Skip to content
Home » Prompts » How AI is Reshaping Insurance – Insights from a Former CIO

How AI is Reshaping Insurance – Insights from a Former CIO

“Stop the POCs. Start with strategy.” That was the headline quote from my recent conversation with Eshwar Pastapur, a seasoned tech strategist and former insurance CIO who’s now leading Symplyphy.ai. With over 30 years of experience in tech, operations, and insurance, Eshwar offered a no-nonsense view of how AI is transforming the industry—and what leaders must do to avoid falling behind.

From Complexity to Clarity

Eshwar’s superpower, as he puts it, is “turning complexity into clarity.” That mindset has guided him through major transformations—from legacy system overhauls to early chatbot adoption—long before GenAI was a headline.

“Innovation isn’t always about shiny new things,” he said. “Sometimes, it’s about leaving a process better than you found it.”

The AI Imperative: Beyond POCs

Many insurance companies are still stuck in the proof-of-concept (POC) loop. Eshwar was clear: that era is over. “Gone are the days of experimenting. This is the time to start with your strategy. AI should be part of your company’s DNA.”

And he’s not just talking about automation. From underwriting to claims processing, AI is reshaping workflows:

“We’ve reached a point where an AI agent can write and deploy code. That’s not a toy—it’s a strategic capability.”

InsureTechs Are Raising the Bar

Startups like Lemonade and Hippo are creating new expectations around quoting, claims, and service. “They don’t carry the baggage of legacy systems,” Eshwar noted. “They’re resetting customer expectations—and traditional carriers must adapt quickly.”

Small Teams, Big Change

While large carriers may have full R&D teams, mid-sized insurers don’t have that luxury. Yet Eshwar has proven it’s still possible to innovate.

“We didn’t have a dedicated AI team. We carved out time. We made the case. That’s what being a CIO means—finding strategic wins with limited resources.”

Agents and the Human Touch

Even as AI advances, Eshwar believes insurance will remain a relationship business—especially on the commercial side.

“For personal lines, people may prefer a chatbot. But for complex commercial claims? You still need a human who understands the nuance.”

Preparing the Workforce

Eshwar doesn’t predict massive job losses from AI. Instead, he sees a need for re-skilling:

“It’s not about replacement. It’s about enhancement. Underwriters, claims adjusters—they’ll need new tools, but also new training.”

The Rise of the Chief AI Officer

As AI becomes central to enterprise strategy, leadership must evolve.

“The CIO role is shifting. Companies will need Chief AI Officers who can embed intelligence into the core of the business.”

Final Takeaway

AI is no longer optional. Whether you’re running a carrier, managing a team, or building a startup, the time to integrate AI into your strategy is now.

If you’re interested in how to get started, listen to the full conversation on The Innovation Room Podcast https://spoti.fi/4jCHV7Z, or connect with Eshwar on LinkedIn.


Mike Echlin is a co-founder of Veritopa, an AI consultancy helping organizations turn ideas into actionable AI strategy.