LEEO Insurance Services

LEEO Insurance Services

AI-powered fleet auto insurance solutions

Overview

Fairmatic uses data and artificial intelligence to provide auto insurance for fleets, focusing on proactive risk management and driver safety. Its product includes a fleet dashboard with safety tips, digital incident reporting, collision notifications, and data-driven claims to help fleets cut costs and move faster after incidents. The company offers performance-priced auto insurance, where monthly premiums can decrease based on ongoing data-driven performance rather than staying fixed for a contract period. It also provides a seamless claims management service and a broker experience designed to simplify interactions for brokers and their clients. Coverage is underwritten by leading insurers rated AM Best A- or higher, giving fleets confidence. Overall, Fairmatic combines data, AI, and fleet-specific services to deliver cost-effective, flexible auto insurance for fleet businesses.

About LEEO Insurance Services

Simplify's Rating
Why LEEO Insurance Services is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Data & Analytics

Enterprise Software

AI & Machine Learning

Financial Services

Company Size

11-50

Company Stage

Series B

Total Funding

$88M

Headquarters

San Francisco, California

Founded

2019

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Simplify's Take

What believers are saying

  • December 2025 launch under Jeffrey Chen signals fresh execution and leadership discipline.
  • Telematics-driven pricing gives fleets monthly savings, a strong sales hook in 2026.
  • Reported $51.1 million ARR and 140 employees show meaningful commercial traction.

What critics are saying

  • Commercial auto losses stay volatile; one bad claims year can crush underwriting margins.
  • Founder Jonathan Matus stepped down in 2025, signaling strategic instability during the rebrand.
  • Fairmatic's 2026 identity shift from app.fairmatic.com to LEEO risks broker confusion.

What makes LEEO Insurance Services unique

  • LEEO, formerly Fairmatic, sells AI-underwritten commercial auto insurance for fleets.
  • December 2025 rebrand sharpened focus on telematics, faster quoting, and transparency.
  • Backed by Battery Ventures, Foundation Capital, and Aquiline Technology Growth.

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Funding

Total Funding

$88M

Above

Industry Average

Funded Over

2 Rounds

Notable Investors:
Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Above Average

Industry standards

$35M
$45M
Linktree
$46M
LEEO Insurance Services
$65M
Substack
$100M
ClickUp

Growth & Insights and Company News

Headcount

6 month growth

-81%

1 year growth

-6%

2 year growth

0%
Onfleet
Aug 28th, 2024
label Onfleet News Reduce Your Insurance Rate with Our New Onfleet - Fairmatic Integration 2 min read

Onfleet Inc. has partnered up with the vehicle insurance company, Fairmatic, to improve your understanding of your drivers' performance with a free driver analytic dashboard that can reduce your insurance rates based on that information.

Coverager
Feb 9th, 2024
Fairmatic Appoints Jim Hinchley As President Of Insurance

Commercial auto insurance startup. Fairmatic <i class="fa fa-info-circle company-popover" data-content="h3Fairmatic/h3. div

Insurance Insider
Feb 6th, 2024
Fairmatic brings on Hinchley as president of insurance

Fairmatic, a commercial auto InsurTech, has hired Jim Hinchley as president of insurance.

Calcalist Tech
Nov 19th, 2023
Appointment Fairmatic appoints Boaz Ram as Vice President of Product

Fairmatic, an insurtech startup that offers data-driven fleet insurance, has announced that it has appointed Boaz Ram as Vice President of Product.

Fairmatic
Mar 17th, 2023
Fairmatic Raises $46M to Drive AI Innovation in Commercial Auto Insurance

AI-powered commercial auto insurance company Fairmatic today announced it has raised $46 million in new funding, six months after its oversubscribed Series A, bringing its total financing to $88 million.

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