August 2, 2018
40 Under Forty 2018

Matt Chesky

Photo | J. Fiereck Photography
Photo | J. Fiereck Photography

Age: 28

Company: Insuritas

Title: Chief Operating Officer

No. of years with current company: 6

Town where I live: West Hartford

Town where I work: East Windsor

College: Yale University

Highest degree: Bachelor's degree in economics

Matt Chesky is the chief operating officer of Insuritas, a leading insurtech company headquartered in East Windsor that operates virtual insurance agencies for financial institutions. Chesky joined Insuritas after graduating from Yale, and assumed the role of COO in 2016.

As COO, Chesky is responsible for driving growth and operating efficiencies in Insuritas' call center, managing its corporate development strategy in its core verticals and aligning investments in the company's technology platforms with overall corporate strategy.

Under Chesky's leadership, the company has achieved 40 perent-plus year-over-year recurring revenue growth and has become one of the fastest-growing insurtech companies nationally.

What's been the biggest professional accomplishment so far in your career?

In early 2018, I helped lead Insuritas to achieve one of our core corporate objectives by becoming one of the nation's 50 largest personal lines insurance distribution platforms. At a time in our industry when competitive pressures and shifting consumer expectations are driving consolidation and a loss in market share for agency distribution models, this achievement affirmed that by coupling strategic investments in technology with a relentless focus on our customer experience, we can deliver industry-leading revenue growth.

How are you involved in the community?

As a recent transplant to the Hartford area, I've found that one of the best ways to connect with other community-oriented professionals has been to engage in service opportunities sponsored by groups like FLOW and HYPE. As a former Division I soccer player, I also volunteer with a local youth soccer program to support children interested in pursuing a similar path.

What must the Greater Hartford region do to attract more talented young professionals to the area?

Greater Hartford must invest in attracting the types of businesses that can scale exponentially. That requires a concerted recruiting effort targeting startups, and investing in a robust support system (education/transportation infrastructure) to ensure they see Connecticut as a viable ecosystem in which to scale a business.

Four reasons why you deserve to be a 40 Under Forty:

• Scaled Insuritas' agency platform to become one of the 50 largest personal lines agencies in the country.

• Drove Insuritas' 100 percent growth in recurring revenue in 2.5 years since assuming COO role.

• Led development and implementation of Insuritas' SmartCART Technology, which was featured at FINOVATE, one of the nation's leading fintech events.

• Coordinated Insuritas' first foray outside of the financial institution vertical by launching Overstock.com Insurance for a leading international e-tailer.

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