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

TechCrunch

by Dominic-Madori Davis

February 25, 2026

AI-Generated Deep Dive Summary

Dakotah Rice, founder of failed investment firm Poolit, has made a comeback with Harper, an AI-native insurance brokerage that recently raised $46.8 million in a combined Series A and seed round. This new venture aims to revolutionize the insurance industry by leveraging artificial intelligence to streamline processes traditionally handled by human brokers. Inspired by his family’s background in insurance, Rice identified inefficiencies in the system, particularly for small- to mid-sized businesses seeking coverage like workers’ compensation or general liability. Harper’s AI-driven approach allows it to handle over 1,000 customers monthly, compared to just 20-30 deals processed by traditional brokers. This efficiency highlights the potential of AI to transform the insurance sector. Launched in 2024 and part of Y Combinator’s W25 cohort, Harper operates as a fully autonomous licensed commercial insurance agency. It connects businesses with over 160 carriers, automating tasks such as submission routing, underwriter follow-ups, and document collection. This automation not only accelerates the process—often reducing timelines from five to seven days down to just one or two—but also significantly scales operations. With over 5,000 customers to date, Harper is positioning itself as a disruptor in an industry still reliant on manual processes and fragmented tools like email and spreadsheets. While competitors like Gyde, FurtherAI, and Vantel also use AI, Harper distinguishes itself by targeting middle America’s real-world businesses, such as daycares, manufacturers, car dealerships, and local restaurants. This focus on underserved markets aligns with Rice’s vision to become a comprehensive solution for entrepreneurs’ risk management needs, eventually expanding into areas like compliance and back office operations. The fresh funding will be used to expand Harper’s engineering team and build its brand presence. Rice’s journey reflects the growing trend of AI-driven innovation in traditionally slow-moving industries. By reimagining insurance as a software company with high margins, Harper not only addresses inefficiencies but also sets a higher bar for customer expectations. This shift matters to tech enthusiasts and investors alike, as it underscores the broader potential of AI to disrupt industries that have long lagged behind technological advancements. Harper’s success could pave the way for similar innovations in other sectors, making complex processes simpler and more accessible for everyday businesses.

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Originally published on TechCrunch on 2/25/2026