What Thimble does

Thimble (legal entity Verifly Insurance Services, LLC) is a digital small-business insurance platform founded in 2016 in New York, operating as a wholly owned subsidiary of Arch Insurance Group Inc. (part of Arch Capital Group Ltd., NASDAQ: ACGL) since its April 2023 acquisition. The company sells commercial liability and property coverage - general liability, professional liability/errors & omissions, Business Owners Policy, commercial property, workers' compensation, business equipment protection (inland marine), cyber, commercial auto, event insurance, and surety bonds - through a proprietary web and mobile (iOS/Android) platform that issues quotes, binds policies, and delivers Certificates of Insurance in minutes, with flexible coverage durations ranging from hourly and daily gig/event policies to monthly subscriptions and annual plans.

The product is purpose-built for micro-SMBs, freelancers, contractors, and gig-economy workers across 1,000+ professions, with 75% of customers being first-time business insurance buyers. Thimble partners with multiple A-rated insurance carriers (Markel Insurance Company, National Specialty Insurance Company, Employers Insurance Group, Benchmark Insurance Company, Spinnaker Insurance Company, Coterie Insurance Agency) as the underwriting and capacity backbone, while monetizing through premium commission/agency economics and a usage-based pricing model that lets customers pay by the hour, day, month, or year. Go-to-market combines product-led growth (direct website and app), an Impact Radius affiliate program ($30 per qualified lead), a broker distribution layer (Thimble Widget, API, Certificate Manager), and a partnership as the 'Official Insurance of Angi' (formerly Angie's List).

The organization is 100% remote and small (11-50 employees), and has bound 250,000+ policies covering 151,000+ small businesses since 2018. Following the founder Jay Bregman's departure in July 2025, Ian Westerman (ex-Pie Insurance, previously Thimble SVP of Finance) leads the company as President during its ninth-consecutive quarter of growth under Arch Insurance North America. The platform holds A+ BBB accreditation, a 4.2-4.7/5 Trustpilot rating from 2,300+ reviews, and recognition from Fast Company (Most Innovative Companies 2021, Best UX Design 2021), CB Insights (Fintech 250, 2021), and Lloyd's (2020 accelerator cohort).

Name

Thimble

Legal name

Verifly Insurance Services, LLC

Website

https://thimble.com

Company type

Private

Founded year

2016

Operating status

Operating

Headcount range

11–50 employees

Short description

Thimble is a digital insurance platform serving micro-SMBs, freelancers, contractors, and gig workers with on-demand general liability, professional liability, property, and equipment coverage sold by the hour, day, month, or year via web and mobile, backed by A-rated carriers and operating as a subsidiary of Arch Insurance.

Ownership category

akta.pro rank

Product category

Small Business Insurance

NAICS

Agencies, Brokerages, and Other Insurance Related Activities (5242), Insurance Agencies and Brokerages (524210)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Workers’ Compensation for Small Business & Pay-As-You-Go Programs (FSAJAEAG)

akta.pro secondary industry

Product Liability (FSAJADAC)

Keywords

• Small business insurance
• On-demand insurance
• General liability insurance
• Professional liability insurance
• Gig economy insurance

Headquarters

HQ city

New York

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Technology or R&D, Marketing or Sales, Operations, Supply Chain

Revenue model

1. Insurance Premium Revenue: Thimble earns revenue by collecting insurance premiums from customers purchasing general liability, professional liability, business equipment protection, and other insurance products. Pricing varies by policy length (hour, day, month, year), coverage limits, industry, and risk profile. Customers pay upfront for their chosen coverage period.

Pricing tiers

Go-to-market motion3 records

Distribution channels5 records

Marketing channels6 records

Core offering

Thimble sells on-demand, flexible-duration small business insurance — including general liability, professional liability (E&O), business owners policy, commercial property, workers' compensation, business equipment protection, cyber, commercial auto, inland marine, event insurance, and surety bonds — through a digital platform that lets customers quote, bind, and download a Certificate of Insurance in minutes. Policies can be purchased by the hour, day, month, or year and are targeted at freelancers, contractors, gig workers, and small businesses across 1,000+ professions.

Product overview

Thimble is a digital small business insurance platform offering on-demand, pay-per-use coverage through a unified product. The core platform enables businesses to purchase general liability, professional liability, and commercial property insurance by the hour, day, month, or year with instant Certificate of Insurance generation. Core products include General Liability Insurance, Professional Liability Insurance, Business Owners Policy (BOP), Commercial Property Insurance, Workers' Compensation Insurance, and Business Equipment Protection. Add-on modules include Cyber Insurance, Commercial Auto Insurance, Inland Marine Insurance, Event Insurance, Surety Bonds, Customer Property Protection, and Hired & Non-Owned Auto Liability. The platform serves over 1,000 types of business activities across industries including contractors, photographers, DJs, musicians, landscapers, cleaning services, beauty professionals, event planners, and retailers. Platform tools include the Thimble mobile app for policy management and the Thimble Certificate Manager for broker operations. Industry-specific products include DJ & Musician Liability Insurance, Auto Detailing Insurance, Pressure Washing Insurance, and Retail Store Insurance.

