Harper, an AI-driven insurance brokerage that emerged from Y Combinator, secures $47 million in funding to revolutionize the insurance tech landscape.

With a fresh injection of $47 million in capital, Dakotah Rice's Harper is poised to revolutionize the traditional insurance brokerage landscape, employing AI to streamline time-intensive tasks and manage over 1,000 clients monthly, far outstripping the capabilities of conventional brokers. This Y Combinator-backed venture not only promises enhanced efficiency but also aims to improve service quality, transforming insurance into a seamless aspect of business operations.

Chris Wilson

February 25, 2026

Dakotah Rice, a founder who candidly admitted to the stumbling of his previous venture, is making a calculated return with Harper, an AI-driven insurance brokerage. With a recent $47 million boost in funding, Harper is not just launching another tech firm; it's aiming to transform how we view insurance operations traditionally dominated by human brokers. According to TechCrunch, this Y Combinator-backed initiative is leveraging AI to substantially cut down the time required for insurance processes, setting a new efficiency standard in the industry.

At its core, Harper employs AI to automate mundane and time-consuming tasks like submission routing and document collection, which traditionally take days, if not weeks. This technology-driven approach enables Harper to manage over 1,000 customers monthly - a number that dwarfs the capabilities of many traditional insurance brokerages. Furthermore, Harper's AI system isn't just about quantity; it's designed to enhance the quality of service, making insurance less of a hassle and more of a seamless part of business operations.

Rice's strategy is to innovate from within by drawing on his personal disdain for the traditional insurance model - a sentiment that sparked the inception of Harper. This is more than an entrepreneurial pivot; it's a disruption aimed at the insurance brokerage sector, which still largely operates on an outdated model of "email and spreadsheets." The irony here is palpable - Rice swore off insurance only to return with a vengeance, equipped with AI tools. This not only exemplifies a perfect circle in his career but also highlights the transformative potential of AI in sectors traditionally resistant to change.

It's not just about replacing a broker with a bot. Harper is strategically targeting "real-world" businesses - the daycares, manufacturers, and local restaurants that form the backbone of middle America. This focus potently combines innovative technology with market segments that are often overlooked by larger, more traditional firms, suggesting a targeted approach to both service quality and market penetration.

With Harper, Rice is not just rewriting his entrepreneurial story; he's drafting a new narrative for the insurance industry. If the past failures were stepping stones, the massive funding and innovative model might just be the recipe for his and many small businesses' success. Harper's journey from a reflective failure to a robust re-entry into the business world underscores a fundamental truth in fintech: innovation, when thoughtfully applied, can transform even the most stagnant of industries.

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