# Helen Sayles

> Helen Sayles is a seed investor in Concord backing FinTech, InsurTech and Financial Services. See 2 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Location: Concord, United States
- Total investments: 2
- Last investment: Mar 2021
- Lead investor: 0%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/helen-sayles-3449ba3/

Helen Sayles is a seed investor in Concord focused on FinTech and InsurTech. Helen Sayles is the President of Entrepreneurial Scotland Foundation USA.

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| FinTech | 1 | 50% |
| InsurTech | 1 | 50% |
| Financial Services | 1 | 50% |
| Property Insurance | 1 | 50% |

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 1 | 50% |
| Pre-Seed | 1 | 50% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Surround Insurance | Surround Insurance is an InsurTech company that offers property and casualty insurance products for young urban professionals. The company was founded in 2018 by Jonathon Grayson and Kate Terry and is headquartered in Cambridge, Massachusetts, United States. | $2.6M | Seed | Mar 23, 2021 |  |
| Surround Insurance | Surround Insurance is an InsurTech company that offers property and casualty insurance products for young urban professionals. The company was founded in 2018 by Jonathon Grayson and Kate Terry and is headquartered in Cambridge, Massachusetts, United States. | $1.4M | Pre-Seed | Dec 31, 2019 |  |

2 of 2 investments shown.

## Co-investors
- [Cameron Ventures](https://shizune.co/investors/profile/cameron-ventures) — VC Fund, 2 deals together
- [Plug and Play](https://shizune.co/investors/profile/plug-and-play-ventures) — VC Fund, 2 deals together
- [Sure Ventures](https://shizune.co/investors/profile/sure-ventures-4b28) — VC Fund, 2 deals together
- [Bantam Group](https://shizune.co/investors/profile/bantam-group) — VC Fund, 1 deal together
- [MassMutual](https://shizune.co/investors/profile/massmutual) — VC Fund, 1 deal together
- [MassMutual Impact Investing](https://shizune.co/investors/profile/mass-mutual-catalyst-fund) — VC Fund, 1 deal together

## Similar investors

### Similar industry
- [MS&AD Ventures](https://shizune.co/investors/profile/ms-ad-ventures) — VC Fund
- [Anthemis](https://shizune.co/investors/profile/anthemis-group) — VC Fund
- [Everywhere Ventures](https://shizune.co/investors/profile/everywhere-ventures) — VC Fund

### Similar stage
- [Antler](https://shizune.co/investors/profile/antler-be9c) — VC Fund
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### Similar country
- [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
- [General Catalyst](https://shizune.co/investors/profile/general-catalyst-partners) — VC Fund

## Featured in investor lists
- [InsurTech Angel Investors](https://shizune.co/investors/insurtech-angel-investors)
- [InsurTech Angel Investors in United States](https://shizune.co/investors/insurtech-angel-investors-united-states)

## FAQ

### What does Helen Sayles invest in?

Helen Sayles invests primarily in FinTech, InsurTech and Financial Services startups, most often at Seed and Pre-Seed stage. Most of the 2 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### When did Helen Sayles last invest?

The most recent investment recorded for Helen Sayles closed in Mar 2021. Shizune tracks 2 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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