How Jonathan Cooper Is Building a Smarter Insurtech for Travel—and Why He Started at 43

In a world where most startup founders are under 35, Jonathan Cooper decided to launch an Insurtech firm at the age of 43.

What makes his journey even more compelling?

He didn’t just start a company—he’s reshaping how travel insurance works for the digital age.

In this episode of FS Brew, we explore the origin story, operating model, and mindset behind WIS Group, Jonathan’s fast-growing insurance platform.

From IBM to Insurance—By Accident

Jonathan didn’t plan on getting into insurance.

Back in 1985, he left school at 16 and took a job at IBM. It was the pre-Microsoft era, and IBM was still the behemoth of tech.

But the size and ambiguity of the company left him restless.

“I couldn’t figure out what I was doing at IBM. It just didn’t click.”

Then he saw a newspaper ad for a claims handler role at a local insurer.

It was a spontaneous move, but it led to a 40-year career in insurance—ranging from frontline claims to running large teams and managing national portfolios.

Why Start WIS Group at 43?

Jonathan had a solid corporate career.

So why leave it behind?

“I wanted to build something nimble. Something that solved real problems, not just optimized legacy processes.”

At 43, he co-founded WIS Group—Worldwide Insurance Solutions, a platform focused on:

• Travel insurance

• Cyber coverage

• Pet and gadget insurance

Unlike traditional insurers, WIS does not sell directly to customers. It operates in a B2B2C model, distributing policies through:

• Airlines

• Travel portals

• Brokers

• Online platforms

This embedded distribution model isn’t just more scalable—it’s more aligned with consumer behavior.

WIS Group’s Product Philosophy: Keep It Simple

One of the reasons WIS Group has gained traction is its focus on simplicity.

Jonathan breaks it down:

“The biggest friction in insurance is complexity. We’ve simplified the buying process, reduced jargon, and focused on real-time integrations.”

Here’s how that shows up in their offerings:

Their vision is to distribute insurance where the customer already is, rather than asking people to seek out policies proactively.

The Travel Industry’s Hidden Revenue Opportunity

Jonathan believes travel insurance is vastly underutilized as a revenue driver for travel platforms.

“Most OTAs and airlines see insurance as a checkbox. But if it’s personalized and timely, it becomes a serious ancillary income stream.”

Key changes he sees in the sector:

• Personalization through AI: Travelers now expect tailored coverage. AI allows for real-time product customization based on trip duration, destination, age, and even local health risks.

• Embedded design: Travel insurance shouldn’t be a pop-up or redirect. It should be part of the checkout flow.

• Ancillary revenue mindset: Airlines and OTAs are realizing that insurance isn’t just protection—it’s profit.

WIS enables this with plug-and-play APIs and fast underwriting logic.

Embedded Insurance: Buzzword or Real Value?

There’s a lot of hype around embedded insurance.

Jonathan’s take?

“It’s real. But only when the product is relevant, timely, and seamless.”

Here’s what matters:

• Relevance: Offering gadget insurance when someone buys a phone—not three days later.

• Timeliness: Matching insurance options to the purchase moment.

• Seamlessness: No extra logins, forms, or jargon.

WIS uses a modular architecture that supports real-time quoting, straight-through processing, and customer support via API.

Local Market Advantage: Building in the UAE

WIS Group is proudly built in the UAE, and Jonathan believes this has been a key asset.

“Being local gives us insight. We understand regulators, distribution quirks, and cultural buying patterns.”

Examples include:

• Localized compliance for DIFC and mainland distribution

• Building bilingual product flows (Arabic + English)

• Working with local reinsurers and travel aggregators

The UAE’s fintech-friendly regulators and multicultural consumer base make it a prime sandbox for innovation.

Future Growth: Saudi Arabia and Europe on the Radar

When asked about next steps, Jonathan doesn’t hesitate.

“We’re already eyeing Saudi Arabia. The potential is huge, especially with Vision 2030 and travel sector growth.”

Europe is next, but it’s more complex.

• Licensing is fragmented

• Regulatory approvals take longer

• Consumer expectations vary widely

Still, Jonathan is confident. His strategy: enter through niche partnerships, stay API-first, and localize fast.

Life Lessons: Reinvention at 40+

One of the most striking parts of the episode is Jonathan’s personal journey.

He’s lost over 40 kilograms, picked up new hobbies, and rebooted his mindset—all while building a high-growth company.

“Entrepreneurship forced me to rethink everything—my health, habits, how I spend my time.”

His advice to mid-career professionals:

• It’s not too late to build.

• Start with something small but meaningful.

• Solve one real problem, not ten hypothetical ones.

Key Takeaways from the Episode

🎯 Embedded wins when it’s invisible, timely, and relevant.

💡 Personalization is the unlock for monetizing travel insurance.

🌍 UAE is a strategic launchpad for Insurtech across MENA.

🔥 You can start your founder journey at any age.

⚙️ Simplicity and API-first design are competitive advantages.

Why This Matters

Insurance has long been overdue for disruption. And yet, most Insurtechs still struggle with customer trust, retention, and integration challenges.

WIS Group is solving these problems from the distribution side rather than the underwriting side.

They don’t want to be the insurer of record. They want to own the experience layer, where product meets consumer.

That’s where trust—and margins—live.

Final Word from Jonathan

“Insurance is the product nobody wakes up wanting to buy. But if you meet the customer at the right time, with the right message, it becomes a no-brainer.”

Listen to the Full Episode

🎧 Available on Spotify, Apple Podcasts 

📺 Watch on YouTube