Cover Whale

Shift your career into high gear.

Join the future of commercial trucking insurance.

Cover Whale has grown sustainably since our founding in 2019, and we’re looking for talented individuals to help us grow further and faster. And, our team is making our nation’s roads safer on a daily basis. Fact.

07/22/2026  
Who is Cover Whale? Cover Whale is the nation’s leading commercial trucking insurtech. We enhance road safety by integrating our insurance products with our telematics-based, data-driven driver coaching and safety program, DriveSmart. Our program is proven to save lives while delivering better insurance for our drivers. For more information, please visit www.coverwhale.com . The Role: We are rapidly expanding and looking to build a dynamic team of Regional Business Development professionals. The Business Development Associate will report to the Senior Business Development Manager, Team Lead, and support strategies to increase premium production in their region. This role involves managing smaller, established partners and newly onboarded partners, ensuring their successful integration and growth. The Associate will also develop strategies for these partner cohorts and provide key insights on their portfolio's makeup during quarterly reviews.  If you’re excited by...
Cover Whale New York, NY Full Time
07/14/2026  
Who is Cover Whale? Cover Whale is the nation’s leading commercial trucking insurtech. We enhance road safety by integrating our insurance products with our telematics-based, data-driven driver coaching and safety program, DriveSmart. Our program is proven to save lives while delivering better insurance for our drivers. For more information, please visit www.coverwhale.com . The Role: We are rapidly expanding and looking to build a dynamic team of Regional Business Development professionals. The Business Development Associate will report to the Senior Business Development Manager, Deputy Lead, and support strategies to increase premium production in their region. This role involves managing smaller, established partners and newly onboarded partners, ensuring their successful integration and growth. The Associate will also develop strategies for these partner cohorts and provide key insights on their portfolio's makeup during quarterly reviews.  If you’re excited...
Cover Whale Remote (OR) Full Time
07/08/2026  
Who is Cover Whale? Cover Whale is the nation's leading commercial trucking MGA. We improve road safety by combining the insurance products we sell with our telematics-based, data-driven driver coaching and safety program known as DriveSmart. Our program is proven to save lives while delivering better insurance for our drivers. For more information, please visit www.coverwhale.com .  Join us in the mission! The Role The Senior Compliance Manager is responsible for leading complex compliance activities, ensuring adherence to regulatory requirements, and providing expert guidance across the organization. This role oversees reporting, filings, and regulatory responses, including audits and consumer complaints, while developing and enhancing policies, procedures, and controls to support a strong compliance framework. This is a senior, cross-functional role that partners with internal teams to interpret regulations, mitigate risk, and drive strategic compliance initiatives...
Cover Whale Remote (United States) Full Time