The AI Advantage: From CIO Initiative to C-Suite Priority

The AI era has arrived, but for many, it's stalling at the starting line. While 70% to 95% of AI pilots fail to ever reach production, forward-thinking leaders in the insurance industry are proving that the bridge from "potential" to "payback" is built on strategic alignment and a culture of experimentation.

In Episode 2 of our podcast series, we sat down with three insurance industry leaders who've cracked the code on moving AI from experimental phases to enterprise-wide operations that drive real ROI. Their insights reveal a surprising truth: the barrier to AI success isn't innovation—it's organizational alignment and cultural transformation.

Meet our guests

• Andrew Robinson, CEO and Chairman of Skyward Specialty Insurance, with a background in venture capital and AI-driven insurtech.
• Casey Kempton, President of Personal Lines at Nationwide, overseeing underwriting, claims, and operations for homeowners and auto insurance.
• Keith Schlosser, A multi-time CIO with 35 years of experience in the insurance industry, currently advising AI and private equity firms.

The leadership blueprint: Aligning the C-suite for scale

Getting buy-in across the C-suite and executive level is key. What’s the best approach? “Setting a high bar for financial impact gives leaders permission to challenge the status quo,” says Casey Kempton. “When AI delivers real results, adoption becomes organic rather than mandated … AI and business strategy are no longer separable. Value is created when technology and business leaders own outcomes together, not in handoffs.”

Andrew Robinson agrees. “When people see ideas move from concept to deployment quickly, belief follows. Speed of execution is what aligns leadership—not governance meetings … The most important job of IT is speed—being able to deploy, test, and measure new capabilities continuously. If you slow down, you fall behind.”

Keith Schlosser expanded on those thoughts, noting that communication is often the missing link. “Technology leaders will jump right to the tech when discussing the opportunity. And sometimes they use language that they understand and maybe their colleagues understand, but business leaders … don't necessarily understand it,” he says. “And that puts up unintended roadblocks for progress. As we think about making it a strategic priority [what’s needed] is really a common language, common goals, common vision.”

1. Build an "every employee" AI culture

Success doesn't live in a siloed innovation lab; it thrives when it's part of the organizational fabric.

• Democratize development: Skyward set a goal for every single employee to build a generative AI use case for their specific role to build trust and competence.
• Continuous education: Nationwide’s "Future of Work" program makes data and AI literacy a requirement for continuing education.
• Internal competition: Twice-yearly "tech activation workshops" allow business leaders to showcase successful deployments, creating a "snowball effect" of organic adoption.

2. Solve real problems, not just technical ones

The most compelling business cases aren't always about radical disruption—they are about removing friction.

• The human in the loop: Nationwide uses AI to summarize complex claim files, allowing associates to instantly understand a customer’s history and provide more empathetic, human service.
• Speed to desk: By controlling their own "visual underwriting" desktop (SkyView), Skyward can deploy new AI risk signals to underwriters in days rather than months, bypassing legacy system constraints.

3. Move from chat to act

The future of AI is shifting from conversational interfaces to agentic AI—systems that don't just answer questions but execute complex workflows.

• Precision over proxies: The industry is moving away from proxy data toward actual exposure data (like telematics and real-time payroll) to create hyper-precise pricing.
• Data hygiene is non-negotiable: AI agents are only as effective as the information they can access. Preparing for the next wave requires a relentless focus on cleaning and structuring data.

The path forward for leaders

For CIOs and executive leaders, the message is clear: the technical hurdle is often lower than the cultural one. Moving from pilot to payback requires more than just a successful proof of concept; it demands a fundamental shift in how the entire organization views and interacts with data. By prioritizing literacy, empowering employees at every level, and focusing on high-impact, practical use cases, leaders can bridge the gap between AI potential and measurable business value. In this competitive landscape, the "arms race" isn't just about who has the best tech, but who can integrate it most effectively into the heart of their operations.

"This is an AI arms race... the moment we stop, others are going to catch up." — Andrew Robinson, CEO, Skyward Specialty Insurance

Make sure you listen to the full episode! And tune in in two weeks for episode 3 of the AI Advantage, "Navigating risk, reward, and real-world deployment," where we'll explore how CIOs can mobilize the entire IT organization for AI.