Huckleberry business insurance

Overview

Huckleberry is an online insurance agency, not an insurance company. Since 2023 it has belonged to Paychex, Inc., the payroll and HR company based in Rochester, New York (Nasdaq: PAYX), and the site now trades as "Huckleberry by Paychex," which its FAQ describes as the digital quoting and binding tool of Paychex Insurance Agency, Inc. The agency is the licensed producer on the sale. The policy is issued by one of the carriers it places business with, and the carrier logos on huckleberry.com in October 2026 were AmTrust, Chubb, CopperPoint, EMPLOYERS, GUARD, The Hartford, Hiscox, Markel and Pie. Your declarations page, not the Huckleberry name, tells you which insurer is on the risk.

Huckleberry is paid the way most agencies are: a commission from the insurer, built into the premium you pay. The site says it never charges broker fees. Its legal disclosures add that Paychex Insurance Agency may also receive other compensation from insurers or intermediaries, which is standard wording for contingent and override arrangements; how commercial insurance brokers get paid explains how those work.

It sells online across the country. The FAQ says it can quote in every state and the District of Columbia, with individual coverages varying by state. Workers' comp, the product Huckleberry was built on, cannot be bought from any private agency in North Dakota, Ohio, Washington or Wyoming, where comp comes only from the state fund (see Monopolistic state funds: workers' comp in ND, OH, WA and WY); Paychex's SurePayroll page for the Huckleberry-powered comp product excludes exactly those four states.

History

Bryan O'Connell and Steve Au launched Huckleberry in San Francisco in 2017. According to TechCrunch's 2019 profile, the idea came from their own struggle to buy coverage for an earlier startup, and O'Connell had previously worked at an insurance carrier. The pitch was a workers' comp policy and a BOP-style package quoted in under five minutes from public and private data, with no paper application or phone tag with an agent.

In December 2019 Huckleberry raised an $18 million Series A led by Tribe Capital, with Crosslink Capital, Uncork Capital and Amaranthine participating, and said it would expand into personal care, auto repair and restaurants. Total disclosed funding reached about $22 million. The trade site Coverager later reported that the company had struggled with profitability and with raising new capital, and had cut its staff by nearly half over two years.

Paychex took over the business in 2023. Neither company issued a press release; Coverager noticed in late summer 2023 that the site had switched from Huckleberry's purple to Paychex blue with the Paychex name, and investor Promus Ventures lists Huckleberry as acquired by Paychex in 2023. Since then the copyright, licenses and address on huckleberry.com are those of Paychex Insurance Agency, and Paychex's SurePayroll unit sells a workers' comp product, SureProtect, described as powered by Huckleberry and Paychex.

Paychex itself was founded in 1971 by B. Thomas Golisano. It reports about 840,000 customers and dual headquarters in Rochester and Cincinnati, and John B. Gibson has been president and CEO since 2022.

Business insurance products

Huckleberry quotes five core lines online:

• Workers' compensation, the original product. Premium is a rate per $100 of payroll by class code, and an end-of-term premium audit trues it up to actual payroll. The FAQ says you can include 1099 contractors who have no comp of their own in the quote; if they are insured elsewhere, the carrier may ask for proof (see independent contractors and workers' comp: the misclassification risk).
• Business owner's policy: general liability, building and business personal property, and business income in one package (see What is a business owner's policy (BOP)?).
• General liability as a standalone policy, for businesses with no property to insure.
• Cyber liability. The FAQ says most customers buy the Paychex Cyber Liability Basic program, quoted online with a $250,000 aggregate limit; higher limits need a conversation with an agent through chat.
• Commercial auto.

Optional coverages offered with the package include business property, business interruption, professional liability, hired and non-owned auto, liquor liability, employment practices liability, spoilage, equipment breakdown, a restaurant endorsement and employee dishonesty. Huckleberry does not list surety bonds, umbrella or inland marine. Paychex Insurance Agency's broader book, sold by its licensed agents, adds commercial property, commercial umbrella and errors and omissions.

