Huckleberry
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.
- Company typePrivate
- Founded2017
- HeadquartersSan Francisco, United States
- Headcount11–50
- GTM typeB2C
- OfferingServices
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.
Huckleberry firmographics
Firmographics- 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
Huckleberry industry classification
Industry- 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
Where Huckleberry is headquartered
LocationHeadquarters
- HQ city
- San Francisco
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Huckleberry business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Technology or R&D, Personnel, Marketing or Sales, Operations
Revenue model
- 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.
- 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
| Model | Billing | Price |
|---|---|---|
| Subscription | Monthly | Workers' Compensation Insurance - Median premium $1,123/year, as low as $271/year |
| Subscription | Monthly | Business Owner's Policy (BOP) - Median premium $750/year (~$2/day) |
| Subscription | Monthly | General Liability Insurance - Median premium $700/year, as low as $34/month |
| Subscription | Monthly | Cyber Liability Coverage - Starting at $500/year ($41.67/month) |
| Other | Monthly | No website usage fees - commission-based model |
Go-to-market motion2 records
Distribution channels3 records
Marketing channels4 records
Huckleberry product offering
Product offeringCore 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
Companies that use Huckleberry
Customer profileNamed customers10 records
Segments15 records
Ideal customer profiles1 record
Huckleberry technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
AI capability2 records
Feature3 records
Huckleberry partnerships and signals
Strategic signalScale indicators3 records
Recent moves6 records
Expansion highlights5 records
Huckleberry competitors and assessment
Company assessmentDirect 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
Huckleberry social profiles
Digital presenceHuckleberry financial estimates
Financial estimateRevenue estimate
Valuation estimate
Huckleberry leadership team
Management profileNumber of profiles
Profiles3 records
Huckleberry funding detail
Funding detailFunding overview
Funding rounds5 records
Investors13 records
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Huckleberry M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Huckleberry
What does Huckleberry do?
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.
Is Huckleberry a public or private company?
Huckleberry is a private company. It is classified as corporate owned and is currently operating.
When was Huckleberry founded?
Huckleberry was founded in 2017. It employs 11 to 50 people.
Where is Huckleberry based?
Huckleberry is headquartered in San Francisco, United States, in the North America region.
How does Huckleberry make money?
Two revenue lines are on record. Insurance Agency Commissions are the primary driver. The others are insurance Premiums (as agent).
Who are Huckleberry's main competitors?
Direct peers on record are Pie Insurance, Next Insurance, CoverWallet, Thimble and Simply Business. Broad incumbents are Hiscox and The Hartford. Emerging players are Insurify and Bold Penguin. Paychex (PEO/SMB Services arm) is listed as an others.
Does Huckleberry have an API?
No public API is recorded for Huckleberry.
What industry is Huckleberry in?
Huckleberry's product category is Small Business Insurance. Its primary akta.pro industry code is FSAJAFAA, Small Business BOP (Main Street), with a secondary code of FSAJAEAG, Workers’ Compensation for Small Business & Pay-As-You-Go Programs. Its NAICS code is 52421 and its SIC code is 6411.