Cover Whale Expands C-Suite with New Chief Operating & Technology Officer

Cover Whale Insurance Solutions, Inc., a leading commercial trucking insurance provider and fast-growing insurtech, has announced the addition of Darryl Siry as Chief Operating & Technology Officer. With an extensive background in technology strategy, operations leadership, and product innovation, Siry is poised to drive Cover Whale’s continued growth and enhance its technological capabilities.

In this role, Siry will be responsible for providing operational leadership, overseeing Cover Whale’s day-to-day operations. Additionally, he will drive the development and delivery of Cover Whale’s industry-leading insurance products and technology to meet policyholder and agent needs.

“Darryl’s impressive track record of leading technology transformation and execution will bolster our culture of growth and innovation, as well as our ability to operationalize it for the benefit of our policyholders and agent partners,” said Dan Abrahamsen, CEO of Cover Whale. “His expertise in the insurance and technology sectors will be instrumental in our ongoing efforts to transform the trucking insurance industry. I am confident that Darryl’s leadership and strategic vision will further drive the scalability of our products and technology infrastructure.”

Before joining Cover Whale, Siry held key leadership positions at prominent companies in the insurance and technology industries. Most recently, Siry served as Chief Technology Officer at SiriusPoint. Prior to that, he was Chief Technology & Operations Officer at ProSight Specialty Insurance where he led the technology, customer experience and operations functions of the company. He also held executive positions at Tesla Motors and Fireman’s Fund/Allianz.

“Cover Whale is the perfect example of how technology can drive insurance results and create value for customers and agents. Their unique approach to trucking insurance – leveraging cameras, telematics, AI and a streamlined online experience – results in an industry-leading loss ratio and efficient underwriting process,” said Siry. “The Cover Whale team has already built an impressive business in a very capital efficient way, and I look forward to helping them scale the business to another level and create the most successful commercial transportation insurance business the industry has seen.”

Earlier this year, Cover Whale appointed the industry’s first Chief Artificial Intelligence Officer. With the addition of Siry as the COO and CTO, Cover Whale is fortified for continued success and growth in the insurance industry. Siry’s appointment underscores the company’s commitment to leveraging technology to deliver the industry’s fastest and easiest insurance platform for agents, the best-fit, best-priced coverage for policyholders, and the most innovative driver safety enhancement programs available.