Cover Whale bolsters AI capabilities with Darien Acosta at the helm


Cover Whale Insurance Solutions, an innovative commercial trucking insurance provider and leading InsurTech, has announced the appointment of its chief artificial intelligence Officer (CAIO), Darien Acosta. Acosta will take the lead of a newly-established AI Transformation division within the company.

Cover Whale, renowned in the industry for its utilisation of advanced AI and machine learning techniques, has been redefining the commercial trucking insurance space since its inception. The company has built a robust and efficient quoting and binding platform that has reshaped the sector. Additionally, the firm harnesses the power of AI/ML for its trailblazing Driver Safety Program, including real-time driver coaching and dashcam telematics integration.

The newly-appointed CAIO, Darien Acosta, has a storied career history in data science and analytics. Previously, he served as Cover Whale’s head of data analytics and, prior to that, he held the position of VP of Analytics at REEF Technology and head of data science at Barstool Sports, among others. Acosta’s wealth of knowledge and experience spans nearly two decades, making him a crucial asset to spearhead Cover Whale’s AI division.

Acosta joined Cover Whale in October 2022 and has since become an integral part of their analytics team. His leadership and proven track record will serve as a key driver in the adoption of AI and machine learning functions across Cover Whale, with the aim to provide tailored solutions to the company’s partner insurance agents and policyholders, and enhance all business functions.

In a statement, Cover Whale CEO Dan Abrahamsen emphasised the importance of AI to their growth, noting that the company is evolving its approach to AI from being an incremental addition to a core investment in business transformation. Acosta’s appointment is a testament to this, and he is anticipated to bring AI-driven processes and foster an AI culture across the company.

Acosta himself shared his enthusiasm about his new role and his vision for Cover Whale, stating, “I’m proud to take on this role and drive Cover Whale’s AI-first mission forward by investing in AI technology and staying ahead of the curve in the insurtech industry.”

The company recently earned the title of “Program Insurtech of the Year” by Program Manager/The Insurer. This accolade recognises Cover Whale’s innovative use of cutting-edge technology and its efforts to continually bring unique products to market, further solidifying its position as a leading force in the InsurTech space.

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