Y Combinator-backed AI insurance brokerage Harper secures $47M in funding

Dakotah Rice is returning to the founder role. On Wednesday, he announced that his new AI-native insurance brokerage, Harper, has raised $46.8 million in a combined seed and Series A round.

Rice previously founded the investment firm Poolit, which shut down in 2023. He has spoken candidly about that company’s collapse, saying he never figured out a path to profitability.

“My ego made it hard to accept the failure,” he said. “In hindsight, I should have shut it down a year earlier.”

For his next venture, Rice said he went back to what he knew. His family owned an insurance brokerage, and he remembered the frustration and complexity founders faced when trying to insure their businesses. “I hated insurance,” he said, adding that he “swore I’d never end up in it.”

But the experience eventually sparked an idea. Rice and Tushar Nair — a longtime friend and the former CTO of Poolit — originally considered building AI tools for existing insurance brokerages. They later decided to use that same technology to create an AI-native brokerage of their own. They named it Harper, after Rice’s mother’s maiden name.

Harper launched in 2024 and is part of a broader trend highlighted by Y Combinator. Harper participated in the YC W25 batch, and YC has argued that the future of agencies “will look more like software companies, with software margins.” Harper is built around that approach: it operates as an almost fully autonomous, licensed commercial insurance agency.

The company matches small- and mid-sized businesses with more than 160 insurance carriers, helping them obtain coverage such as workers’ compensation, general liability, and professional liability.

“What often takes a traditional broker five to seven days, we can often do in one to two,” Rice, Harper’s CEO, said. He added that a typical human-led brokerage sales team handles 20-30 deals per month, while Harper’s AI-driven setup supports more than 1,000 customers per month. Harper has served more than 5,000 customers so far, he said.

“AI handles the operational weight. Submission routing, underwriter follow-ups, document collection, pipeline management,” Rice said.

Harper’s investors include Y Combinator, Lobster Capital, and Peak XV Partners, and the Series A was led by Emergence Capital.

Rice said he sees nearly the entire brokerage industry as Harper’s competitive landscape, arguing that much of the market remains fragmented, with large firms on one end and a long tail of smaller brokerages still relying heavily on “email and spreadsheets.” Other AI-native brokerages are emerging, such as Gyde, along with companies that build AI tools for insurance workflows, including FurtherAI and Vantel, both YC alums.

Rice said Harper’s focus is on what he described as middle America — “the real-world businesses,” such as daycares, manufacturers, car dealerships, and local bars and restaurants.

The new funding will be used to expand Harper’s engineering team and help build the brand. Rice said he has big ambitions for the company in this second run as a founder.

“We want to become the voice for entrepreneurs, starting with their insurance, but over time becoming a focal point for all types of things related to risk, compliance, and their entire back office,” he said. “We want to make it simple for them to do their core work, and we basically do everything else over time.”