree preferred but not required
  • 15+ years experience leading technology, software development, and process improvements
  • 5+ years working with Microsoft cloud technologies and within the Azure ecosystem
  • 3+ years working and implementing AI solutions
  • Experience leading teams through digital transformation and scaling AI capabilities
  • Experience with Lifepro/Btrieve desirable

Compensation for the Director of AI :

  • $200,000 - $240,000 (based on experience)
  • Comprehensive benefit package; Cigna Medical, Cigna Dental, Vision, 401k w/ ADP, PTO, paid holidays, sick Leave as required by law

This job opens for applications on 3/23/26. Applications for this job will be accepted for at least 30 days from the posting date

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