Ledger Investing

Ledger Investing is a New York-based, technology-led structurer and broker of casualty insurance-linked securities (ILS). It was founded in 2017 by Samir Shah — previously SVP and Head of Insurance Capital Markets at AIG — and went through Y Combinator. Its stated mission is to industrialise the transfer of US casualty insurance risk (workers' compensation, general liability, commercial auto, private passenger auto) from insurer balance sheets to institutional capital markets.

What Ledger actually is. This is not a piece of software a carrier buys. It is an ILS broker-dealer-plus-structurer: Ledger originates casualty portfolios from insurers, MGAs and fronting carriers, wraps them into Cayman-domiciled SPCs (Ledger Re SPC) and funds (Nanorock Fund Ltd., 2021), places the notes with institutional investors, and earns structuring and brokerage fees. The core regulated entities are Ledger ILS Managers, LLC (investment advisor) and Ledger Capital Markets, LLC (broker-dealer). A reader shopping for reinsurance-stack software should know that Ledger Investing is a capital-markets intermediary, not a tool they can license — Ledger spun its internal technology stack out as a separate SaaS subsidiary, Korra, in December 2025 to address that product surface.

Funding. Cumulative disclosed funding is approximately $95m across three rounds. A $5m seed in 2017 included AMWINS and MassMutual Ventures. A $10m Series A in September 2020 was led by Allegis Capital with MassMutual Ventures, SignalFire, Accel and Crosscut. A $75m Series B in June 2022 was led by WestCap with participation from Teachers' Venture Growth, Intact Ventures, SignalFire, MassMutual Ventures, Allegis and Accel. Peter Hancock, former AIG president/CEO, sits on the board.

Traction. Ledger closed its first transaction in 2019. By December 2024 it had surpassed $2bn in casualty ILS placed with institutional investors. By the December 2025 Korra launch the internal figure disclosed was 170+ transactions representing $7bn in gross written premium structured and serviced. Landmark deals include the first casualty ILS secondary trade, a $250m syndicated secondary to three institutional investors, and a $100m three-year quota-share sidecar for an unnamed global reinsurer funded in September 2024. In August 2024 Ledger transferred management of its casualty ILS funds to Fermat Capital Management, with Ledger retaining origination, structuring and servicing.

Why the technology matters (and where it stops). The casualty ILS market has historically been considered impractical because loss emergence patterns are long-tailed, opaque and hard to model — the opposite of the property-cat ILS world Fermat and others built after Hurricane Andrew. Ledger's pitch is that standardised data pipelines, actuarial modelling and contract tooling make casualty risk investable for institutional capital at scale. The Korra SaaS spin-out exposes four components publicly — Marketplace, Analytics, Reports and Contracts — with AI-driven contract extraction and bordereaux ingestion. None of this removes the underlying constraint: casualty losses develop over years, and an audited loss-ratio track record on Ledger-structured deals is not public.

Counterparty opacity. No ceding insurer, MGA or reinsurer has been publicly named in Ledger's primary announcements. The $100m sidecar names only "a global reinsurer"; the Nanorock Fund names only "a large pension plan". This is standard for ILS placements but means external validation of the book relies on Ledger's own disclosure plus Fermat's fund-level reporting.

Analyst gap. No Gartner, Celent or Forrester coverage surfaced. Sourcing is Artemis.bm (the gold-standard ILS trade publication), Reinsurance News, The Insurer, Carrier Management and Ledger's own press.