# Brian O'Reilly

> Brian O'Reilly is a seed investor at Greenlight Reinsurance backing Software. See 1 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [Greenlight Reinsurance](https://shizune.co/investors/profile/greenlight-reinsurance)
- Location: George Town, Cayman Islands
- Total investments: 1
- Last investment: Feb 2024
- Lead investor: 0%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/brianjoreilly/?originalSubdomain=ky

Brian O'Reilly is a seed investor at Greenlight Reinsurance in George Town focused on Software and Artificial Intelligence. Brian O'Reilly is the Head of Innovation at Greenlight Re.

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 1 | 100% |
| Artificial Intelligence | 1 | 100% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Armilla AI | Armilla AI is a governance platform that enables algorithmic accountability to drive ethical decisions with transparency.The platform utilizes algorithmic accountability for tracking and governance and allows models to be tested in a matter of hours, vetting both the models themselves and the underlying datasets, helping clients by providingcontinuous monitoring of ongoing performance, accuracy, and algorithmic accountability by detecting errors. | $4.5M | Seed | Feb 15, 2024 |  |

1 of 1 investments shown.

## Co-investors
- [Betaworks](https://shizune.co/investors/profile/betaworks) — VC Fund, 1 deal together
- [Chaucer](https://shizune.co/investors/profile/chaucer-9427) — VC Fund, 1 deal together
- [Mistral Venture Partners](https://shizune.co/investors/profile/mistral-venture-partners) — VC Fund, 1 deal together
- [Morgan Creek Digital](https://shizune.co/investors/profile/morgan-creek-digital) — VC Fund, 1 deal together
- [MS&AD Ventures](https://shizune.co/investors/profile/ms-ad-ventures) — VC Fund, 1 deal together
- [SixThirty](https://shizune.co/investors/profile/sixthirty) — VC Fund, 1 deal together

## About Greenlight Reinsurance

VC Fund · George Town, Cayman Islands

Greenlight Re (www.greenlightre.ky) is a specialist property and casualty reinsurance company based in the Cayman Islands and Ireland. The company provides a variety of custom-tailored reinsurance solutions to the insurance, risk retention group, captive and financial marketplaces. Established in 2004, Greenlight Re selectively offers customizedreinsurance solutions in markets where capacity and alternatives are limited. With a focus on deriving superior returns from both sides of the balance sheet, Greenlight Re's assets are managed according to a value-oriented, equity-focused strategy that complements the Company's business goal of long-term growth in book value per share.

4 contacts available at Greenlight Reinsurance.

| Name | Title | Profile |
| --- | --- | --- |
| Brian O'Reilly | Head Of Innovation | https://shizune.co/investors/profile/brian-o-reilly-05f0 |
| Neil Greenspan | Chief Financial Officer | https://shizune.co/investors/profile/neil-greenspan-6212 |
| Simon Burton | CEO | https://shizune.co/investors/profile/simon-burton-2d35 |
| Tom Curnock | Chief Risk Officer | https://shizune.co/investors/profile/tom-curnock |

## Similar investors

### Similar stage
- [Antler](https://shizune.co/investors/profile/antler-be9c) — VC Fund
- [Alumni Ventures](https://shizune.co/investors/profile/alumni-ventures-group) — VC Fund
- [Right Side Capital Management](https://shizune.co/investors/profile/right-side-capital-management) — VC Fund

## FAQ

### What does Brian O'Reilly invest in?

Brian O'Reilly invests primarily in Software and Artificial Intelligence startups, most often at Seed stage. Most of the 1 investments tracked by Shizune back companies in Canada. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### When did Brian O'Reilly last invest?

The most recent investment recorded for Brian O'Reilly closed in Feb 2024. Shizune tracks 1 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.

### Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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