Cover Whale expands legal scope with new GC hire

Rachel Dugan is taking the legal reins at Cover Whale, which aims to disrupt the commercial auto-insurance market.

Rachel Dugan previously worked at Indigo and SiriusPoint. (Courtesy image)

As the field for insurtech startups begins to narrow, those left standing are shoring up that business footing and looking at ways to scale up.

Enter Cover Whale Insurance Solutions, the startup aiming to disrupt the commercial auto-insurance market. The company announced that it has hired as its first general counsel, an in-house legal leader with extensive experience at traditional insurance carriers.

Rachael Dugan comes to New York-based Cover Whale from Nashville-based Indigo, an insurtech startup that provides professional liability insurance to medical groups, where she has been GC since October.

Before that, Dugan spent two years as chief legal officer of the New York-based reinsurer SiriusPoint, two years as general counsel and chief compliance officer of New York-based Reverence Capital Partners, which specializes in health care investments; and five years as associate general counsel of New York-based Marsh & McLennan, the giant risk manager and insurance broker.

Founded in 2019, Cover Whale says it provides commercial truckers with easy, instant quotes and relies on advanced telematics and real-time driver coaching to reduce risk. The company has raised $43 million in three funding rounds, including a $27 million debt-and-equity round announced this week provided by investment funds managed by Morgan Stanley Expansion Capital.

At Cover Whale, Dugan will lead all legal, compliance, corporate governance and regulatory affairs matters and will report to CEO Dan Abrahamsen.

“I’m thrilled to be joining Cover Whale, a pioneering insurtech transforming the commercial trucking space through technology and innovation,” Dugan said in a statement.

“With my experience leading the legal and compliance functions for large global businesses and building and scaling insurance businesses, I’m eager to help drive Cover Whale’s upward trajectory, reinforcing its commitment to innovation and driver safety.”

Dugan received her bachelor’s degree in biology from Loyola University and her law degree from Columbia University.

Before going in-house in 2013, she was an associate at Sullivan & Cromwell and a senior associate at Freshfields Bruckhaus Deringer.

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