Y Combinator grad and AI insurance brokerage Harper raises $47M

Source: TechCrunch

Announcement

Dakotah Rice is stepping back into the founder’s seat. On Wednesday, he announced that his new company, the AI‑native insurance brokerage Harper, has raised $46.8 M in a combined Series A and seed round.

Background

Rice previously founded the investment company Poolit, which closed in 2023. He spoke openly to TechCrunch about the collapse, saying he never figured out how to make it profitable:

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

For his next venture, Rice returned to his roots. His family owned an insurance brokerage, and he remembered the hassles founders faced when trying to insure their businesses. “I hated insurance,” he said, “swore I’d never end up in it.”

The Idea Behind Harper

Together with longtime friend and former Poolit CTO Tushar Nair, Rice initially considered building AI tools for existing brokerages. They soon decided to use that technology to create an AI‑native insurance brokerage, naming it Harper after Rice’s mother’s maiden name.

Harper launched in 2024 as part of the YC W’25 batch. Y Combinator noted that the future of agencies “will look more like software companies, with software margins.” Harper is an almost fully autonomous licensed commercial insurance agency that matches small‑ to mid‑sized businesses with more than 160 insurance carriers for 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,” said Rice, the company’s CEO.
“A typical sales team at a human‑led brokerage handles 20–30 deals a month, but AI enables Harper to handle more than 1,000 customers a month.”
Harper has more than 5,000 customers to date.

How AI Powers Harper

AI handles the operational weight: submission routing, underwriter follow‑ups, document collection, and pipeline management.

Funding

Investors include Y Combinator, Peak XV Partners, and the seed and Series A rounds were led by Emergence Capital. Rice said Harper has raised $54 M in funding to date, achieving that amount in just under two months.

Competition and Differentiation

Rice views nearly all traditional brokerages as competition, noting the market remains fragmented with many players still operating on “email and spreadsheets.” Other AI‑native brokerages in the space include Gyde, as well as companies that use AI tools such as FurtherAI and Vantel (both YC alums).

What sets Harper apart is its focus on “middle America”—real‑world businesses like daycares, manufacturers, car dealerships, local bars, and restaurants.

Future Plans

The fresh funding will be used to expand Harper’s engineering team and grow the brand. Rice’s vision:

“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. We want to make it simple for them to do their core work, and we basically do everything else over time.”