LEEO Insurance Services

LEEO Insurance Services

AI-powered, data-driven fleet auto insurance

Overview

LEE0 Insurance Services provides auto insurance for fleets using data and AI, offering a fleet dashboard, digital incident reporting, collision alerts, and data-driven claims to manage risk and reduce costs. Its platform analyzes fleet data to price risk, trigger proactive safety actions, and deliver faster claims processing, with performance-priced premiums that can decrease over time. It differentiates itself by tying premiums to ongoing performance, enabling monthly premium reductions, and by emphasizing a seamless broker experience backed by insurers rated AM Best A- or higher. The goal is to offer cost-effective, flexible fleet auto insurance that reduces risk, improves safety, speeds up claims, and simplifies insurance management for brokers and clients.

About LEEO Insurance Services

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

Get referred to LEEO Insurance Services

See people who can refer or advise you

Simplify Jobs

Simplify's Take

What believers are saying

  • LEEO launched March 25, 2026 telematics-powered products rewarding safe driving with cash back.
  • Coverage is backed by AM Best A-rated carriers, easing broker and fleet adoption.
  • Savings for Safety offers up to 10% cash back, a strong renewal hook.

What critics are saying

  • Broker distribution limits reach if appointed-channel growth stalls in 2026.
  • Appetites stay narrow: non-emergency medical transport, light business auto, and last-mile delivery.
  • Fairmatic's August 2025 strike-off scare exposed legal fragility; another filing lapse threatens survival.

What makes LEEO Insurance Services unique

  • LEEO rebranded from Fairmatic on December 15, 2025, keeping the telematics core.
  • Jeffrey Chen became CEO in August 2025, sharpening a broker-first commercial auto focus.
  • Mandatory telematics across every policy powers pricing, claims, and safety feedback loops.

Help us improve and share your feedback! Did you find this helpful?

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

0%

1 year growth

-26%

2 year growth

-19%
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.

Recently Posted Jobs

Sign up to get curated job recommendations

There are no jobs for LEEO Insurance Services right now.

Find jobs on Simplify and start your career today

We update LEEO Insurance Services's jobs every few hours, so check again soon! Browse all jobs →