Cover Whale Appoints Chief AI Officer 

The commercial trucking insurance provider aims to become an ‘AI-first’ company, with the new position designed to spearhead the rapid adoption of AI company-wide.

(Image credit: Josie Farrow/Unsplash.)

In what it characterizes as an industry first, Cover Whale Insurance Solutions, Inc., a New York-based InsurTech MGA focused on commercial auto, has announced the appointment of its Chief Artificial Intelligence Officer (CAIO), Darien Acosta, who will lead a new AI Transformation organization within Cover Whale. Acosta’s team has a mission to fully leverage the new opportunities for automation, decision-making, and innovation that AI models and advanced algorithms enable, according to a Cover Whale statement. Previously serving as Cover Whale’s Head of Data Analytics, Acosta has joined the company’s executive team with the purpose of rapidly generating adoption of AI and machine learning functions across Cover Whale to generate customized solutions for its thousands of partner insurance agents and policyholders, and to accelerate all business functions, the company statement says.

Darien Acosta, Chief Artificial Intelligence Officer, Cover Whale.

Cover Whale reports that, since its founding, it has continually used AI and machine learning to build the fastest and easiest quoting and binding platform in the commercial trucking insurance industry. The company says it also leverages AI/ML to power its industry-leading Driver Safety Program, including consuming dash cam telematics and providing real-time driver coaching.

“AI and ML has allowed us to experience over 300 percent annual growth, which means we need to scale and enhance everything we do, now faster than ever before,” comments Dan Abrahamsen, CEO, Cover Whale. “We are doubling down on our existing AI efforts, and building an AI-first company. To be successful we’re fundamentally changing how we’ve considered AI, turning it from an incremental addition to existing tech infrastructure—the common practice in our industry—into a larger investment in core business transformation that will facilitate growth and scale. Darien has been an integral part of our analytics team and is a force to be reckoned with. He and his team will have authority to set AI priorities, make decisions and create new AI-driven processes, all while building the AI culture that’s critical to achieving scale in all aspects of our business.”

Dan Abrahamsen, CEO, Cover Whale.

Acosta, who joined Cover Whale in October 2022, previously served as VP of Analytics at REEF Technology (Miami), a SoftBank funded logistics startup. Prior to that, he was Head of Data Science and Audience Development at Barstool Sports, Head Of Analytics at Yahoo! Inc. and built the data department at Business Insider as an early employee. A seasoned executive with nearly two decades of leadership in data science and analytics, Acosta’s experience positions him firmly to lead Cover Whale’s AI journey and further drive growth and scale across the enterprise from Actuarial to Product to Customer Experience, the Cover Whale statement says.

“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,” comments Acosta. “As AI technology continues to evolve at a rapid pace, this is a prime time to leverage its potential to increase Cover Whale’s reach and presence, as well as provide our agents and policyholders with both cost and time-efficient services to keep them moving. I look forward to what’s in store both for us and the industry.”

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Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803.

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