Huckleberry raises $18 million to match small businesses with insurance plans using AI

Small businesses are generally unprepared for unforeseen catastrophes, surveys show. A whopping three-fourths of U.S.-based outfits say they don't have an insurance policy that meets their unique needs, while 40% admit they don't have coverage of any kind. Of course, the latter are on the hook for incidents like client complaints, contract disputes, and employee injuries, in addition to burglary or theft and customer injury -- all of which can amount to hundreds of millions of dollars in repairs and remedial disbursements. That's why in 2017 former McKinsey business analyst and Morgan Stanley associate Bryan O'Connell founded Huckleberry, a carrier built on a robust cloud-based software and data science and analytics backend. The San Francisco-based company ambitiously aims to digitize the purchase and management of commercial insurance, a category of coverage that's notoriously slow to acquire and which historically has been wrapped up in layers of bureaucracy.