Commercial auto & trucking insurtech

Trucking is where telematics rewrote underwriting. These insurers price fleets on how they actually drive — real-time safety data feeding upfront discounts, monthly premium adjustments, or continuous driver coaching. Research profiles with rating status and key facts side by side.

Ratings are not yet published under methodology v2.1. Tap any company for the full profile, or read the ratings methodology.

Cover Whale

Best for: Single trucks and small-to-mid fleets whose agent wants fast binding plus driver coaching
Backing: $27.5M Series A (2024, Morgan Stanley Expansion Capital) + a ~$40M growth round (2025, MSEC)
Key coverage: Commercial Auto (trucking), Motor Truck Cargo, General Liability (trucking)
Availability: 46 states, via ~5,000 brokerage agencies

HDVI

Best for: Mid-size trucking fleets that want telematics-based, monthly-adjusting premiums
Backing: ~$70M+ raised across rounds; investors include Munich Re Ventures, Weatherford Capital, 8VC, Autotech Ventures
Key coverage: Commercial Auto (fleet), Motor Truck Cargo, General Liability (fleet)
Availability: US trucking fleets

LEEO

Best for: Brokers placing commercial auto for medical transport, light business auto, and last-mile fleets
Backing: As Fairmatic: $46M Series B led by Battery Ventures (2023); ~$88M total reported
Key coverage: Commercial Auto (medical transport, light business auto, last-mile)
Availability: US, via appointed brokers

Nirvana

Best for: Owner-operators and fleets that want telematics-based pricing and fast, modern claims
Backing: $100M Series D at a ~$1.5B valuation (2025, led by Valor Equity Partners); prior $80M Series C (2025)
Key coverage: Auto Liability, Auto Physical Damage, General Liability +1 more
Availability: US trucking (owner-operators and fleets)

Company	Best for	Backing	Key coverage	Availability
Cover Whale	Single trucks and small-to-mid fleets whose agent wants fast binding plus driver coaching	$27.5M Series A (2024, Morgan Stanley Expansion Capital) + a ~$40M growth round (2025, MSEC)	Commercial Auto (trucking), Motor Truck Cargo, General Liability (trucking)	46 states, via ~5,000 brokerage agencies
HDVI	Mid-size trucking fleets that want telematics-based, monthly-adjusting premiums	~$70M+ raised across rounds; investors include Munich Re Ventures, Weatherford Capital, 8VC, Autotech Ventures	Commercial Auto (fleet), Motor Truck Cargo, General Liability (fleet)	US trucking fleets
LEEO	Brokers placing commercial auto for medical transport, light business auto, and last-mile fleets	As Fairmatic: $46M Series B led by Battery Ventures (2023); ~$88M total reported	Commercial Auto (medical transport, light business auto, last-mile)	US, via appointed brokers
Nirvana	Owner-operators and fleets that want telematics-based pricing and fast, modern claims	$100M Series D at a ~$1.5B valuation (2025, led by Valor Equity Partners); prior $80M Series C (2025)	Auto Liability, Auto Physical Damage, General Liability +1 more	US trucking (owner-operators and fleets)