Y Combinator Grad And AI Insurance Brokerage Harper Raises $47M

AI Insurance Brokerage Harper Secures $47M

What if getting business insurance didn't mean endless forms, confusing quotes, and weeks of back-and-forth? An AI insurance brokerage called Harper is changing that equation. The startup, founded by serial entrepreneur Dakotah Rice, just closed a $47 million funding round to scale its autonomous platform. Harper matches small and mid-sized businesses with tailored commercial coverage in minutes, not months. Here's how this venture is reimagining insurance for the digital age—and why investors are betting big on its AI-native approach.

Credit: Google

From Startup Setback to AI Insurance Innovation

Dakotah Rice knows the weight of a founder's setback. His previous venture, an investment platform, closed in 2023 after he couldn't crack a profitable model. He's been open about that chapter, noting that ego sometimes delays hard decisions. But that experience became fuel. Rice returned to his roots: his family once ran a traditional insurance brokerage, and he remembered the friction founders faced when seeking coverage. "I hated insurance," he admits, "and swore I'd never end up in it." Yet that very frustration sparked the idea for Harper.
Instead of building incremental tools for existing brokerages, Rice and co-founder Tushar Nair asked a bolder question: What if the brokerage itself was rebuilt around artificial intelligence? The result is Harper, named for Rice's mother's maiden name. Launched in 2024, the company operates as an almost fully autonomous licensed commercial insurance agency. It's a pivot that turns personal history into a forward-looking solution, blending hard-won lessons with cutting-edge technology.

How an AI-Native Brokerage Actually Works

At its core, Harper's platform uses artificial intelligence to streamline the entire insurance journey. Small business owners answer a few guided questions about their operations, team, and risk profile. The system then analyzes data from more than 160 carrier partners to surface tailored options for workers' compensation, liability, and other commercial policies. What once took days of phone calls and paperwork now unfolds in a seamless digital flow.
This isn't just automation layered on old processes. Harper was designed from the ground up as an AI-native insurance brokerage. Machine learning models continuously refine recommendations based on claims history, industry trends, and real-time underwriting signals. Human experts remain in the loop for complex cases, but the platform handles the heavy lifting. The goal is simple: make commercial coverage as intuitive as ordering software, with speed and clarity that traditional brokers struggle to match.

Why $47M Matters for the Future of Commercial Coverage

The fresh capital—structured as a combined seed and Series A round—signals strong confidence in Harper's model. Investors see a massive opportunity in modernizing a sector where small businesses often feel overlooked. The funding will accelerate product development, expand carrier partnerships, and support go-to-market efforts across key industries. For a capital-intensive field like insurance, this runway is critical for scaling trust and technology in parallel.
More broadly, the round reflects a shifting industry mindset. Forward-thinking accelerators have noted that the next generation of agencies will operate with software-like margins and scalability. Harper embodies that vision: a licensed entity powered by intelligent systems, not just salespeople with spreadsheets. This infusion of capital isn't just about growth—it's a vote for a future where insurance feels less like a chore and more like a strategic advantage.

Small Businesses Get a Smarter Insurance Experience

For founders and operators, time is the ultimate currency. Harper's AI insurance brokerage model targets that pain point directly. Instead of navigating opaque quotes or generic policies, businesses receive transparent, context-aware recommendations. The platform explains coverage choices in plain language and highlights trade-offs, empowering smarter decisions without requiring insurance expertise.
This approach resonates deeply with today's digital-native entrepreneurs. They expect tools that integrate with their workflow, adapt to their needs, and respect their attention. By focusing on small to mid-sized companies—a segment often underserved by large carriers—Harper fills a critical gap. The result is coverage that feels personalized, proactive, and built for the pace of modern business. Early users report not just faster onboarding, but greater confidence in their risk protection.

Building Trust in an Automated Insurance World

Adopting AI in insurance isn't just about efficiency—it's about earning trust. Harper addresses this by combining transparent algorithms with licensed expertise. Every recommendation is auditable, and complex scenarios trigger human review. This hybrid model ensures that automation enhances, rather than replaces, professional judgment. For business owners, that balance is non-negotiable when protecting their livelihood.
Rice's candid reflection on past failure also strengthens Harper's credibility. Acknowledging setbacks and prioritizing sustainable unit economics signals maturity to both customers and investors. In an industry where trust is paramount, that authenticity matters. The team's focus on regulatory compliance, data security, and clear communication further reinforces reliability. As Harper scales, maintaining this foundation will be as important as its technological edge.

The Road Ahead for AI-Driven Insurance

Harper's $47 million milestone is more than a funding announcement—it's a signal that the insurance landscape is evolving. As artificial intelligence matures, sectors built on complex data and personalized risk assessment are ripe for reinvention. Harper's AI insurance brokerage model offers a blueprint: start with deep domain pain, apply intelligent automation thoughtfully, and keep the human element where it adds the most value.
For small businesses, this shift promises a future where securing coverage is fast, clear, and tailored. For the broader market, it highlights how legacy industries can embrace innovation without sacrificing reliability. As Harper expands its platform and partnerships, the coming months will reveal how quickly this new model can gain traction. One thing is clear: the era of insurance as a friction-filled obligation is giving way to something smarter, simpler, and built for the businesses powering tomorrow's economy.