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Rachel Olney, Kate Stillwell, and Hanna Wu.
Jana Ašenbrennerová
Three insurtech founders who are women discussed driving greater diversity and inclusion within the insurance industry.

Kate Stillwell, president, parametric insurance at Neptune Flood and founder of Jumpstart Insurance, which was bought out by Neptune in 2021 says that at the beginning of founding Jumpstart the team would get advice to start with a market that was more high net worth. "So, that was an intentional decision to disrupt that advice," she said during "Leading the Way: Women Insurtech Founders Panel," at Dig-In 2023 on June 6

There's a perception of insurance in America as a system that needs to be gamed, describes Stillwell. "It really conflicts with the larger purpose of insurance to provide this financial buffer. … Insurance empowers risk taking and is fundamental, foundational of being able to have courage in one's life. 

"So, how do we shift the script a little bit so that insurance starts becoming this thing that is more about that feeling of confidence as opposed to there's this thing that I have to deal with. We create our companies in a way that really supports and reinforces that mindset of this is actually a supportive tool for our financial stability and our generational growth. … Then those things like how we operate internally, how we hire and also how we communicate to the customers becomes this upward spiral that elevates the whole industry."

The panelists also discussed how to hire and retain employees. 

Hanna Wu, CEO of Amplify, said during the event: "We actually find people that don't have maybe even any experience in the field, sometimes they are the best because they're so driven to learn."

Wu says that attracting more women into the industry and helping the industry grow are two aspects that can be solved together. "More representation in leadership. I think it does take a little bit more effort from us who are already in the industry to create events. … It's an opportunity for us to step up and also relate more with people."

Rachel Olney, founder and CEO at Geosite, added that: "The thing that I've said to my team all the time is that a lot of times bias comes from under educating yourself on your biases and not doing the homework. So we consistently do that inside our company."


David Daniels and Jeff Tyler.
Jana Ašenbrennerová
"These are tools to enable people," says Jeff Tyler, head of product, data science and engineering at Two Sigma Insurance Qualified speaking at Dig-In on June 6, in a session titled, "How AI Can Help You Find and Keep Quality Talent." 

The session focused on how artificial intelligence can be useful in finding and retaining talent.

David Daniels, executive vice president and director of product development and innovation at MiniCo Insurance Agency, said that there is excitement and skepticism related to advanced technologies like AI. "We're spending time teaching and educating underwriters on how best to utilize that information."

Daniels shared that an underwriter recently started with the company and previously she had not done much with AI. "She can point and click and get all sorts of data and analytics on her desk so she can manage her book of business and get good insights without waiting for Excel spreadsheets to be prepared."

Daniels added that he believes that AI will revolutionize the way underwriters manage business and that will draw more people into the industry. 

"Underwriting attracts a lot of people into that field, it has so many areas in which to advance. I think it's a different and better way to do their job. … But no matter how much AI we bring into our industry, I believe there's always got to be a human in the loop, underwriting and verifying data. … I believe AI can mimic human behavior but it cannot create and AI is not in my opinion going to change how we interact with our agencies as far as those relationships."

Nestor Hugo Solari
Nestor Hugo Solari, founder and CEO of Sigo Seguros, an insurtech MGA, says that his background is primarily in finance and that he stumbled into insurance. Solari is from a Uruguayan family with relatives who didn't speak English, he said he was moved to start the company after seeing people struggle to get auto insurance.

"I started an agency in 2019 and started selling insurance over the phone. Now we're Sigo, which is the organization I founded." Solari said at Dig-In on June 6, in a session titled, "Insurance for the Underserved: How Thoughtful Products Can Help Immigrants and the Working Class." 

"I saw particularly an issue for Spanish speaking immigrants and working class communities in the U.S. for access to auto insurance. … I started looking into what are the challenges here? What are the challenges from the customer viewpoint," he said. "This is a prime example of how expensive it is to be low income in the United States, it's expensive to be poor. I think that's where you need to take advantage of the cost reduction aspect of technology."

Sigo uses telematics and a mobile-first insurance platform that focuses on not charging fees or using biased rating factors like credit scores and education level. Race and nationality are specifically excluded from being considered in insurance rating and underwriting, but geographic and educational standards can group customers into higher rate classes.

Solari added that diversifying the insurance workforce is essential: "One of the big legs up I have on most traditional insurance executives and big insurance companies is that I'm very familiar with the person I'm talking to on the other end of the phone. Latinos are the most underrepresented group amongst insurance executives in the United States. It's a lot harder to solve a problem for someone you've never met."

Customers can purchase insurance from Sigo in Spanish online and through its mobile app.

Kaitlyn Mattson
Managing Editor
Kaitlyn Mattson (she/they) is the managing editor of Digital Insurance. Kaitlyn covers a variety of topics related to insurance including risk,... Read full bio