Why We Bet on Insurance, and Why the Industry Bet on Us.

Two and a half years ago, Anshu and I made a bet that most of our peers in Silicon Valley thought was strange.

We bet on insurance. We bet on the actual industry. The agents and brokers. The 300 years of contracts and data. The professionals who quietly hold together the risk fabric of American business with grit, relationships, and yellow legal pads.

Today, Outmarket AI is announcing $17 million in Series A funding, bringing our total funding to $21.7 million. The round was led by Permanent Capital Ventures, with participation from SignalFire, Fika Ventures, TTV Capital, Dash Fund and senior industry executives. That last group is the signal worth paying attention to - when the practitioners themselves write checks, the thesis is no longer theoretical.

But the real story of this round is not the investors. It is the 250+ agencies who chose to partner with us in the year since we launched the product.

The people who actually got us here

Every line of code and every workflow came from a conversation with an agency, producer, account manager, or principal who opened their playbooks and showed us where it hurt. Many of the top 100 U.S. brokers let us into their new business and renewal cycles. A real time commitment. They did it because it mattered to their clients. Producers called on Friday afternoons to tell us Outmarket caught something on a new account that the previous broker had missed. Details. That is what Outmarket is built from.

None of this was in our investor deck. It is the reason that there is a deck at all. This round is for our customers. We are stewards of what they have built. We do not forget that.

Where we came from

Between the two of us, we spent roughly four decades inside Uber, Meta, IBM, and Ethos. Anshu built large-scale machine learning, text mining, and data systems at companies that defined what modern data infrastructure even meant. I led the platform team at Uber, shipped ad products at Meta, and went on to lead products at Ethos ($LIFE), where we built both the consumer and agent distribution channels from the ground up.

That last chapter is where the bet was actually placed. Building Ethos required speaking with more than a hundred independent agents. Kitchen tables. Strip mall offices. Multi-generational agencies in towns most of our Bay Area friends could not find on a map. What we saw in those visits did not match anything we had read about the industry in the tech press.

We saw extraordinary professionals doing extraordinary work with tooling that was no longer keeping up with the demands of the craft. That observation became the company. The conviction came from our customers.

What the industry knew first

The insurance industry has been called slow, resistant, stuck. The facts are to the contrary.

Insurance has always been a game of probabilities and complex contracts, run by professionals doing the work of lawyers without law degrees, data scientists without CS degrees, and financial advisors without Wall Street pedigrees. For decades, technology showed up at their door with clunky portals and data entry forms, asking them to spend more time documenting work than doing it. The industry wasn't slow. The technology was insufficient. Low adoption was a rational response to a missing value proposition.

Our customers knew this long before we did. They weren't waiting for permission to adopt AI; they were waiting for AI that understood how they work. The moment we put something real in front of them, they ran with it faster than most enterprise software has ever seen. That's not a Silicon Valley story. It's a story about practitioners who have been ready for a very long time.

Why insurance agencies win this cycle

There is a quiet consolidation happening across agencies and brokerages. Small books are being shed because unit economics never worked. The producer pipeline is tightening as a generation approaches retirement. Complexity is compounding faster than anyone can absorb it. Cyber, Climate, Social inflation, AI exposure itself. America is dramatically underinsured across nearly every line, and the gap is not a product problem. It is a distribution problem.

The economic story underneath this is straightforward. When experienced supply meets rising complexity and rising demand, pricing power and operating leverage move to the practitioner who can scale. The producer who used to run 80 accounts will run 240 to 300. The advisory practice that used to take a decade to grow will take three years. The underinsurance gap that has resisted closing for a generation finally becomes economic to serve.

What we have built together

We now run production workflows across Commercial Lines, Benefits, and Personal Lines, covering the work that fills the day in any agency. Quote comparison, policy review, renewal comparison, coverage gap analysis, tower analysis, claim denial challenges, and loss runs extraction across every major carrier format. A Proposal Builder that has replaced hours of document editing with a few clicks and a polished proposal in minutes. Excel workflows that round-trip between brokers and underwriters with field-level intelligence, so the spreadsheets that used to bounce back and forth for days now resolve in a single pass. A data intelligence layer that turns the agency's own book of business into answers, benchmarks, and dashboards in plain English, with no SQL and no BI team in the loop.

