Cover Whale
Making commercial auto insurance faster, easier, and smarter for agents, policyholders, and the broader insurance ecosystem
Overview
Cover Whale is a technology-driven managing general agent (MGA) specializing in commercial auto insurance for the trucking and transportation industry. Founded in 2019 by experienced insurance and technology veterans, the company combines proprietary algorithmic underwriting with real-time telematics and driver coaching to deliver a faster, safer, and more profitable insurance experience.
Since its inception in 2020, Cover Whale has partnered with nearly 5,000 agents across 46 states and has written more than $1.3 billion in gross premium through its platform. The company booked $184 million in gross written premium for the full year 2024 and was on track for a $277 million full-year target in 2025, representing a strong growth trajectory while maintaining industry-leading loss ratios.
Cover Whale's unique approach integrates coverage with its DriveSmart safety program, which combines telematics, dash cams, and real-time driver coaching to reduce claims and improve road safety. The company has coached over 16,000 drivers and processes more than 200 daily automated risk assessments, positioning it as a leader in the connected commercial insurance space.
Products & Services
Commercial Auto Liability
Primary liability coverage for commercial trucking operations, available in 41 states. Cover Whale's algorithmic underwriting enables agents to quote and bind policies in as little as 18 minutes, compared to the industry standard of 2-5 days.
Key Features
- Instant online quoting and binding
- Algorithmic risk pricing
- Real-time continuous underwriting
- Available in 41 states
Target Users: Owner-operators and small-to-medium trucking fleets
Distribution: Wholesale and retail agents
Auto Physical Damage
Physical damage coverage for commercial vehicles, protecting against collision, comprehensive, and other physical damage losses.
Key Features
- Comprehensive and collision coverage
- Paired with liability for complete protection
- Fast quote-to-bind process
Target Users: Commercial trucking operations
Distribution: Wholesale and retail agents
Motor Truck Cargo
Cargo coverage protecting the freight being transported by insured truckers.
Key Features
- Freight protection during transit
- Various commodity classes covered
Target Users: For-hire trucking operations hauling goods
Distribution: Wholesale and retail agents
Non-Trucking Liability
Liability coverage for when commercial vehicles are being used for non-business purposes.
Key Features
- Personal use coverage
- Complements primary commercial auto policy
Target Users: Owner-operators using vehicles off-dispatch
Distribution: Wholesale and retail agents
Truckers' General Liability
General liability coverage for trucking operations beyond auto-related exposures.
Key Features
- Premises liability
- Operations liability
- Completed operations
Target Users: Trucking companies and owner-operators
Distribution: Wholesale and retail agents
DriveSmart Safety Program
A proprietary connected insurance program combining telematics, dash cams, and real-time driver coaching to reduce claims and improve road safety.
Key Features
- Real-time driver safety monitoring and coaching
- Over 16,000 drivers coached
- 200+ automated daily risk assessments
- Up to 15% premium discount on renewal for safe driving
- Dash cam integration
Target Users: All Cover Whale policyholders
Distribution: Included with Cover Whale policies
At a Glance
- Founded
- 2019
- Headquarters
- New York, New York
- Employees
- 51-200
Category & Focus
Last updated: 2026-03-25