Differentiator

Problem solved

Functional benefit

Products and services

• General Liability Insurance Protects small businesses against third-party claims of bodily injury, property damage, and personal/advertising injury. Core coverage offering for most small business insurance needs, available by the hour, day, month, or year.
• Professional Liability Insurance Errors & Omissions (E&O) insurance that protects against client claims that work was unsatisfactory, late, or never completed. Designed for consultants, freelancers, and service professionals.
• Business Owners Policy (BOP) Bundles general liability insurance and commercial property insurance (plus additional coverages) into one policy, providing comprehensive small business coverage.
• Commercial Property Insurance Covers business property and items on premises from accidental loss, damage, or theft. Designed for small businesses that own an office or retail store.
• Workers' Compensation Insurance Protects business owners and employees in the event an employee is injured or becomes ill as a result of their work.
• Business Equipment Protection Also known as inland marine insurance. Covers equipment used for business operations — from cameras to power tools — whether owned, rented, or borrowed.
• Cyber Insurance Protects small businesses against data breaches and cyber incidents. Particularly useful for mobile businesses taking bookings and payments digitally.
• Commercial Auto Insurance Coverage for business vehicles used in operations. Available in select states as an add-on to other Thimble policies.
• Event Insurance Short-term liability coverage for specific events, up to 5 days with setup/takedown included. Designed for weddings, festivals, and private gigs.
• Surety Bonds Surety bond products available through Thimble's platform for businesses requiring bond coverage as part of licensing, contractual, or regulatory requirements.
• DJ & Musician Liability Insurance Specialized general liability coverage package for DJs, musicians, and bands, including options for hourly, daily, monthly, or annual coverage with instant COI generation.
• Auto Detailing Insurance General liability coverage for auto detailing businesses and carwashes, protecting against third-party bodily injury and property damage claims.
• Pressure Washing Insurance Business insurance package for pressure washing and power washing contractors, including general liability and customer property protection options.
• Retail Store Insurance Specialized Business Owners Policy combining general liability and commercial property insurance for retail storefronts. Policy limits start at $300,000 for general liability, $250,000 for building coverage, and $50,000 for business contents.

Quantifiable outcome

• Get a quote and purchase coverage in minutes
• +2 more outcomes

Named customers7 records

Segments8 records

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature4 records

Partnerships

Five partnerships are on record, tiered core and minor.

• Markel Insurance CompanycoreTechnology or IntegrationMarkel Insurance Company (NYSE: MKL), a Fortune 500 company, underwrites insurance policies for Thimble. Rated 'A' (Excellent) by AM Best for financial strength and 'A+' for long-term issuer credit. One of Thimble's primary insurance carrier partners.
• National Specialty Insurance Company (NSIC)coreTechnology or IntegrationNational Specialty Insurance Company, a subsidiary of State National Insurance Company, underwrites Thimble policies. Rated 'A' (Excellent) by AM Best for financial strength and 'A+' for long-term issuer credit.
• Employers Insurance GroupcoreTechnology or IntegrationEmployers Insurance Group is one of Thimble's insurance carrier partners. Rated A- (Excellent) by AM Best for financial strength with a financial size category of XII ($1 billion to $1.25 billion).
• Impact RadiusminorGTM or Marketing PartnerImpact Radius is Thimble's affiliate program platform partner. Affiliates sign up through Impact Radius to earn commissions for referring customers to Thimble.
• AngicoreGTM or Marketing PartnerThimble is 'The Official Insurance of Angi' (formerly Angie's List). This partnership provides Thimble visibility with Angi's large network of homeowners and service professionals seeking contractors.

Scale indicators12 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• Next Insurance: Next Insurance is the leading digital SMB insurance carrier offering general liability, professional liability, and workers' comp directly online. It targets the same small contractor, freelancer, and gig worker segments as Thimble with a similar self-serve digital model, but operates as a direct carrier rather than an agency.
• Pie Insurance: Pie Insurance is a digital insurtech specializing in workers' compensation for small businesses, with expanding general liability offerings. It directly competes with Thimble in the digitally-distributed small business insurance market, and Ian Westerman (Thimble's current President) previously served at Pie.
• Hiscox: Hiscox is a specialty insurer with deep SMB and professional liability expertise, offering digital quote-bind experiences for small business customers. It serves the same freelance, consultant, and small business segments as Thimble, though through a carrier-owned model with a longer market tenure.
• CoverWallet: CoverWallet is a digital commercial insurance agency (acquired by Aon) that helps small and mid-sized businesses compare and purchase commercial policies online. It serves a similar SMB customer base with a comparable digital-first brokerage model, often overlapping with Thimble on general liability and BOP offerings.
• Coterie Insurance: Coterie Insurance is an insurtech MGA enabling agents and small businesses to bind commercial insurance instantly via API and platform integrations. It competes with Thimble's broker-facing tools and embedded distribution strategy for the same digital-first small business buyer.
• Simply Business: Simply Business is a digital commercial insurance broker (owned by Travelers) that helps small businesses compare and purchase liability and BOP policies online. It directly parallels Thimble's SMB-focused digital brokerage model with overlapping general liability and contractor coverage offerings.

Emerging players

• Bold Penguin: Bold Penguin operates a commercial insurance marketplace that connects SMBs and agents with multiple carriers through a digital platform. It is comparable to Thimble's Certificate Manager and broker portal strategy, though it focuses on the quoting and placement workflow rather than direct small business self-service.
• Insurify: Insurify is a digital insurance comparison platform that helps consumers and small businesses shop for insurance policies from multiple carriers. It shares Thimble's digital-first, self-serve acquisition philosophy but focuses on auto/home rather than commercial lines.

Broad incumbents

• Lemonade: Lemonade is a publicly-traded digital insurer using AI-driven underwriting and mobile-first design. While focused on renters, homeowners, and pet insurance, its consumer-facing digital insurance model and small team ethos make it a comparable insurtech benchmark for Thimble's PLG approach.
• Progressive Commercial: Progressive's commercial division provides business auto, general liability, and BOP coverage to small businesses through both digital and agent channels. It competes with Thimble for small contractor and service business insurance, but as a much larger incumbent with broader product lines.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/ThimbleInsurance
• LinkedInlinkedin.com/company/thimble
• Instagraminstagram.com/thimble
• Xx.com/thimble

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds3 records

Investors9 records

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Thimble