Harper, an AI-native commercial insurance brokerage founded by Dakotah Rice, has raised $46.8 million across a combined Seed and Series A round.
The company participated in Y Combinator’s W25 batch. The Series A was led by Emergence Capital, with backing from Y Combinator, Peak XV Partners, and other investors.
From Founder Failure To AI-First Brokerage
Dakotah Rice previously founded investment platform Poolit, which shut down in 2023 after struggling to reach profitability. Reflecting on that experience, Rice has said he learned difficult lessons about timing and sustainability.
For his next venture, he returned to a familiar industry. Rice grew up around insurance, as his family owned an insurance brokerage. Although he once resisted entering the sector, he recognized inefficiencies in how businesses, especially founders, secure coverage.
Together with Tushar Nair, former CTO of Poolit, Rice initially explored building AI tools for traditional brokerages. The pair ultimately decided to launch a fully AI-native brokerage instead, naming it Harper after Rice’s mother’s maiden name.
Advertisement
Automating The Brokerage Model
Founded in 2024, the company operates as a licensed commercial insurance agency serving small- and mid-sized businesses. The platform matches companies with more than 160 insurance carriers, covering policies such as workers’ compensation, general liability, and professional liability.
Unlike traditional brokerages that rely heavily on manual processes, Harper uses AI to automate submission routing, underwriter follow-ups, document collection, and pipeline management.
According to Rice, processes that typically take five to seven days through conventional brokers can often be completed within one to two days on Harper’s platform. While traditional sales teams may handle a few dozen deals per month, Harper’s AI-driven system allows it to serve more than 1,000 customers monthly. The company reports more than 5,000 customers to date.
The model aligns with a broader trend identified by Y Combinator, where agencies increasingly resemble software companies in structure and margins, driven by automation and scalable technology.
Targeting Main Street Businesses
Rice views most traditional brokerages as competitors, describing the industry as fragmented and still reliant on email and spreadsheets. While other AI-enabled brokerages and insurance automation startups are emerging, Harper aims to differentiate itself by focusing on everyday businesses across middle America.
The company targets sectors such as daycare centers, manufacturers, car dealerships, restaurants, and other local operators seeking efficient access to commercial insurance.
Expanding The Platform
The newly raised capital will be used to expand Harper’s engineering team and strengthen brand awareness. Over time, Rice envisions Harper becoming more than an insurance brokerage.
The long-term ambition is to build a broader operational layer for entrepreneurs, supporting risk management, compliance, and back-office workflows beyond insurance.
About Harper
Harper is an AI-native commercial insurance brokerage founded in 2024. The platform automates insurance placement for small- and mid-sized businesses, leveraging artificial intelligence to streamline underwriting workflows, carrier matching, and policy management. By combining licensed brokerage services with AI automation, Harper aims to modernize commercial insurance for entrepreneurs and growing companies.
