Investing in Harper: The AI-Native Brokerage Rebuilding Insurance

Commercial insurance sits at the foundation of the real economy. Every business - whether a daycare, logistics company, or contractor - depends on it to operate.

Yet the system that delivers it has not kept pace.

Despite trillions in global market size and abundant carrier capacity, insurance distribution remains fragmented, manual, and slow. Businesses often wait days or weeks for coverage, navigating complex workflows handled by overstretched brokers.

This is not a supply problem.

It is a scaling problem.

Complex businesses require real expertise - and historically, that expertise has not scaled.

We’re excited to announce our follow-on investment in Harper’s Series A, led by Emergence Capital, alongside Y Combinator, Peak XV Partners, Antler, 10x Founders, Lobster Capital, Outset Capital, Optimist Ventures, and Pioneer Fund.

We first backed Harper at the earliest stages after sourcing the company through our AI-native signal-based outreach system. At the time, it was two founders working out of an apartment in Atlanta. No product. No team. But they stood out immediately - speed, clarity of thought, and a deep understanding of the problem.

From pre-seed to seed and now Series A, our conviction has only strengthened.

Following our initial investment, Harper was accepted into Y Combinator’s Winter 2025 cohort and went on to raise a strong seed round, where we followed on. We’ve continued to support the company through its Series A.

Harper is led by Dakotah Rice and Tushar Nair, a founder pair that combines deep market understanding with strong technical execution.

Dakotah’s perspective was shaped early. Growing up around small businesses, he saw firsthand how insurance delays and costs could derail otherwise viable companies - a story he later shared in Harper’s announcement.

Tushar brings deep engineering and product experience, enabling the company to translate that insight into a scalable, AI-native system.

Together, they approached the problem differently.

Harper is not selling software into legacy brokerages. They are the brokerage - owning the customer relationship and executing the full workflow from submission to binding.

Their system uses AI to handle the most time-intensive and judgment-heavy components of insurance distribution: reading applications, routing submissions, managing underwriter follow-ups, and coordinating quotes.

What traditionally takes 5–7 days can now be completed in 24–48 hours, as noted in coverage by TechCrunch.

The result is a fundamentally different operating model.

Harper is achieving ~30x higher revenue per sales rep than traditional brokerages, enabled by automation across the majority of operational workflows. A small team is able to process a volume of business that would historically require dozens of brokers.

But the most important signal isn’t just efficiency - it’s behavior change.

Carriers and wholesale partners are beginning to reorganize around Harper’s demand. Teams are being allocated to prioritize Harper submissions. Take rates are expanding as supply competes for access.

This is what early platform formation looks like.

Harper’s go-to-market engine has also proven highly repeatable. By using real-time signals such as job postings to identify active demand, the company has been able to scale efficiently while maintaining disciplined acquisition costs.

This aligns with the broader shift described by Emergence Capital as “AI-native services” - companies that don’t sell software, but own and deliver outcomes.

In just over a year, Harper has reached ~$5M+ in ARR and served thousands of businesses across the U.S.

Every interaction - submissions, quotes, underwriting decisions - feeds back into the system, improving matching and outcomes over time. This creates a compounding data advantage that becomes increasingly difficult to replicate.

“Complex businesses needed real expertise, which was once impossible to scale. AI changes that.”

 -  Dakotah Rice, Co-Founder and CEO of Harper

Looking ahead, Harper plans to expand carrier relationships, deepen automation across additional workflows, and continue scaling its distribution engine.

In a market as large and essential as insurance, this creates the opportunity to build a category-defining company.

We’re proud to continue backing the Harper team as they scale.

Go Deeper: Early Conversation with Harper

We spoke with Dakotah Rice and Tushar Nair early, before much of this traction was visible.

In this episode of our Agentic Podcast, they share how they’re building the AI-native brokerage and why owning the workflow - not selling tools - was the key unlock.