The archive · Money & Fintech · Strategic decision · 2024-2026
Harper rebuilt the insurance brokerage around AI, won 5,000 clients, and raised $46.8M
YC W25 agency that owns the whole insurance workflow with AI, not just tools; it handles 1,000+ customers a month and raised $46.8M from Emergence.
Harper
What the business is
AI-native commercial insurance brokerage that matches small and mid-sized businesses with 160+ carriers for workers' comp, general, and professional liability — it owns the agency, not just software.
Starting capital：$46.8M combined seed and Series A, led by Emergence Capital, with YC, Lobster Capital, and Peak XV (Feb 2026).
How it started
Dakotah Rice, a Goldman Sachs and Carlyle alum whose family owned an insurance brokerage, had just closed his fintech Poolit in 2023 and admitted he should have shut it down a year earlier. With Tushar Nair, Poolit's former CTO, he first considered building AI tools for existing brokerages — then decided the tools were the easy half and the better bet was to be the brokerage itself. Harper launched in 2024 and joined Y Combinator's Winter 2025 batch.
What happened
Harper took its first customers in October 2024 and by its YC launch was writing over $6M in annualized premiums across 35 states. AI handles submission routing, underwriter follow-ups, document collection, and pipeline management, while proprietary models match each business against Harper's network of 160+ carriers, wholesalers, and MGAs. The result, per the company: what takes a traditional broker five to seven days gets done in one to two, and a sales engine that handles 1,000+ customers a month versus the usual 20-30. By February 2026 Harper said it had more than 5,000 customers.
How it ended up
Still active and scaling. In February 2026 Emergence Capital led a combined $46.8M seed and Series A with YC, Lobster Capital, and Peak XV, and Harper was hiring to grow its engineering team and its brand in middle America — daycares, manufacturers, dealerships, bars, and restaurants.
Background
Harper is a commercial insurance brokerage built around AI rather than an old agency with AI added. Dakotah Rice — whose family owned a brokerage and whose uncle's trucking company was crushed by insurance costs — and Tushar Nair, a former Goldman engineer, first thought about selling AI tools to existing agencies. They decided instead to become the agency, launching Harper in 2024 and going through Y Combinator's Winter 2025 batch.
The bet was that AI could take over the judgment-heavy work of brokering: reading applications, routing submissions, following up with underwriters, and matching each business against carriers. Harper says its AI works across 160+ carriers, wholesalers, and MGAs, cutting a five-to-seven-day process to one or two days and handling more than 1,000 customers a month where a human team handles 20 to 30.
By February 2026 Harper said it had 5,000+ customers, and Emergence Capital led a combined $46.8M seed and Series A with YC, Lobster Capital, and Peak XV. The company's ambition is to become the largest brokerage in the world and eventually the back office for small-business owners — insurance first, then risk, compliance, and beyond.
What has to be true
- Owning the service captures the data every policy produces, and that data feeds the matching model — the work compounds instead of leaking to clients.
- Incumbents run fragmented, manual workflows; an AI-native agency can serve niches the old model cannot scale to profitably.
- Rice's family brokerage background gave him the customer and the credibility to enter a relationship-driven industry.
- The Poolit failure taught him to cut losses earlier and gave the second company a sharper thesis.
What can be applied
When AI makes a service scalable, the strongest position is to own the service, not sell the tool: Harper's data compounds with every policy, and the customer relationship stays in the house.
Aftermath
As of February 2026, Harper had 5,000+ customers, was handling more than 1,000 customers a month, and was using the $46.8M round to grow its engineering team and its brand in middle America — daycares, manufacturers, car dealerships, local bars, and restaurants. The founders' stated endgame was to become the voice for entrepreneurs: insurance first, then risk, compliance, and the rest of the back office.
Sources
- Y Combinator grad and AI insurance brokerage Harper raises $47M
- Harper: Building the AI-Native Insurance Brokerage Every Business Deserves
- Harper: AI-native commercial insurance brokerage
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