The Winner & Finalists of the 2023 Ambitious Insurer Awards – North America

After hosting the inaugural Ambitious Insurer Awards at ITI Europe, we couldn’t wait to do the same at ITI in New York. 

In our nomination process, we gathered over 200 global submissions, including 50 for North America. The submissions were fascinating, but ultimately 10 were chosen as finalists, and our panel of judges selected one as the winner.

The Winner: Cowbell’s Cyber Insurance Education

As important as cyber insurance is becoming, 48% of brokers and agents don’t feel comfortable explaining it to their clients. Cyber insurance is a complex and constantly-evolving topic, and the traditional insurance “training” via conferences or webinars just wasn’t keeping up. 

Cowbell Academy offers courses developed by insurance and cybersecurity professionals with extensive agent and broker experience, closing the education gap, helping more customers get the cyber protection they need. 

It’s only been available for a short time, but it’s already exceeded expectations. At the time of the awards, over 23,000 brokers were on the platform. 

We love the way this winner’s story perfectly encapsulates what’s happening across the industry right now: Future-focused visions from the past are becoming reality, the market is latching onto those ideas, and the world is becoming a better place for it.

“When I joined Cowbell, the first thing I said two years ago yesterday, actually, was ‘We really need to take the time to really educate our agents and brokers and policyholders because the cyber insurance industry is very, very new, and a lot of people just aren’t sure exactly how to present it when it comes to selling or even understand why they actually need it.’ … I tried it as a podcast and after five months on air, it became a top 20 Apple podcast for business news… and we turned that into a full-blown e-learning center dedicated to teaching cyber insurance to agents and brokers around the world.” 

-Alexis Cierra Vaughn, AVP of Agency Marketing, Cowbell

Honorable Mentions

Along with Cowbell, the other finalists are doing some truly ambitious and market-changing things.


Migrasure is a venture of Generali to help address the migrant housing crisis by eliminating barriers in the private rental market. Often, landlords see migrants as “high-risk” tenants due to their inability to afford deposits and other liabilities. By leveraging AI and machine learning for tenancy history, cultural mediation, and legal advice, Migrasure plans to instill confidence in landlords and alleviate government expenditure on social housing, with endorsements from many international organizations.

Coterie Insurance

Making the world of business insurance so much easier, Coterie’s new dashboard allows their partners to get bindable quotes in seconds, using only the business name and address. The automated underwriting engine uses AI and machine learning to pull publicly available information to underwrite the risk, making it the fastest and easiest experience for small business insurance out there.


Starting in the construction business, the AXA XL Ecosystem uses modern technology to: 

  • Provide a benchmarking service to evaluate a contractor’s level of technology against their peers and industry trends
  • Curate technology and risk management solutions to improve jobsite performance and safety
  • Bundling policies with technology services to reduce risk

They’re currently expanding beyond construction into property, environmental, casualty, aerospace, specialty niche, inland marine, design professional, and cyber insurance.

Slide Insurance

As an insurtech, Slide launched in Florida in 2022 by veterans to provide a new approach to underwriting for coastal homeowners, a typically highly distressed insurance market.

Policy Expert

Another insurtech, Policy Expert provides proprietary technology and advanced analytics to become the most successful insurance disruptor. (An ambitious undertaking indeed!) In 2022 alone, they: 

  • Saved new customers a total of £42 million compared to what they were paying to other insurers
  • Launched a more accessible “bronze” line of home insurance in response to the cost of living crisis that represents 20% of policies sold
  • Handle over 90% of claims in an automated portal, in as little as 2.4 hours per claim

NEXT Insurance

Of the five million Americans who submitted new small business applications, 30% don’t have insurance coverage, and 90% aren’t sure they have enough. NEXT came up with an embedded insurance solution for pay-as-you-go workers’ compensation that integrates with Gusto payroll technology.


Because 68% of people don’t trust their insurers, and when 80% of chronic disease comes from lifestyle factors, YuLife recognizes that it’s not enough for an insurer to provide help at the point of claim, and that there are shared-value economics in helping people make positive lifestyle changes. Taking hints from the gaming industry, YuLife used behavioral science and game theory to build an app that lets employees access their policies, but also engages them daily. Dubbed by The Atlantic as “a cross between Fortnite and FitBit,” YuLife helps increase average daily step counts by 11%, and 87% claim they feel more energized at work as a result of the app’s help.

Mosaic Insurance

Underwriting for speciality lines has always been more complex and time-consuming than for standard policies. Leveraging their API gateway and advanced AI, Mosaic’s new underwriting portal can provide instant quotes and reduce issuance time from five days to less than two hours, and is expected to support $5 million in new premiums in its first year.


In making access to insurance more democratic, Quility is using technology to provide insurance to American families through various distribution channels, automating the entire lifecycle. Key to their success was an event-driven data warehouse and analytics, digital insurance products, an automation platform, and a robust learning and development system.

What ambition do you have in store for 2023?

After hosting the Ambitious Insurer Awards for the first time this year, we can’t wait to see the kind of cool, ambitious insurance projects that develop in the years to come. We already know ambitious insurers will continue to blow our minds though, because when you have the right underlying technology, anything is possible! 

We also wanted to give a special shout-out and thank you to our amazing panel of judges. Without them, these awards wouldn’t have been possible:

  • William Mak – VP, Strategic Capabilities – New York Life
  • Adam Gladsen – SVP, Head of Cyber Solutions – Swiss Re
  • Ira Sopic – Head of Insurance – Reuters Events
  • Kobi Bendelek – CEO – InsurTech Israel
  • Alex Bond – CEO – FinPro
  • Denise Garth – Chief Strategy Officer – Majesco
  • Lisa Wardlaw – Insurance Digital Strategist – InsurTech Israel
  • Danilo Raponi – Group Head of Innovation – Generali
  • Eugene Shafronsky – Head of Strategy – thinktum
  • Glenn Hofmann – Chief Analytics Officer – New York Life
  • Jeff Shi – Founder – Insurtech Groups
  • Orna Carni – Managing Partner – FinTLV

Stay ahead with the latest insights right in your inbox:

Keep Reading

Share This