There is no other platform in this category that comes close to this breadth, and it is not a close comparison. Most of what the market calls AI for insurance is a handful of point solutions wrapped in a product name. Outmarket is the entire surface of the work, end to end, in one platform that an agency can actually run their business on.

And then there is the custom workflow builder, which is the surface we are most proud of. Our customers are using it to encode their own playbooks, their own QA standards, their own back-office processes. When many of our customers started running workflows they built themselves more than the ones we ship, we knew our platform is becoming the backbone of this industry.

With foundations to scale, we built Deep AMS integrations with Applied Epic, Vertafore AMS360, ImageRight, HawkSoft, and Nexsure. We hardened our processes to get to SOC 2 Type 2, ISO 27001, HIPAA, and GDPR compliance. We invested in single-tenant deployment architecture. A multi-model gateway that routes to the best model for every task. Fully isolated infrastructure in Canada for our PIPEDA customers. None of this got built in a vacuum. All of it was based on a feedback loop with the people doing the work.

Finally, the impact is what matters, and our customers tell us about it every week. Outmarket in its early releases gave producers and account managers 12 to 15 hours back per week. And this number only grows with increasing capabilities and integrations of Outmarket. It cuts E&O errors by up to 70%. It scales the expertise of the agency, so a brand new producer is now operating with the rigor of a 20 year veteran. It drives revenue growth, because every hour saved is an hour redirected to clients. And agencies do not need weeks to onboard; most are in production on the same day!

Outliers building Outmarket

There are 40 of us building Outmarket today. We call ourselves Outliers, and we mean it. Every person on this team chose to point their craft at an industry that most of their peers overlooked. That is not a small choice. It shapes who we hire, how we work, and what we build.

We believe this is the deepest insurance bench any company at our stage has ever assembled. That is a strong claim. We stand behind it.

More than half our Outliers come directly from inside this industry. Former producers. Former account managers. Former agency principals. Former underwriters. People who actually sat across the desk from a client and explained why a coverage limit needed to move. People who built renewal books from zero. They did not learn about this industry from a podcast. They lived it.

The other half of our Outliers come from Uber, Meta, IBM, Salesforce, Docusign, Ethos, and the best technology companies in the world. Engineers, researchers, and operators who have shipped systems at scales most companies will never touch. People who have spent careers managing data, ads, websites, pipelines, algorithms that literally supported billions of customers and billions of dollars of revenue. People whose craft is at the absolute frontier of what technology and AI can do.

Putting these two halves in the same room, on the same problems, every day, is the entire game. The insurance side keeps the technology honest. The technology side keeps the insurance side ambitious. Neither one works without the other. Most companies pick one and pretend the other does not matter. We refused to.

That combination is hard to assemble. It takes a lot of trust to keep everyone aligned. But it is the only way to build something that holds up under the weight of real insurance work. The contracts are too complex, the workflows are too nuanced, and the stakes are too high for any other approach. You cannot fake this bench. You cannot speed-run it. You have to build it. We chose to, and we are looking forward to the adventure.

What this round unlocks

This funding is not about us getting bigger. It is about us getting deeper, and going after the bigger thing.

The bigger thing is this. The insurance industry runs on workflows that have been stitched together across decades of policies, AMS systems, carrier portals, email threads, spreadsheets, and PDFs. Every agency we work with is fighting the same fundamental problem, which is that the work lives in a hundred places and no single system holds the truth. We believe the next decade belongs to the agency that runs on a single intelligence layer that sits above all of it. A layer that reads every document, understands every policy, knows every client, and can act on behalf of the people doing the work. We are building that layer.

This round lets us go faster on every surface our customers tell us is changing how they work. Deeper investment in Proposal Builder, Custom Workflows, AI Policy Checking inside AMS, Loss Runs, and Data Intelligence. A deeper data platform underneath all of it, because the agency that can leverage its data wins. More integrations, more carrier connections, more places where Outmarket plugs in and starts removing friction immediately.

The vision has always been simple. Insurance is one of the most important industries in the world, and the people inside it have done extraordinary work for centuries with tools that could only take them so far. AI changes that, finally. We are going to build the platform that lets the next generation of agencies operate at a level the industry has never seen before.

That future belongs to you. We are here to deliver it.