Cover Whale is an insurtech founded by experienced insurance and technology veterans that focuses on technology, underwriting, and data to provide innovative insurance programs for the commercial auto industry. Pulse 2.0 interviewed Cover Whale Chief AI Officer Darien Acosta to learn more about the company.
Darien Acosta’s Background
Acosta’s journey with Cover Whale began in October 2022 when he joined the company as the Head of Data Analytics. And Acosta said:
“Prior to Cover Whale, I led analytics efforts for more than a decade with the likes of Reddit, Yahoo! Finance, INSIDER, Conde Nast, and REEF. One of my early career milestones was establishing Business Insider’s (now INSIDER) data department as one of its initial team members. Having always had a deep passion for all things data and diving deeper into analytics and AI, joining Cover Whale to become the industry’s first-ever Chief AI Officer seemed like a natural next step in my professional path.”
“As Chief AI Officer, my primary responsibilities revolve around harnessing the transformative capabilities of AI models and advanced algorithms. The goal is to drive automation, enhance decision-making processes, and foster innovation by facilitating the widespread adoption of AI, ML, and generative AI across Cover Whale. This entails creating tailored solutions to meet the unique needs of our extensive network of partner insurance agents and policyholders.”
Solving Problems With AI
What specific challenges does Acosta believe AI can address in the trucking insurance industry? Acosta shared:
“For a particularly slow-to-adopt-technology industry like insurance, AI is a game-changer. Above all, when it comes to commercial trucking insurance, AI can help address unsafe driving behaviors among both truck drivers and those with whom they share the road, collect and assess that information and provide a clear path forward in terms of coaching.”
“We believe that safe drivers should be rewarded and not punished in order to compensate for the bad driving habits of others. Cover Whale’s ability to collect and analyze telematics data to create safer drivers and roads improves daily as we further scale our AI capabilities.”
Evolution Of Cover Whale’s Technology
Knowing Cover Whale has utilized AI/ML since its inception, how has your role influenced its continued evolution? Acosta noted:
“Cover Whale’s AI department aims to accelerate all aspects of business operations, from Billing to Claims to Engineering. It’s very exciting leading Cover Whale’s AI-first mission by investing in cutting-edge AI technology, ensuring that we remain at the forefront of the rapidly evolving insurtech landscape. This commitment to AI enables us to extend our reach, bolster our industry presence, and provide our agents and policyholders with efficient, cost-effective services.”
Challenges Faced
Has Acosta faced any specific bottlenecks with AI recently? If so, what were they, and how did you navigate these challenges? Acosta acknowledged:
“Not being able to move fast enough. We want to move as fast as the ideas are generated and leverage the technology that exists today. But there are AI technologies and applications that exist as research in R&D labs that are applicable to business but have not made it to market yet. This creates an awkward dynamic on what we should prioritize in terms of development.”
“For example, if we want to build AI-powered OCR functionality into our processes, do we build this internally or wait for an open-source, generative AI version to be released? To navigate these challenges, we seek to build processes that are modular so that we can easily swap out AI models that are redundant and swap in the latest and greatest AI tech at a later date… like upgrading a physical computer with a new chip.”
Differentiation From The Competition
What differentiates Cover Whale from other insurtechs? Acosta affirmed:
“Cover Whale is an MGA functioning as a high-growth insurtech and commercial trucking insurance provider. Our bread and butter is utilizing AI and ML to enhance driver safety through our unique Driver Safety Program, which mandates the use of dashboard cameras and leverages telematics to provide real-time coaching for truck drivers.”
“Normally, a company would need to build new processes and hire many different specialists to accommodate the growth and scale Cover Whale has been able to achieve. However, with an AI-first mentality, we are able to be more efficient with resource allocation.”
Core Products
Can you speak more to Cover Whale’s key products and features? Acosta explained:
“Cover Whale focuses on technology, underwriting, and data to provide innovative insurance programs for the commercial trucking industry. We deliver our products through more than 6,000 agents with the industry’s fastest, most agent-friendly online quoting and binding experience. Currently, Cover Whale offers a comprehensive line of coverages for independent truckers and fleet owners, including auto liability, physical damage, cargo and other policies, such as hotshots and Intermodal Interchange and Facilities Access Agreement (UIIA) coverage.”
Significant Milestones
What have been some significant milestones that your department has contributed to? Acosta cited:
“We were very early in the GenAI/LLM/ChatGPT revolution. We recognized this paradigm shift and moved quickly to deploy API-based generative AI technology throughout the organization while the world was still treating generative AI as a novelty. Because of this, Cover Whale has been able to make strides in adopting an AI-first approach to all aspects of work and have made it a part of our culture.”
Staying Updated On AI Advancements
How do you stay updated on the latest advancements in AI and ensure that your team is equipped with the most current tools and knowledge in this rapidly evolving field? Acosta pointed out:
“AI is a passion for me. It is the realization of dreams I had as a young boy reading science fiction in a small apartment in Brooklyn. Thus, I am constantly communicating and networking with researchers who are building the future of AI. Whenever people ask me the best ways to stay up to date, I tell them that my recommendation is to set up an account on X (formally Twitter), specifically for AI, and only follow AI researchers and VCs on that account. In this way, you will be a part of the communication that is carving the future.”
Plans For 2024
Is there anything exciting in the pipeline for Cover Whale in 2024? Acosta highlighted:
“To build upon our AI trajectory, we have launched our own AI chatbot called Bob, which stands for ‘Bundle Of Bots’. As an embodiment of expert knowledge and agility, Bob will streamline communication with agents and policyholders, crucially improving response times and supporting Cover Whale’s rapid growth. The chatbot is primed to handle a spectrum of queries originating from Cover Whale’s expanding base of commercial trucking insurance constituents, including insurance agents and their independent trucker and fleet-owner clients. Distinguished by accuracy and dynamism, Bob swiftly handles inquiries, including claims processing, quoting and binding status, loss runs, underwriting guidelines, and other inbound questions and the conversations that follow – in under two minutes.”
Favorite Memory
What has been your favorite memory working with Cover Whale so far? Acosta concluded:
“I can’t pin this answer down to a single favorite memory. But, I will say that my favorite moments are the many times when I can witness the wonder and awe that people express when my team can deliver and showcase a new tool or feature that makes their lives easier and that they never imagined possible. That is what makes Cover Whale wonderful for me.”
