Cover Whale

Cover Whale is an InsurTech company that specializes in commercial auto insurance for the trucking industry. Founded in 2019, it operates as a managing general agent (MGA) and utilizes technology, underwriting expertise, and data analytics to create tailored insurance programs. The company offers a comprehensive suite of products, including automobile liability insurance, trucking insurance, motortruck cargo insurance, and various liability coverages for different types of vehicles. The company emphasizes technology-driven solutions, featuring a proprietary driver safety program that incorporates telematics and real-time coaching to enhance road safety. This program rewards safe drivers with premium discounts of up to 30% after a year of safe driving. Cover Whale also provides a fast online quoting and binding experience, accessible to over 4,000 active insurance agents. With significant growth, the company has written over $1 billion in gross premiums and expanded its coverage to 41 states, with plans to reach 46 states. Cover Whale is recognized in the industry for its innovative approach and commitment to serving commercial truckers.

Insurance PECK SLIP, United States Founded 2019 ~104 employees

Work at Cover Whale in HR or recruiting? Claim this page

Employees
104
+2% in the 3 months to Jun 2025
Revenue / employee
$2.7M
Revenue ~$277M
Total funding
$83M
Last round Jul 2025
12-month attrition
27.2%
Tech: 34.4%
H1B filings, FY2025
1
Sponsors visas
Open jobs
1
Last 30 days

Headcount trend

Cover Whale went from 111 employees in Jul 2023 to 104 in Jun 2025. Jan to Jun 2025: 6 people joined, 9 left.

Headcount data through Jun 2025

Org structure

Headcount by department

Other50
Operations15
Sales12
Engineering7
Marketing5
Product5
Success4
Finance3

Hiring now

See all jobs

H-1B sponsorship

H-1B Sponsorship Limited
H-1B Filings by Department
Engineering2
Design1

The department split adds up all the years listed above. FY2025 alone: 1 filings.

Funding

  • Jul 2025 · $40M · Morgan Stanley Expansion Capital
  • May 2024 · Series A · $27.5M · Morgan Stanley Expansion Capital
  • Oct 2021 · Seed · $15.5M · Ambac Financial Group, Inc

Peer reviews

Worked with someone at Cover Whale?

Anonymous peer reviews on OffTheRecord

Read or write a review

Similar companies

Cover Whale FAQ

How many employees does Cover Whale have?

Cover Whale has about 104 employees, up 2% over the 3 months to Jun 2025.

Does Cover Whale sponsor H1B visas?

Yes. Cover Whale filed 1 H1B (LCA) application in FY2025, according to the latest U.S. Department of Labor disclosures. It was for a Design role.

What is Cover Whale's revenue per employee?

Cover Whale makes about $2.66M in revenue per employee, based on $277M annual revenue and 104 employees.

How much funding has Cover Whale raised?

Cover Whale has raised $83M in total funding.

Data from Company Prospectus, DOL LCA disclosures, WARN notices and 6figr salary profiles.