Verifly

On-demand insurance for drone pilots and small business owners -- flexible coverage from a single hour to a full year.

Specialty Solutions Growth Series A

Overview

Verifly is a New York-based insurtech company founded in 2016 by Jay Bregman (former CEO of Hailo) and Eugene Hertz (co-founder of Quidsi). The company pioneered on-demand, per-flight drone liability insurance through a mobile app, enabling drone pilots to purchase coverage in two taps with immediate activation. Policies covered a geographic radius around a chosen GPS location, making liability insurance accessible at the moment of need without annual commitments.

In 2019, building on strong product-market fit and demand to expand beyond drones, Verifly rebranded as Thimble and secured USD 22M in Series A funding led by IAC. Thimble now offers flexible, short-term business liability insurance across 140+ professions -- handymen, landscapers, photographers, DJs, cleaners, and gig workers. Drone-specific coverage through the Verifly app was discontinued in March 2023.

The legal entity remains Verifly Insurance Services, LLC, now a wholly-owned subsidiary of Arch Insurance Group Inc. Thimble continues active operations with app updates as recently as December 2025, underwritten by Markel Insurance Company.

Products & Services

On-Demand Drone Insurance (Verifly App -- Discontinued March 2023)

Verifly's original product enabled drone pilots to purchase third-party liability insurance on a per-flight basis through a mobile app. Coverage was available for recreational and commercial operators with no annual policy commitment.

Key Features

USD 1,000,000 third-party liability limit per flight
Geographic radius coverage (2-mile zone around a GPS location, up to 8 hours)
Pricing from USD 10/hour
Coverage for property damage, bodily injury, and unintentional privacy invasion from flyaways
Underwritten by Global Aerospace Insurance

Target Users: Recreational and commercial drone operators

Flexible Business Liability Insurance (Thimble Platform)

Following the rebrand, the Thimble platform provides on-demand business insurance across 140+ professions, purchasable by the hour, day, week, month, or year.

Key Features

General Liability Insurance
Professional Liability and Errors & Omissions Insurance
Business Owners Policies (BOP)
Commercial Property Insurance
Workers Compensation Insurance
Cyber Insurance
Event Insurance
Surety Bonds
Instant digital certificates of insurance
RESTful Partner API for embedding quotes and coverage in third-party platforms
Native iOS and Android mobile apps
Underwritten by Markel Insurance Company

Target Users: Small business owners, independent contractors, gig economy workers

At a Glance

Founded: 2016
Headquarters: New York, NY, USA
Employees: 11-50
Funding: Series A

Category & Focus

Category: Specialty Solutions
Subcategories: On-Demand Insurance Short-Term Liability Small Business Insurance Gig Economy Insurance
Insurance Verticals: P&C Commercial Specialty/E&S
Target Customers: Consumers, Agents/Agencies

Customers

Small business owners across photography, landscaping, cleaning, construction, fitness, and specialty trades
Independent contractors and gig economy workers