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

Dakotah Rice is making a significant return to entrepreneurship, unveiling his latest venture, Harper, an AI-powered insurance brokerage. On Wednesday, Rice announced that Harper has successfully raised approximately $46.8 million in a combination of Series A and seed funding. Previously, Rice founded Poolit, an investment company that closed its doors in 2023. Reflecting on that experience, he candidly shared with TechCrunch that he struggled to find a path to profitability and regretted not shutting down the business sooner. Drawing inspiration from his family's background in insurance, Rice initially harbored a disdain for the industry, vowing never to return. However, a new idea emerged. Alongside Tushar Nair, a longtime friend and former CTO of Poolit, they initially considered developing AI tools for traditional brokerages. Ultimately, they pivoted to creating an AI-native brokerage, naming it Harper in honor of Rice’s mother’s maiden name. Launched in 2024, Harper embodies a growing trend highlighted by Y Combinator, which noted that future agencies will increasingly resemble software companies with software-like profit margins. Harper operates as a nearly autonomous, licensed commercial insurance agency, connecting small to mid-sized businesses with over 160 insurance carriers for services such as workers' compensation and liability insurance. According to Rice, while traditional brokers may take five to seven days to process applications, Harper can achieve this in just one to two days. The efficiency of AI allows Harper to serve more than 1,000 clients monthly, compared to the typical 20 to 30 deals managed by a human-led team. With over 5,000 customers already, the company is making significant strides. The operational burdens—such as submission routing, underwriter follow-ups, document collection, and pipeline management—are all efficiently handled by AI. Notable investors include Y Combinator and Peak XV Partners, with Emergence Capital leading the seed and Series A rounds. In less than two months, Harper has successfully amassed $54 million in funding. Rice views virtually all brokerages as competitors, noting the industry's fragmentation where major players and smaller firms still rely on outdated tools like email and spreadsheets. While other AI-driven brokerages exist, such as Gyde and alumni like FurtherAI and Vantel, Rice emphasizes Harper's mission to focus on middle America, aiming to serve 'real-world businesses' such as daycares, manufacturers, and local restaurants. The recent funding will bolster Harper’s engineering team and brand growth. With renewed ambition, Rice envisions Harper as a comprehensive resource for entrepreneurs, initially addressing their insurance needs and expanding to encompass various aspects of risk management, compliance, and operational support, ultimately simplifying their core business functions.