Harper, an AI-powered insurance brokerage that graduated from Y Combinator's Winter 2025 cohort, just closed a $47 million combined seed and Series A round. The deal signals renewed investor appetite for AI applications tackling antiquated industries, with insurance emerging as a prime target for automation. Harper's rapid progression from YC demo day to multimillion-dollar raise underscores how quickly AI-native startups can scale when they target high-friction markets ripe for disruption.
Harper is making a big bet that artificial intelligence can fix one of the most frustratingly manual corners of finance. The startup, which just emerged from Y Combinator's Winter 2025 batch, closed $47 million in back-to-back seed and Series A funding according to TechCrunch.
The deal stands out not just for its size but for its speed. Harper compressed what typically takes startups 18 to 24 months into a matter of weeks, moving from YC demo day to a substantial Series A without the usual multi-year grind. That acceleration tells you everything about where venture capital is flowing right now: toward AI startups attacking legacy industries with demonstrable unit economics.
Insurance brokerage remains shockingly manual. Brokers still juggle spreadsheets, email chains, and phone calls to match clients with policies. The process can take weeks, involves mountains of paperwork, and leaves both brokers and customers frustrated. Harper's pitch is straightforward - use AI to automate the repetitive work, speed up policy placement, and let human brokers focus on complex cases and relationship management.
The insurance industry has flirted with technology for years, but AI is finally delivering on automation promises that earlier software couldn't fulfill. Large language models can parse policy documents, extract relevant coverage details, and match client needs with carrier options faster than human brokers. The difference between Harper and previous insurtech waves is that the technology has caught up to the ambition.
Y Combinator has been doubling down on AI-native companies over the past year. The accelerator's Winter 2025 cohort featured the highest concentration of AI startups in its history, with nearly 40% of accepted companies building on foundation models. Harper fit the pattern perfectly: experienced founders, clear market pain point, and AI as the core product rather than a feature bolted onto existing software.