Who it insures

Huckleberry targets very small employers in main-street classes. Its professions page lists DJs and photographers; auto detailers, auto repair shops and car dealerships; commercial and residential cleaners, carpet cleaners, dry cleaners and laundromats; appliance technicians, carpenters, electricians, HVAC businesses, painters, plumbers, pressure washers and flooring installers; accountants and financial planners; bakeries, caterers, coffee shops, food trucks, Restaurant insurance and bars, and wineries; medical offices, massage therapists and physical therapists; landscapers; barbers, hairstylists, nail technicians and spas; engineers and law firms; nonprofits; property managers and real estate agents; retail stores; daycare centers, dog groomers, event planners and tutors; and fitness, yoga, Pilates, dance and martial arts studios.

Whether your class is quotable depends on each carrier's appetite on the day you apply. The FAQ says carriers sometimes refer an application for a closer look, usually answered the same business day, and that a lapse in workers' comp coverage does not mean an automatic decline but may trigger requests for documents. Contractors who need performance bonds, fleets, hazardous classes and accounts that need surplus lines markets are outside what an online panel like this handles; an independent agent with wholesale access is the better route for those.

How to buy

You buy at huckleberry.com. You answer the questions, see quotes from more than one carrier side by side, pick one, sign electronically and pay. No credit card is needed to see a price. You can set a start date up to 90 days out, and the first month's premium is charged on the day you buy. Support runs through live chat, the support email and the phone line.

Paychex payroll clients have a second route: Paychex's licensed agents quote several carriers by phone, can tie premium payments to payroll (the logic behind pay-as-you-go workers' comp: how it works and who it suits), and on certain plans re-shop the policy about 90 days before renewal.

Certificates of insurance are self-service at huckleberry.com/certificate. You can issue unlimited copies, add certificate holders and additional insured parties, and request common endorsements there. Remember that a certificate of insurance is evidence of coverage, not coverage; an additional insured endorsement has to be on the policy itself.

Because Paychex Insurance Agency is your agent of record, mid-term changes go through Huckleberry rather than the carrier. If you later move the account to another agent, expect to sign a broker-of-record letter.

Claims

Huckleberry does not decide or pay claims; the carrier does, and the FAQ says so plainly. Report a claim using the instructions in your policy documents, or call Huckleberry at 855-255-4825 for help reaching the right carrier. For a workplace injury, the site's advice is the correct order of operations: get the employee medical care first, then report. Prompt reporting matters in comp, where a late first report can raise claim costs and complicate the carrier's investigation (see reporting a workplace injury: what employers must do).

Claim service, nurse triage and adjuster quality are the issuing carrier's, so read that carrier's profile for its claims lines and practices.

Financial strength and ratings

Agencies carry no AM Best, S&P, Moody's or Fitch financial strength rating, and Huckleberry has none. The rating that matters is the one on the insurer named on your declarations page. Huckleberry describes its partners as A-rated carriers, but its panel spans several companies with different ratings, so check the specific issuing company (see AM Best ratings explained for business buyers). J.D. Power's U.S. Small Commercial Insurance Study ranks insurers, not agencies, and Huckleberry does not appear in it.

The agency's own finances affect service, not claim payment. Before 2023 Huckleberry was a venture-funded startup that Coverager reported was losing money and shrinking; it now sits inside Paychex, a public company with about 840,000 customers. Neither Paychex nor Huckleberry has published financial results for the Huckleberry business.

Strengths and weaknesses

Huckleberry is a fast way for a very small employer to buy a monoline comp policy or a BOP online, with several brand-name carriers quoting at once. Its limits are those of any online agency: the menu is narrow, the advice is light, and since the Paychex takeover the brand's long-term role inside Paychex's insurance agency has not been spelled out publicly.

• Strengths: Side-by-side online quotes from carriers including AmTrust, Chubb, EMPLOYERS, GUARD, The Hartford, Hiscox and Markel; no broker fees; unlimited self-service certificates with additional insured requests; Paychex ownership and an optional payroll-linked route through Paychex's agents.
• Weaknesses: An agency, so claims, ratings and coverage forms depend on whichever carrier you end up with; no bonds, umbrella or surplus lines access listed; cyber online is mainly a $250,000 aggregate program; no workers' comp in the four monopolistic state-fund states; a quiet 2023 acquisition with no public announcement of plans for the brand.

How to contact Huckleberry