Insurtech is still a relatively young sector defining assumptions. Despite some light quarters for insurtech investment in late 2017 and early 2018, the segment roared back with back-to-back billion-dollar quarters of worldwide investment. This included some of the largest rounds ever, with rounds in the hundreds of millions for companies ranging from turnkey usage-based insurance provider Cambridge Mobile Telematics (from last year’s list) to health insurance disruptor Oscar (which appears on this year’s edition).

There’s a key reason for this: Insurers are getting more comfortable working with insurtechs as thesector has evolved and matured. Successful use cases across technologies like artificial intelligence, computer vision and even blockchain have popped up. The trepidation has largely worn off and insurers see insurtechs as their partners in transformation, not enemies to be feared. And insurance experts are finding their voice in being able to communicate a new vision for their industry.

In order to assemble the list on the following pages, Digital Insurance editors consult third party experts, including some who have previously been on the list, to identify the players representing the top level of the game as it stands this year. Their work will shape the conversation around insurance innovation and influence future editions.

Nicquana Howard, Peggy Bresnick, Anne Gabriel and Sharon Goldman contributed reporting.
Guy Russ, Church Mutual
Guy Russ
Russ is responsible for the CM Sensor program, which encompasses how Church Mutual selects, distributes, and leverages data from sensors that are installed in its insured properties. A recent expansion of the program uses Wi-Fi to transmit data rather than cellular networks, which Russ explains will allow smaller churches to participate in the program. He adds that the impact of the sensor program has been transformative on the organization -- Church Mutual is hiring and training more data scientist internally. And, the ROI has been solid: at a cost of $3 million to the insurer, Russ estimates about $10 million has been saved on vlaims costs.
Tracey Berg, Cerity
Former insurance-carrier CIO Berg launched Cerity, an insurtech startup focused on providing easy-to-access workers’ compensation coverage for small businesses, in January 2019. Spun out of Employers Holdings — the last place Berg served as a CIO — the new company is allowing her to leverage her experience as a carrier-side technology leader while exploring the breadth of what insurtech has to offer. Cerity relocated to the Austin area this year to take advantage of the wealth of technology talent in the area. Berg will draw on her long career in insurance tech — she started at Assurant before working as West Bend Mutual’s CIO for nearly a decade — as she stewards this new company.
Rashmi Melgiri and Inaki Berenguer, Coverwallet
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The New York-based insurtech Coverwallet has been working to improve the insurance-buying experience for small business owners, while preserving the value of the insurance agents and brokers who traditionally have served this sector. The company has been working especially closely with The Hanover, which was the first client for its CoverWallet B2B platform in 2018 and used the startup’s tech for its new Insurago platform for agents. The company has also attracted international attention with clients in Spain and Switzerland. In late 2018, Coverwallet added a second, 100-person office in Victor, N.Y., just outside Rochester.
Mark Frederick (pictured) and Gabriel Glynn, Makusafe
Another beneficiary of the Des Moines insurtech cluster is Frederick and Glynn’s Makusafe, which is producing wearable technology and accompanying data and analytics software to quantify jobsite safety and accompanying risk for commercial insurers. The locally based company graduated from the Global Insurance Accelerator in 2018 and raised a $3 million seed round. Its technology is being piloted by insurers including AF Group, which is planning to launch a pilot this year, according to VP and head of underwriting Abel Travis, a 2018 Innovator to Watch. “The data that we’re putting in front of [clients] should drive a change in behavior,” Travis says.
Michael Klein, Travelers
While some insurance companies and executives have been wary of Amazon -- whose overtures to insurance have increased over the past year -- Klein and Travelers have entered a partnership with the online retailer to provide discounts on Amazon’s suite of smarthome devices, with the goal of reducing risk in their customers’ homes. “We want to be where our customers are. Establishing a Travelers storefront on Amazon makes it easier for our customers to access discounted smart home technology that can help protect their property. We simply see it as a way to extend our advantage in risk expertise and provide great experiences for our customers, agents and brokers,” he says.
Mario Schlosser, Oscar
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The health insurance startup Oscar has weathered perhaps its biggest challenge ever: The uncertainty over the Affordable Care Act from the early Trump administration. Now, the company is focused on growth, using digital technology to improve as much of the health insurance and care delivery system as it can. Most recently, it signed on with wearable device analytics company Cardiogram to cover the latter’s heart-monitoring capabilities. Investors believe in the company too: It raised a whopping $375 million from Google parent Alphabet in late 2018.
Mike Fields, State Farm
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Blockchain hasn’t been adopted especially rapidly in insurance, but every new pilot improves the industry’s comfort with the technology, which emerged from the crypto-currency boom and promises a decentralized, secure ledger of transactions. Fields’ team at State Farm -- the largest P&C insurer by market share in the U.S. -- developed and rolled out a blockchain capability for subrogation in late 2018. But most intriguingly, the carrier’s innovation unit, Red Labs, has brainstormed “about 50” use cases for the technology, with a handful of them in progress, Fields says. “We have to understand what it means to get things going and work with competitors in the right way on blockchain initiatives,” he says, potentially showing a way forward for wider deployments.
