Huckleberry

What Huckleberry does

Huckleberry is a digital small business insurance agency that enables business owners to purchase insurance policies entirely online in under five minutes through a paperless, self-serve platform. Operated by Paychex Insurance Agency, Inc. (a subsidiary of Paychex, Inc., NASDAQ: PAYX), the platform sells directly to SMBs across all 50 US states and offers a core portfolio of Workers' Compensation Insurance and Business Owner's Policy (BOP), complemented by more than a dozen add-on coverages including General Liability, Cyber Liability, Commercial Auto, Professional Liability (E&O), Employment Practices Liability (EPLI), Liquor Liability, Business Interruption, Property, Spoilage, Equipment Breakdown, and Employee Dishonesty coverage.

The platform is built around an instant quote engine, a 100% digital application process with electronic signatures, and AI-powered features such as chatbots and conversational NLP assistants for customer support and automated underwriting. Policies are underwritten by a panel of nine A-rated carrier partners (Amtrust, Berkshire Hathaway Guard, Chubb, The Hartford, Markel, Hiscox, Pie, Copperpoint, and Employers), enabling multi-carrier comparisons within a single 5-minute flow. The company targets 15+ SMB verticals including restaurants, commercial cleaners, plumbers, landscapers, carpenters, medical practices, and daycare centers.

Huckleberry generates revenue through commissions from insurance carriers on policies sold through its platform, with no fees charged to customers for using the website. Median policy pricing ranges from approximately $700/year for General Liability to $1,123/year for Workers' Compensation, billed monthly. The business is headquartered in Rochester, NY, and operates as a brand within Paychex's insurance agency operations, leveraging Paychex's small business customer base, brand recognition, and operational infrastructure.

Name

Huckleberry

Legal name

Paychex Insurance Agency, Inc.

Website

https://huckleberry.com

Company type

Private

Founded year

2017

Operating status

Operating

Headcount range

11–50 employees

Short description

Huckleberry is a digital insurance agency operated by Paychex Insurance Agency, Inc. that sells small business insurance online in under five minutes. It serves SMBs across 15+ US industries with Workers' Comp, BOP, and 13+ add-on coverages from A-rated carriers.

Ownership category

akta.pro rank

Product category

Small Business Insurance

NAICS

Insurance Agencies and Brokerages (52421)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Small Business BOP (Main Street) (FSAJAFAA)

akta.pro secondary industries

Workers’ Compensation for Small Business & Pay-As-You-Go Programs (FSAJAEAG), Restaurants, Bars & Food Service BOP (FSAJAFAG), Contractors BOP / Artisan Package (FSAJAFAD)

Keywords

• Small business insurance
• Workers compensation insurance
• Business owners policy
• General liability insurance
• Cyber liability coverage

Headquarters

HQ city

San Francisco

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Insurance Agency Commissions: Acts as an insurance agent representing multiple insurance carriers. Receives commissions and/or additional compensation from insurance companies or intermediaries in connection with the sale of insurance products to customers.
2. Insurance Premiums (as agent): Facilitates the sale of insurance policies. While coverage decisions, premiums, commissions and fees are determined by the underwriting insurance company, Huckleberry processes and manages the policy through their platform.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels4 records

Core offering

Huckleberry is an online insurance agency that sells small business insurance policies directly to business owners through a digital, paperless platform. The company acts as an agent representing multiple A-rated insurance carriers, offering workers' compensation, business owner's policy (BOP), general liability, cyber liability, commercial auto, business property, business interruption, and professional liability coverage. Customers complete an online questionnaire, receive instant quotes, sign electronically, and purchase coverage in under five minutes without phone calls or paperwork.

Product overview

Huckleberry is an online small business insurance agency operated by Paychex Insurance Agency, Inc. that enables businesses to purchase insurance entirely online in under 5 minutes without paperwork. The platform offers a core portfolio of Workers' Compensation Insurance and Business Owner's Policy (BOP), alongside standalone add-on coverages including General Liability, Cyber Liability, Commercial Auto, Business Property, Business Interruption, Professional Liability (E&O), Hired and Non-Owned Auto, Liquor Liability, Employment Practices Liability (EPLI), Spoilage Coverage, Equipment Breakdown, Restaurant Endorsement, and Employee Dishonesty Coverage. The BOP bundles general liability, property, and business interruption into a single package. All policies are underwritten by carrier partners including Amtrust, Berkshire Hathaway Guard, Chubb, The Hartford, Markel, Hiscox, Pie, and Copperpoint.

Differentiator

Problem solved

Functional benefit

Products and services

• Workers' Compensation Insurance

Quantifiable outcome

• 95% of customers complete coverage process in 5 minutes
• +5 more outcomes

Named customers10 records

Segments15 records

Ideal customer profiles1 record

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

AI capability2 records

Feature3 records

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Pie Insurance: Digital workers' compensation provider targeting small businesses; also a Huckleberry carrier partner. Directly comparable in product (workers' comp for SMBs) and digital GTM, and competes for the same small business search/SEO traffic.
• Next Insurance: Digital SMB insurance agency offering workers' comp, general liability, BOP and commercial auto to small businesses online. Closest direct competitor — same product set, same self-serve digital GTM, same vertical segmentation strategy.
• CoverWallet: Digital commercial insurance platform serving small and mid-sized businesses with multiple commercial lines via a self-serve online experience. Directly comparable in target customer (SMB) and digital distribution model.
• Thimble: On-demand small business insurance offering general liability and professional liability by the day, month or year through a digital platform. Comparable in digital-first SMB focus and self-serve UX.
• Simply Business: Online commercial insurance marketplace and broker for small businesses, comparing quotes across multiple carriers. Comparable in aggregating SMB commercial insurance demand digitally across multiple carrier partners.

Broad incumbents

• Hiscox: Global specialty insurer with a dedicated small business digital channel and active direct-to-SMB distribution. Comparable as both a Huckleberry carrier partner and a broader incumbent that competes for the same digital SMB customers.
• The Hartford: Major U.S. commercial lines carrier with a strong small business franchise (especially workers' comp). Comparable as a Huckleberry carrier partner and a broad incumbent competing in the same SMB commercial insurance category.

Emerging players

• Insurify: Insurance comparison platform with growing SMB commercial lines offerings. Comparable as a digital insurance acquisition channel competing for SMB insurance search demand.
• Bold Penguin: Commercial insurance marketplace connecting small businesses and agents with multiple carriers. Comparable in enabling SMB commercial insurance distribution through a digital platform; competes for the same broker/carrier ecosystem.

Others

• Paychex (PEO/SMB Services arm): Huckleberry's parent company; while not an external peer, Paychex's PEO and benefits advisory business represents an internal adjacency through which Huckleberry insurance products are cross-sold — a unique structural relationship versus any other peer.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/huckprotects
• Facebookfacebook.com/huckprotects

Revenue estimate

Valuation estimate

Number of profiles

Profiles3 records

Funding overview

Funding rounds5 records

Investors13 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 Huckleberry