Led · Seed · Oct 2021

Founded in 2020 and headquartered in New York, Cover Whale operates as a managing general agent (MGA) offering a proprietary technology platform that enables agents to quote and bind trucking policies online in minutes. The company leverages real-time telematics, continuous underwriting, AI-powered driver coaching, and other data sources as part of a driver safety program and real-time risk monitoring. Cover Whale says its platform delivers the industry’s fastest quote-and-bind experience while achieving industry-leading loss ratios in the commercial trucking segment. Since inception the firm has partnered with nearly 5,000 agents and written more than $1.3 billion in gross premium. Year to date Cover Whale reported $133 million of gross written premiums in the first half of 2025 and is on track for a full-year target of $277 million. The company plans to use new financing to accelerate investments in its technology platform, analytics, and expanded product offerings to drive growth and profitability. Cover Whale is an insurtech that provides connected insurance for commercial auto, focusing on the trucking sector through instant quotes and bound coverage. Launched in 2019, the company combines easy, instant quotes and binds with advanced telematics and real-time driver coaching. It announced $27.5 million in combined debt and equity financing from funds managed by Morgan Stanley Expansion Capital, with existing debt investors converting into Series A preferred. The company says the funding will create a strong balance sheet to support its profitable, growing business and accelerate its growth. Cover Whale plans to invest in its technology and operating platform to further improve speed to quote and service quality. Management frames the raise as part of its mission to transform commercial trucking insurance and improve road safety. Cover Whale is an insurtech MGA built on technology, data, and machine learning analytics to transform the commercial auto insurance segment. Its proprietary, technology-enabled platform provides instantaneous quotes from multiple carrier partners and leverages real-time data to underwrite and intervene on driver behavior. The platform is designed to correct negative driver behavior in real time to reduce loss ratios and lower overall insurance costs. Products are available exclusively through CoverWhale.com with capacity from multiple leading insurance markets. The company grew from five employees to over 80 employees and contractors in the past year and reported becoming cash-flow positive earlier in 2021. Founder and CEO Dan Abrahamsen said the company will use new funding to further invest in its proprietary platform and attract industry talent.