Jason Andrew, Limelight
Andrew’s Limelight Health, which provides API-based software to automate and digitalize the group benefits space, is on an upward trajectory. The company raised more than $35 million last year in a funding round that included investment from several insurance carrier venture arms. These included The Principal, which recently inked an agreement to integrate Limelight’s quoting, rating and renewal processes for plan enrollment. Perhaps assisting in the company’s visibility is its choice to open a satellite office in Des Moines in the middle of last year, to be closer to the global insurance industry. (Limelight’s headquarters are in the San Francisco area.)
Elon Musk, Tesla
Elon Musk, co-founder and chief executive officer of Tesla Inc., reacts while speaking during an unveiling event for the Tesla Model Y crossover electric vehicle in Hawthorne, California, U.S., on Friday, March 15, 2019. Musk said the cheaper electric crossover sports utility vehicle (SUV) will be available from the spring of 2021. The vehicle's price will start at $39,000, a longer-range version will cost $47,000. Photographer: Patrick T. Fallon/Bloomberg
The founder of electric and autonomous automaker Tesla has inspired and confounded executives across industries. His digitally enhanced line of luxury vehicles has spurred auto insurers to try an find the right products to fit it -- but expressing his dissatisfaction with the rates his customers have paid, Musk announced that Tesla would be launching its own insurance company this year. “It will be much more compelling than anything else out there,” Musk said of Tesla’s insurance product in an earnings call reported by Bloomberg. “We have direct knowledge of the risk profile of customers, and based on the car, and then if they want to buy a Tesla insurance, they would have to agree to not drive the car in a crazy way. Or they can, but then their insurance rates are higher.”
John Neal, Lloyds
John Neal, chief executive officer of Lloyd's of London Ltd., poses for a photograph following a Bloomberg Television interview in London, U.K., on Wednesday, March 27, 2019. Neal said Lloyd's of London is "firm" in its intention to stop sexual harassment in the workplace. Photographer: Luke MacGregor/Bloomberg
After just about half a year at the top job of one of the oldest insurance organizations on Earth, Neal is putting his stamp on Lloyd’s with a list of priorities that weigh heavily on the digital. Neal wants Lloyd’s to use advanced tech both to help place the hardest-to-insure risks -- with data boosting the ability for insurers to get the right price -- and the simpler ones, with automation making quick and effective decisions. He also will have to follow up on his predecessor Inga Beale’s insurtech accelerator project, which ran in the fall and early winter of 2018.
Jen Fitzgerald (pictured) and Francois De Lame, Policygenius
One of the earliest pure-play insurtechs, Policygenius has grown considerably from its early days in a Williamsburg, Brooklyn co-working space. The founders’ success, managed growth and McKinsey pedigree have contributed to their reputations as insurtech leaders. Fitzgerald and De Lame started out with the goal of improving the user experience for life insurance acquisition, but have since branched out to include auto and home insurance. (The company now also has its own office.)
Dogan Kaleli, Allianz
The specificity and need for innovation in the program business has led Kaleli to take a leadership role in Allianz’ insurtech efforts. But he has a unique perspective: In addition to being a long-time insurance executive, Kaleli is also a cofounder of multiple tech startups specializing in AI, quantum computing and digitalized ecosystems and mentors up-and-coming Turkish entrepreneurs through the Hamdi Ulukaya Startup Support Program. “When you have the AI abilities combined with quantum computing, you can better explain what’s going on with your level of income, your level of stress, these type of components traditional pricing results are not able to capture,” he says.
Dennis McKinley, Milk
Serial entrepreneur Dennis McKinley was first introduced to the insurance industry when he was approached by some larger insurers to open agencies. However, he said that considering the value proposition of insurance, there was a bigger opportunity to serve low-income and communities of color. So, he started Milk, an online broker live in all 50 states, with the goal of communicating to that market. Much of the tech infrastructure came through another insurtech, Bindable. “They are really popular in the affinity insurance business, and I thought, ‘What if i took that concept and targeted a demographic?’” McKinley explains. “We have to take a step further and talk about the benefits of having insurance.”
David Vogeleer (pictured), Charles Merritt, and James Paul, Buddy
The three founders joined to bring their business experiences to bear in a way that would help people with outdoorsy interests feel more secure in enjoying their hobbies. The result is Buddy, an episodic insurance product currently available through a network of partners, such as lift-ticket kiosks or intramural leagues like SportsEngine, via API technology, as well as on the company’s website. But the goal, its founders say, is to be a trusted partner for active people who turn their coverage on and off. That means the company is developing a digital conversational interface for its app so it can acquire more customers who aren’t necessarily going through a formal entrance to their activity.
Dan Peate, Avinew
A venture capitalist who had dabbled in health insurance with the startup Hixme, Peate also has decided to tackle high insurance rates for autonomous cars -- but after his experience buying a Tesla, not owning the company. Avinew, which launched in January 2019 with $5 million in seed funding, uses the data that comes from autonomous cars to give customers discounts. The goal, Peate told Bloomberg, is to bring the promise that autonomous cars are safer more in line with the insurance industry’s view of the vehicles.
