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Cover Whale

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An InsurTech that uses data and technology to provide a trucking platform that streamlines the application and quoting process

New York City, United StatesFounded 2019Fintech
Valuation $100–250M Last recorded · 2025
Revenue $10–50M Latest reported FY
Headcount 100–500 Current team size
Total funding $50–100M Disclosed equity funding
Unlock exact values This page shows ranges. Dealroom has the exact numbers for Cover Whale and the history behind them.

About Cover Whale

Cover Whale is a startup that operates in the commercial auto insurance market, specifically catering to the trucking industry. The company offers a comprehensive range of insurance products to truckers, covering various aspects such as liability, cargo, vehicle, and other associated risks. The target clientele includes both individual truck owners and small fleet operators who prioritize safety.

Cover Whale's business model is unique as it leverages artificial intelligence (AI) and telematics to enhance driver safety. The company's real-time driver safety coaching program, powered by AI, has been proven to reduce unsafe driving actions by 50%. This not only ensures safer roads but also helps truckers maintain a clean driving record, which can lead to lower insurance premiums.

The company works closely with a select group of insurance agents who are committed to finding the best and most affordable insurance coverage for their trucking clients. Cover Whale also offers a user-friendly quoting platform for agents, enabling them to provide instant quotes and thereby improving their productivity.

Cover Whale's revenue primarily comes from the premiums paid by the truckers for the insurance coverage. The company also offers specialized insurance products such as hotshots coverage and UIIA coverage for truckers hauling freight out of U.S. ports.

In summary, Cover Whale is a tech-driven insurance startup that offers comprehensive and affordable insurance solutions to the trucking industry, with a strong emphasis on driver safety.

Source: Dealroom company data

At a glance

Status
Operational
Founded
2019
Headquarters
New York City, United States
Employees
107
Open positions
3
Dealroom signal
68.2/100
Industry
Fintech, Transportation
Sub-industry
Insurance, Logistics & Delivery
Sector
Fintech, PandC Insurance, Vehicle Insurance, MGA
Technology
Artificial Intelligence
Business model
Marketplace & ecommerce
Client focus
b2b, b2c

Funding history

5 recorded events

Company financing events and reported valuations.

Deal typeDateAmountValuationInvestorsSource
EARLY VCOther financing Jul 2025 $40M $160M Morgan Stanley Expansion Capital ↗
DEBTDebt May 2024 $14M — Undisclosed ↗
Showing the latest 2 of 5 recorded eventsBook a demo for the full funding history →

Financials

Revenue over time

Revenue, earnings and other financial measures where available. Years marked “E” are estimates.

YearRevenueGrowth
2026
2025
2024
2023
2022
2021 —
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Growth signals

Cover Whale website traffic

Latest recorded traffic for Cover Whale is 55K monthly website visits, down 30.4% over the last three months. Cover Whale's team grew 9.2% over the past year.

Latest monthly visits55K 3-month web change-30.4% 1-year team growth+9.2%
Summary metrics are public; monthly history is available with a demoCompare with peers →

Similar companies

Closest operating peers by Dealroom taxonomy

Company identity and context are open; selected comparison metrics preview what is available on the platform.

Showing 8 of the closest matchesCompare every metric →

Investments and acquisitions

Capital deployed

Recent portfolio relationships for companies that also act as investors or acquirers.

Investors

3 investors on the cap table

From Dealroom's funding and investor records, grouped by the round each investor first entered.

Seed2 investors entered at this stage

  • TigerRisk Partners
  • Ambac Assurance Corporation (Formerly American Municipal Bond Assurance)

Series A1 investor entered at this stage

  • Morgan Stanley Expansion Capital
Team profiled 10 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 5 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
8 countries with
team presence
🇺🇸 United States88.6%
🇵🇭 Philippines2.5%
🇹🇷 Turkey1.3%
🇪🇬 Egypt1.3%
🇦🇺 Australia1.3%
Top 5 of 8 shown

Market sentiment

Posts on X, past 7 days

An AI-synthesised read of the highest-engagement posts about Cover Whale on X, ranked by likes and reposts, corporate channels excluded.

Reading the room on X — pulling top posts and synthesizing themes…

Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour

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