Outmarket lands $34.5M Series B to automate insurance brokerages with AI

Insurance agencies still rely heavily on manual paperwork and human judgment to navigate the complex world of commercial policies—a massive inefficiency gap that Outmarket is now moving to bridge. The startup, founded by veteran technologist Vishal Sankhala in late 2023, has just raised $34.5 million in Series B funding to scale its AI-powered administrative automation tools across the brokerage industry.

The opportunity#

Insurance remains one of the least digitized industries at scale. Roughly 95% of policies are still sold through human agents operating largely manual workflows. Commercial insurance is particularly intricate, with over 250 distinct coverage types—ranging from general liability and workers' compensation to directors and officers coverage—each requiring custom applications and specialized documentation reviews. That process, while essential for matching businesses to appropriate policies, consumes enormous amounts of broker time and creates bottlenecks.

How Outmarket works#

The platform automates the paperwork and administrative grunt work that traditionally slows brokers down, allowing agency teams to focus on high-value customer interactions and emergency response rather than form-filling. Sankhala, who previously led product at life insurance distributor Ethos (which went public earlier this year) and held engineering roles at Facebook and Uber, positioned Outmarket as the operating system that helps brokers work smarter and faster.

Investor confidence#

The company has already attracted over 300 insurance agencies since launching its core product 14 months ago, including one-quarter of the top 100 brokerages in the U.S.—rapid adoption for an industry not known for quick change. SignalFire led the Series B round, with backing from Fika Ventures, Permanent Capital Ventures, TTV Capital, and Dash Fund. The funding values Outmarket at $355 million, just four months after closing a $17 million Series A.

The market ahead#

The U.S. property and casualty insurance sector alone represents over $1 trillion in annual premiums. Outmarket faces competition from startups like Fulcrum AI and Further AI, but the scale of the market leaves ample room for multiple winners focused on modernizing brokerage workflows.