Leading commercial trucking insurance provider will transition to being an AI-first business, with a new job created to lead the rapid adoption of AI throughout the whole organization.
A prominent supplier of commercial transportation insurance and a rapidly expanding Insurtech, Cover Whale Insurance Solutions, Inc., today announced the hiring of Darien Acosta as its Chief Artificial Intelligence Officer (CAIO). Acosta will head a new AI Transformation unit inside Cover Whale. The goal of Acosta’s team is to fully take advantage of the new possibilities for automation, judgment, and creativity that cutting-edge algorithms and AI models open up. Acosta, who previously held the position of Head of Data Analytics at Cover Whale, joins the executive team with the goal of accelerating all business operations while accelerating the adoption of AI and machine learning functions throughout Cover Whale to produce customized solutions for its thousands of partner insurance agents and policyholders.
Since its founding, Cover Whale has continuously incorporated AI and machine learning to create the quickest and most straightforward platform for binding quotes and coverage in the commercial trucking insurance sector. Additionally, the firm uses AI/ML to support its industry-leading Driver Safety Program, which includes telematics from dash cams and real-time driver instruction.
“We are currently growing by over 300 percent annually thanks to AI and ML, which means we must scale and improve everything we do more quickly than before. We are stepping up our current AI initiatives and creating an AI-first business,” according to Cover Whale CEO Dan Abrahamsen. “To be successful, we’re fundamentally altering the way we’ve thought about artificial intelligence, moving away from the industry-standard practice of seeing it as a small investment in core business change that will aid in growth and scale. Darien is a formidable member of our analytics team and has been a key contributor. In addition to developing the AI culture that is essential to reaching scale in all facets of our business, he and his team will have the authority to define AI priorities, make decisions, and design new AI-driven processes.”
Acosta previously held the position of VP of Analytics at REEF Technology, a logistics startup backed by SoftBank. Acosta joined Cover Whale in October 2022. Before that, he served as Head of analytics Science and Audience Development at Barstool Sports, Head of Analytics at Yahoo! Inc., and an early employee who helped establish the analytics division at Business Insider. Acosta, a seasoned executive with nearly two decades of expertise in data science and analytics, is well-positioned to steer Cover Whale’s AI initiative and further drive development and scalability throughout the whole organization, from actuarial to product to customer experience.
Acosta stated, “I’m honored to take on this job and advance Cover Whale’s AI-first vision by investing in AI technology and being at the forefront of the insurtech market. With the rapid advancement of AI technology, now is a great time to take advantage of its potential to expand Cover Whale’s presence and reach, as well as to offer our agents and policyholders cost- and time-effective services to keep them moving. I’m excited about what the future holds for the industry as a whole and for us.”
In recognition of its contributions to the program insurance industry, Cover Whale was also recently voted “Program Insurtech of the Year” by Program Manager/The Insurer. The prize honors the insurtech that has most convincingly shown how they use cutting-edge technology to promote novel products. The seamless integration of technology into Cover Whale’s operational model and strategy, ongoing research into new coverages, and investment in cutting-edge AI models all contribute to the company’s leadership position in the insurtech industry. This accomplishment highlights the company’s ongoing commitment to innovation as well as the teamwork of its employees, agency partners, and policyholders.