Cover Whale welcomes Darryl Siry to spearhead technological advancements


The company highlighted Siry’s extensive background in technology strategy, operations leadership, and product innovation, positioning him to drive Cover Whale’s ongoing growth and enhance its technological capabilities.

Dan Abrahamsen, CEO of Cover Whale, expressed confidence in the impact of Siry’s appointment: “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 operationalise it for the benefit of our policyholders and agent partners.” 

Abrahamsen emphasised Siry’s expertise in the insurance and technology sectors, foreseeing it as instrumental in transforming the trucking insurance industry.

Siry himself articulated his enthusiasm for joining Cover Whale, recognising the company’s innovative approach to trucking insurance. He remarked: “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.” 

Siry sees the potential for Cover Whale to scale its business and become a trailblazer in the commercial transportation insurance sector.

Prior to joining Cover Whale, Siry held key leadership positions at notable companies in the insurance and technology industries. 

With the addition of Darryl Siry as the chief operating & technology officer, Cover Whale solidifies its position for continued success and growth in the insurance industry. The company’s commitment to leveraging technology for an efficient insurance platform is evident, with Siry’s appointment emphasising their dedication to innovation and customer-centric solutions.

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