The Talent Problem in Insurance Just Got a Lot More Complicated

I've had the same conversation with insurance technology and HR executives at least a dozen times this year. The pattern is impossible to ignore: technology strategies are accelerating, but the talent needed to execute them isn’t keeping pace.

Carriers are investing aggressively in cloud, data platforms, and digital transformation. AI has only intensified the urgency. Yet here’s what’s often left unsaid: most insurers are still running on systems that are 20, 30, or even 40 years old. Policy admin platforms that predate the internet. Monolithic claims systems. Mainframes. Data scattered across dozens of silos.

That legacy footprint makes the leap to AI far harder than it looks from the outside.

In multiple executive searches this year, the same tension emerges. The vision is clear. The leaders who can actually deliver in these complex, aging environments?  Very hard to find.

AI Has Rewritten the Skill Requirements Almost Overnight

A few years ago, transformation was difficult but familiar: migrate to the cloud, stabilize infrastructure, modernize data, improve security, and build DevOps capability. Then AI arrived—and suddenly the rules changed.

AI doesn’t just need data. It needs clean, connected, high-quality data.
Legacy systems weren’t designed to provide that. So now insurers need leaders who can:

• Modernize core platforms without disrupting business operations
• Build AI-ready data architectures on top of decades of technical debt
• Automate workflows never designed for automation
• Balance rapid innovation with regulatory compliance
• Sequence modernization work in the right order

Leaders who understand both AI and legacy execution dynamics? That’s one of the rarest profiles in the industry—which is why more carriers are looking beyond insurance for answers.

The Best AI Talent is Coming From Unexpected Places

In recent searches, the strongest candidates didn’t “grow up” in insurance. They came from industries that already solved the challenges insurers are just now confronting:

• Fintech leaders who built ML models on decades-old banking infrastructure
• Retail and logistics executives who implemented AI across legacy ERP systems
• Healthcare innovators who balanced sensitive data, strict regulation, and outdated EMRs
• SaaS builders who created scalable data foundations across hybrid clouds

Their differentiator wasn’t domain expertise—it was proof of modernization and AI execution in complex, regulated environments.

And that’s exactly what insurers need now.

The New Playbook: Blended Talent Models

Insurers making real headway in AI aren’t trying to do everything internally. They’re adopting blended models that combine deep institutional knowledge with specialized external expertise:

• Internal leaders who own strategy and architecture
• Strategic partners who accelerate modernization and delivery
• Specialists in AI, data engineering, and cloud who fill immediate gaps
• Product leaders who translate AI into customer and operational outcomes

This isn’t outsourcing—it’s orchestration. It’s how to move fast in a legacy-bound environment without breaking things.

What CIOs, CTOs, and CHROs Should Do

1. Redefine “relevant experience.” Stop asking, “Do they know insurance?” Start asking, “Have they modernized legacy systems and delivered AI in complex, regulated contexts?”
2. Align talent and modernization roadmaps. If you’re planning system upgrades, data cleanup, or AI pilots, your talent strategy needs to run in parallel—not trail behind. 
3. Build a strategic partner ecosystem. AI evolves quickly. Legacy systems don’t. Partners help bridge that gap while internal teams build sustainable capability.

The Bottom Line

AI isn’t the true disruptor here—talent is.

The carriers that win in the next few years will be those that treat talent strategy as a modernization lever, combining internal strength, external expertise, and leaders who can modernize and innovate at the same time.

PGP + Ippon Partnership

Ippon Technologies and Purple Gold Partners (PGP) have formed a strategic partnership to help banks and insurers accelerate complex transformation by uniting leadership, talent, and technology. By combining PGP’s expertise in sourcing and advising executive, product, and technology leaders with Ippon’s deep capabilities in digital modernization, cloud, data, and AI, the partnership delivers end-to-end solutions that align C‑suite vision with scalable engineering execution. Together, Ippon and PGP help financial institutions break through transformation roadblocks, strengthen regulatory and risk postures, and turn technology investments into measurable business impact.