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Well Run profileThe Well Run 100 · #37 of 720

Position 37

Ledgebrook

AI-native specialty (E&S) insurer for mid-sized businesses, sold through wholesale brokers

Pace
3:30/kmSprint5.5
Distance
Distance 10K.
Open ops roles
4
Last week
—
Move
New
Peak
#35
Weeks in the 100
1
The Chart →
Rank and score over time
Board rank
#25#35#45#35Oct 25
Pace score
02465.5Oct 25

One point per Sunday re-rank, tracking since Oct 25. The lines fill in week by week.

Sprint 3:30/kmLedgebrook
Race 4:05/km
Tempo 4:40/kmCounterpart
Steady 5:20/km
Warm-up 6:00/km
Cool-down 6:30/km
Ledgebrook runs in the Sprint lane. Rivals on Well Run sit in their own pace lanes; further right = more momentum. Tap one to open its page.Also competes with: Kinsale Capital, Markel, Bishop Street Underwriters, RSUI
Revenue estimate
$100M+ annualized premium run rate (premium, not revenue)company-stated · as of Feb 2025 teardown.ai ↗
Total raised
~$315Msee rounds ↓
Headcount
~300as of Oct 2026 ledgebrook.com ↗
Founded
2022
HQ
Boston, MA

Leadership

The problem

Brokers wait weeks for quotes on complex, hard-to-place commercial liability risks and lose deals meanwhile

What they do

AI-native specialty (E&S) insurer for mid-sized businesses, sold through wholesale brokers

Traction On track for $1B cumulative premium since 2023; $100M premium run rate hit in 19 months

Hiring trend

Open roles
37
Ops roles
4
Headcount
~300

Headcount ~126 → ~274 Q1 2025 to Q1 2026 (Revelio, +117%); ~300 per company Oct 2026; postings +118% in 2026

Funding

Last round
$200M
Stage
Series D
Date
Oct 2026

Led by Allianz X, Rockefeller Capital Management

Distance

10K · edge: learns from use

Fast-growing tech-led E&S writer with its own A- rated carriers and Allianz capacity, but a small follower behind Kinsale, Markel and W.R. Berkley, and its long-tail casualty book has no published loss ratios yet.

Sources: Fortune: Ledgebrook $200M Series D, ~$2.6B valuation, ~300 staff (Oct 2026) ↗ · Teardown: Ledgebrook competitive set and skeptic case, no public loss ratios (Jul 2026) ↗ · Ledgebrook: $200M raise, AM Best A- carrier, ~$1B cumulative premium (Oct 2026) ↗

Last checked Oct 19, 2026

News timeline

  1. Oct 2026Raises $200M Series D co-led by Allianz X and Rockefeller; ~$2.6B valuation fortune.com ↗
  2. Oct 2026Allianz Re agrees multi-year reinsurance deal; on track for $1B cumulative premium ledgebrook.com ↗
  3. Sep 2026Named to CB Insights' 2026 list of 50 most promising insurtech startups ledgebrook.com ↗
  4. Aug 2026AM Best rates its carriers A- (Excellent), completing move to full-stack insurer news.ambest.com ↗
  5. Aug 2025Launches Ledgebrook Re, a reinsurance brokerage and advisory arm reinsurancene.ws ↗
  6. Jun 2025Closes oversubscribed $65M Series C led by The Stephens Group prnewswire.com ↗

Funding historyTotal raised ~$315M

  1. Oct 2026Series D$200Mat ~$2.6B post-money (Fortune, source close to company)Led by Allianz X, Rockefeller Capital Management fortune.com ↗
  2. Jun 2025Series C$65MLed by The Stephens Group prnewswire.com ↗
  3. Sep 2024Series B$17MLed by Duquesne Family Office, The Stephens Group prnewswire.com ↗
  4. Mar 2024Series A$24MLed by American Family Ventures teardown.ai ↗
  5. Apr 2023SAFE$4.6MLed by Markd prnewswire.com ↗
  6. Aug 2022Seed$4.2MLed by Brand Foundry Ventures teardown.ai ↗

Profile facts checked Oct 19, 2026. Every fact links to its public source.

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