Cover Whale strengthens leadership with new COO and CTO

Siry brings extensive experience in technology strategy, operations leadership, and product innovation, positioning him to drive Cover Whale’s continued growth and technological advancements.

In his new role, Siry will oversee Cover Whale’s day-to-day operations, providing strategic guidance and ensuring the smooth execution of the company’s initiatives. He will also spearhead the development and delivery of industry-leading insurance products and technology solutions tailored to the needs of policyholders and insurance agents.

“Darryl’s remarkable track record of leading technology transformations and implementing innovative solutions will reinforce our culture of growth and innovation,” commented Dan Abrahamsen, CEO of Cover Whale. “His deep expertise in the insurance and technology sectors will be invaluable as we continue transforming the trucking insurance industry. I am confident that Darryl’s leadership and strategic vision will further accelerate the scalability of our products and technology infrastructure, enabling us to deliver even greater value to our customers and partners.”

Before joining Cover Whale, Siry held key leadership positions at prominent companies in the insurance and technology industries. Most recently, he served as chief technology officer at SiriusPoint, where he played a pivotal role in driving technological advancements and enhancing operational efficiency. Siry also held leadership positions at ProSight Specialty Insurance, Tesla Motors, and Fireman’s Fund/Allianz.

“Cover Whale epitomises how technology can revolutionise the insurance landscape and create significant value for customers and agents,” remarked Siry. “Their innovative approach to trucking insurance, employing cameras, telematics, artificial intelligence, and a streamlined online experience, has resulted in an industry-leading loss ratio and an efficient underwriting process. I am thrilled to join Cover Whale’s team and contribute to their mission of transforming the commercial transportation insurance industry.”

Earlier this year, Cover Whale made a groundbreaking move by appointing the industry’s first chief artificial intelligence officer (CAIO). With the addition of Siry as the COO and CTO, the company further strengthens its commitment to leveraging technology to deliver exceptional customer service.