Yogesh Shetty, Avibra
A former New York Life managing director, Shetty’s vision is for his new insurtech to offer “offer a Netflix-type subscription for overall well-being” which includes a life insurance component. By downloading the Avibra app, customers automatically receive $10,000 in term life insurance coverage from Amalgamated Life and Life of the South. After that, they can bump up the coverage by reviewing weekly in-app content, or by connecting connect their credit cards and bank account information, plus their wearables and other personal data sources, and opting into having that data reviewed by the company’s analytics engines.
Atul Gawande, Haven
When Amazon, Berkshire Hathaway, and JP Morgan Chase announced their intention to enter the healthcare sector, established companies were shaken by the potential disruption. Gawande, a former surgeon who is known for targeting the cost structure of healthcare in his writings and opinions, was tapped to lead the combined venture. “We will create new solutions and work to change systems, technologies, contracts, policy, and whatever else is in the way of better health care,” Gawande wrote in a letter posted at the time the company was named Haven. “We will be relentless. We will insure our work has high impact and is sustainable. And we are committed to doing this work for the long-term.”
Sally Poblete, Wellthie
Health insurtechs are closely observed due to the myriad groups with a vested interest -- including insurers, healthcare systems, employers and consumers. Wellthie, which Poblete started after spending time on the insurer side at Anthem, has gained notoriety for its platform that looks to ease access for all stakeholders. The company partnered with Beam Dental, known for its “smart toothbrush” and data-driven approach, to advance more effective dental coverage in small businesses. This year, it launched a marketplace platform to help small business owners review more plans in less time, leveraging analytics data to match the overwhelming amount of offerings to a business’s particular company profile.
Brandon Gell, Clyde
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Insurers are increasingly looking to partner with other vendors to leverage customers’ desire to protect new products. Gell believes that transforming insurance at the point of sale starts with the extended warranty industry. His company’s API and insurance partnerships offers businesses on turn-key e-commerce platforms such as Shopify a passive revenue source, by providing warranties via Clyde’s plug-in that integrates with an online store; matches products to contracts; and sets margins. It recently launched in-store capabilities to work within stores’ point-of-sale systems, in addition to a widget for companies that can’t leverage the API. The company was selected for Techstars’ accelerator this year.
Roberto Sicconi and Maggie Stys
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Both known as experts in conversational technology, Stys and Cicconi first collaborated on the digital language learning platform Telelingo. But their attention quickly turned to the distracted driving crisis facing modern drivers -- and insurers. Dreyev uses in-car cameras coupled with computer vision to create behavior models that anticipate upcoming risks and generate personalized urgency-triggered alerts in real-time for fleets and individuals -- all processed by the smartphones that most drivers already have with them. The company took third place at Quesnay’s inaugural Female Founders in Insurtech competition.
Yaron Ben-Zvi, Haven Life
Since launching as a subsidiary of MassMutual four years ago, Ben-Zvi’s Haven Life has operated in the gray area between insurtech startup and operating unit of a legacy carrier. But over the course of the past year, the company has carved out its own identity. It started with acquiring another insurtech, Quilt, with the goal of using that company’s platform to help it expand into annuities. The product line should launch this year. It also recently won the Model Insurer award from insurance consultancy Celent for its InstantTerm algorithmic underwriting process, which leverages a large amount of provided and third-party data to issue policies without a medical exam
Ron Glozman, Chisel
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Confronted with a pile of reading for a university literature class, Glozman did what many panicky students wish they could: He whipped up an AI program to do the reading for him and summarize the key points. That program has evolved into Chisel, a natural-language processing platform for commercial insurance. The company has ascended quickly in the insurtech world, winning ACORD’s 2018 Innovation Challenge and taking the gold prize at Zurich’s inaugural Zurich Innovation World Championship.
Tim Cunningham, Grange
Cunningham joined the Ohio-based P&C insurer in 2016 after ascending to the role of Managing Director & CTO at Chase, and has spent that time building a culture of innovation at the company that has included partnering with several insurtechs to modernize its offerings. The company rolled out Urgent.ly’s roadside assistance in fall 2018; it also has partnered with Truemotion and Octo on various telematics initiatives; and Terrene Labs leveraging big data and AI to identify and assess risks. Most recently, Grange has joined up with Rev1 Ventures to get better connected to emerging insurtechs through the G-Force Innovations initiative, which will identify, develop, and adopt emerging technologies.
Sastry Durvasula, Marsh
Since arriving from American Express in 2017, Durvasula has unleashed a torrent of innovation at the venerable brokerage. He has been particularly active in leveraging blockchain, leading a partnership with data-security company Evident to introduce a blockchain-based offering for clients in the sharing and gig economies and piloting an offering for proof of insurance along with IBM. Durvasula believes Marsh’s years of accumulated data on all aspects of risk can be unleashed with the right stewardship. He hired a global head of data science earlier this year, Andrew Hickman, late of Experian, and sees a big opportunity in small commercial. ìData is a strategic asset for Marsh and there is a humongous opportunity to disrupt,” he says.