# Thimble

> Thimble is a US commercial insurance platform for small businesses and independent professionals, arranging coverage by the job, month or year through carrier partners. Its app, website and broker tools handle quotes, purchases and policy administration. Arch Insurance acquired it in 2023.

- **Founded:** 2015
- **Headquarters:** New York, United States
- **Founders:** Jay Bregman (Co-founder; former CEO and President), Eugene Hertz (Co-founder and founding CTO)
- **Products:** General Liability, Professional Liability, Business Owners Policy, Business Equipment Protection, Workers’ Compensation
- **Notable:** Sold over 35,000 drone policies in less than two years after the 2016 Verifly launch, according to its help center., Delivered more than 170,000 small-business policies since May 2018 by the April 2023 acquisition announcement., Listed among Fast Company’s Most Innovative Companies and CB Insights’ Fintech 250 in 2021.

## Products & services

- **General Liability** — Coverage for covered third-party injury, property damage, and personal or advertising injury claims; available in on-demand, monthly and annual forms, subject to eligibility.
- **Professional Liability** — Errors and omissions coverage addressing covered financial-loss claims arising from professional services.
- **Business Owners Policy** — Annual coverage combining general liability and commercial property, with business interruption coverage and optional additions.
- **Business Equipment Protection** — Inland marine coverage for eligible equipment used for work.
- **Workers’ Compensation** — Access to coverage for work-related employee injuries and illness through partner offerings; availability varies.
- **Cyber Insurance** — Cyber coverage listed among broker offerings; eligibility and terms vary by insurer and state.
- **Special Event Insurance** — Event liability with an optional liquor liability component for eligible events.
- **Certificate Manager** — Free software for requesting, tracking and checking vendor insurance certificates against requirements.
- **Broker Portal** — Producer tools for quoting, binding and managing client policies and referral attribution.
- **Bold Penguin AI quoting integration** — Agent-to-agent connectivity supporting natural-language insurance quoting and binding workflows for producers.

## Achievements

- Sold over 35,000 drone policies in less than two years after the 2016 Verifly launch, according to its help center.
- Delivered more than 170,000 small-business policies since May 2018 by the April 2023 acquisition announcement.
- Listed among Fast Company’s Most Innovative Companies and CB Insights’ Fintech 250 in 2021.
- Reported nine consecutive quarters of growth under Arch in July 2025.

## Latest updates

- **2026-09** — Announced the Bold Penguin AI quoting integration on September 25.
- **2026-04** — Published expanded producer activity eligibility and coverage options.
- **2025-07** — Ian Westerman became President as Jay Bregman stepped down to pursue an opportunity outside insurance.

## Links

- Website: https://www.thimble.com/
- LinkedIn: https://www.linkedin.com/company/thimble/
- Twitter/X: https://twitter.com/thimble
- YouTube: https://www.youtube.com/channel/UCZu_DrFeVXBszKkhb2IrqZg
- Instagram: https://www.instagram.com/thimble/
- Facebook: https://www.facebook.com/ThimbleInsurance/

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Profile page: https://yespress.io/thimble
Published by YesPress — https://yespress.io
Last updated: 2026-10-03