Client Principal - AI Consulting (Property & Casualty Insurance)

CloudFactory
Chicago, IL

At CloudFactory, we are a mission-driven team passionate about unlocking the potential of AI to transform the world. By combining advanced technology with a global network of talented people, we make unusable data usable, driving real-world impact at scale.

More than just a workplace, we’re a global community founded on strong relationships and the belief that meaningful work transforms lives. Our commitment to earning, learning, and serving fuels everything we do as we strive to connect one million people to meaningful work and build leaders worth following.

Our Culture

At CloudFactory, we believe in building a workplace where everyone feels empowered, valued, and inspired to bring their authentic selves to work. We are:

  • Mission-Driven: We focus on creating economic and social impact.
  • People-Centric: We care deeply about our team’s growth, well-being, and sense of belonging.
  • Innovative: We embrace change and find better ways to do things together.
  • Globally Connected: We foster collaboration between diverse cultures and perspectives.

If you’re passionate about innovation, collaboration, and making a real impact, we’d love to have you on board!

About the Role

Property & Casualty (P&C) insurance is one of the most AI-active, and most complex sectors in financial services.

While the opportunity is significant, most insurers struggle to move from promising pilots to production-grade AI. Challenges around data quality, model explainability, human-in-the-loop requirements, and regulatory scrutiny continue to slow progress.

CloudFactory is built to solve exactly this.

As Client Principal, AI Consulting (Property & Casualty Insurance), you will be the senior commercial and strategic leader for our P&C sector. You will operate as a trusted advisor to executive stakeholders across large carriers, specialty insurers, and insurtechs, shaping AI transformation agendas and leading engagements from origination through delivery oversight.

This is a high-impact, externally facing role for someone who can open doors, lead complex conversations, and convert opportunity into long-term partnerships.

What You’ll Do

Executive Relationships & Strategic Advisory

  • Build and lead market growth strategy for P&C insurers, reinsurers and insurtechs, to include establishing and owning senior prospect relationships.
  • Engage C-suite and VP stakeholders (Claims, Data, Underwriting, Risk) as a trusted advisor, not a vendor.
  • Operate as a strategic advisor on AI adoption, from use case identification to production deployment and model governance.
  • Lead executive discussions on how AI, particularly human-in-the-loop approaches, can improve efficiency, accuracy, and regulatory defensibility.
  • Align complex stakeholder groups across claims, actuarial, IT, data science, and compliance functions.
  • Identify and drive expansion opportunities within existing accounts.

Business Development & Commercial Leadership

  • Own new logo acquisition, account expansion and P/L management across enterprise P&C clients in the US and Europe.
  • Develop strategic account plans that scale from initial use cases to enterprise-wide AI programs.
  • Own the full commercial lifecycle: discovery, solution framing, proposal development, and executive presentations.
  • Navigate procurement processes, RFPs, vendor risk frameworks, and regulatory constraints effectively.
  • Partner with internal teams to craft tailored, high-impact solutions for insurance clients.

Solution Shaping & Delivery Oversight

  • Identify high-impact AI use cases across the insurance value chain, including:
    • Claims document processing and intelligent document understanding
    • Aerial and satellite imagery analysis for property assessment
    • NLP for policy, coverage, and regulatory interpretation
    • Underwriting data enrichment and risk model validation
    • FNOL automation and subrogation workflows
  • Lead discovery sessions and workshops to uncover transformation opportunities.
  • Translate operational and regulatory challenges into scalable AI solutions.
  • Collaborate closely with data science and engineering teams to ensure successful execution.
  • Maintain accountability for delivery quality, timelines, and client satisfaction.

Thought Leadership & Market Influence

  • Stay at the forefront of AI trends in insurance, including fraud detection, intelligent document processing, and risk modeling.
  • Represent CloudFactory in industry forums, client workshops, and executive discussions.
  • Demonstrate strong awareness of regulatory frameworks (e.g., NAIC guidelines, EU AI Act, model risk management standards).
  • Feed market insights back into product development and go-to-market strategy.

Leadership & Collaboration

  • Lead and influence cross-functional teams across consulting, data science, and delivery.
  • Foster a culture of collaboration, innovation, and continuous improvement.
  • Contribute to knowledge sharing and best practices across engagements.

Requirements

  • Deep P&C Insurance Expertise: Strong understanding of underwriting, claims, risk modeling, and regulatory environments, with insight into key market players and trends.
  • Established Executive Network: Existing VP+ relationships across carriers, specialty insurers, or reinsurers that can be activated immediately.
  • Commercial & Strategic Acumen: Proven ability to translate complex insurance challenges into compelling AI-driven solutions and business value; P/L management experience.
  • Technical Fluency: Solid understanding of AI/ML concepts, including NLP, computer vision, and predictive analytics (no coding required, but strong conceptual grasp is essential).
  • Consulting & Client Leadership: Track record of leading large, complex engagements and influencing senior stakeholders.
  • Executive Presence & Communication: Ability to clearly articulate complex ideas, command executive conversations, and operate as a trusted peer—not a vendor.
  • Leadership Experience: Experience leading cross-functional teams in dynamic, high-stakes environments.
  • Experience: 10+ years in consulting, technology, or AI-driven roles within insurance or financial services.
  • Education: Bachelor’s degree in a relevant field (e.g., engineering, computer science, statistics). Advanced degrees are a plus.

Why This Role

This is not a typical sales or consulting role. It’s an opportunity to sit at the intersection of AI, industry transformation, and commercial leadership, shaping how one of the world’s most complex industries adopts and scales AI.

If you’re someone who thrives in high-impact environments, enjoys operating at executive level, and wants to play a defining role in the future of AI in insurance, we’d love to meet you.

Benefits

  • Compensation: Highly competitive base salary and an aggressive, performance-aligned incentive compensation structure.
  • Comprehensive Benefits: Robust health, dental, vision, and retirement plans.
  • Cutting-Edge Projects: Direct exposure to, and leadership of, advanced AI initiatives with the world's most influential energy corporations.
  • Collaborative Culture: A supportive, high-performance team environment focused on innovation and measurable client success.
  • Professional Growth: Structured access to continuous executive education, mentorship, and accelerated leadership development opportunities.
  • Executive Visibility: Regular interaction with, and direct accountability to, the company’s senior leadership team.

This role represents a unique, high-impact opportunity to define and shape the AI landscape for major global corporations in the energy sector. If you are a highly consultative professional with deep sector knowledge, a passion for AI, and a proven talent for originating and closing complex, strategic enterprise deals, we encourage your application.

Posted 2026-05-14

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