Shift your career into high gear

CEO/Founder

"There's a long road ahead for commercial auto, and we are excited for the chance to help steer – faster solutions for agents, better rates for good drivers with free safety and coaching programs to help."

President

"With so many moving parts in the world of transportation, Cover Whale is using data-driven science and advanced technology to make our roads safer and save lives. We are dedicated to reducing accident frequency and improving insurance costs, and that is something I am passionate about."

Chief Revenue Officer

"Our agency partners are the lifeblood of our distribution strategy. I'm focused on building relationships that drive mutual growth—giving agents the tools, speed, and support they need to win in commercial auto while scaling our revenue profitably."

Chief Underwriting Officer

"At Cover Whale, we're leveraging decades of underwriting expertise with cutting-edge data science to transform how commercial auto insurance is priced and delivered. It's exciting to be part of a team that's bringing innovation to an industry ready for change."

Chief Actuary

"The opportunity to build actuarial models from the ground up, combining traditional insurance principles with real-time telematics data, is incredibly rewarding. We're not just analyzing risk—we're actively working to reduce it."

Chief Experience Officer

"Turning strategy into operational reality requires relentless coordination across underwriting, technology, and distribution. I work to ensure our teams move in lockstep—building processes that scale efficiently while keeping our customer experience fast and friction-free."

Chief Technology Officer

"Building a technology platform that powers real-time underwriting decisions for an entire industry is the kind of challenge that drives innovation. At Cover Whale, we're creating infrastructure that makes insurance faster, smarter, and more accessible."

Chief Financial Officer

"Building a profitable, sustainable insurance company requires both financial discipline and the courage to invest in innovation. At Cover Whale, we're proving that better underwriting and technology drive better economics—and I'm proud to help steer our financial strategy as we scale."

General Counsel & Corporate Secretary

"Insurance is one of the most regulated industries, but that doesn't mean innovation has to move slowly. My role is to clear the path—ensuring we stay compliant while moving fast to bring better products to market. It's a balance I find incredibly fulfilling."

Chief Architect

"Designing a system that can underwrite thousands of policies in real-time while continuously learning from telematics data is an architectural challenge unlike any other. At Cover Whale, we're building infrastructure that's both powerful and elegant."

Chief of Staff

"In a fast-growing company, alignment and execution are everything. I work across teams to ensure our strategic priorities translate into action—connecting the dots between product, operations, and growth so we move as one company."

Head of HR

"Cover Whale's success starts with our people. I'm passionate about building a culture where talented individuals can do their best work, grow their careers, and contribute to something meaningful—making transportation safer and insurance smarter."