In the heart of Silicon Valley, there’s a well-worn mantra: “Solve your own problems, and you’ll find your startup idea.” It sounds logical—after all, who better understands a pain point than the person living it?
But what happens when everyone in tech follows that advice? You end up with a sea of productivity apps, AI note-takers, and calendar optimizers—tools built for people who already live inside software. Meanwhile, entire industries—like insurance—remain buried under paper, spreadsheets, and legacy systems that haven’t changed in decades.
Enter Comulate, an AI-powered startup quietly transforming one of the world’s most analog sectors. And their journey? It’s a masterclass in persistence, customer empathy, and the power of looking where others won’t.
This isn’t just another tech success story. It’s a startup story forged in skepticism, refined through deep customer collaboration, and now scaling to eight figures in annual recurring revenue (ARR)—all by rethinking what’s possible in an industry many wrote off as “too hard” to disrupt.
The Unlikely Founders: Two Outsiders with No Insurance Experience
Jordan (CEO) and Michael (CTO), co-founders of Comulate, didn’t come from insurance. Jordan cut his teeth in product management at Asana, inspired by a book—Cracking the PM Interview—that led him to seek mentorship from industry leaders. Michael, meanwhile, was engineer #10 at Brex, watching it explode from a tiny startup to a 900-person fintech powerhouse.
Both were steeped in modern software culture. But neither had ever filed an insurance claim, let alone understood the labyrinthine back-office workflows that keep the $6 trillion global insurance industry running.
So why insurance?
“We realized there’s unsolved problems everywhere,” Jordan recalls. “But in tech, we’re all solving the same problems for the same people. Insurance? It was wide open.”
What they found stunned them: paper-based processes, manual data entry, redundant accounting layers, and workflows so complex they resembled Rube Goldberg machines. And yet, no one had built a modern software solution to untangle it.
The First “No”: A Defining Moment
Their early outreach was met with polite but firm rejection.
“I’m taking this call as a favor… but we don’t need your services. We’re all set.”
That quote—so dismissive, so final—became a rallying cry. They even printed it and hung it on their office wall.
At the time, it felt like a death knell. If one of the largest players in the space didn’t see a need, who would?
But instead of retreating, Jordan and Michael doubled down. They spent weeks on Zoom calls with underwriters, accountants, and operations leads—not pitching, but listening. They asked about edge cases, exceptions, and the “why” behind every step in their workflows.
“We weren’t salespeople,” Michael explains. “We were product people trying to understand the problem deeply. And that built trust.”
One early customer, nearing retirement after 50 years in the industry, later wrote to Jordan:
“Working with you was the first time someone brought in a product that actually understood us.”
That validation was worth more than any term sheet.
The Pivot That Changed Everything: Rethinking Workflows, Not Just Automating Them
Most AI startups today focus on augmentation: helping humans do their existing jobs faster—drafting emails, summarizing documents, or filling forms.
But Comulate took a different approach. They asked a radical question:
“What if the workflow itself is the problem?”
In insurance, decades of regulatory complexity, legacy systems, and intermediary layers created processes that were never designed—they just evolved. A single accounting task might involve five systems, three spreadsheets, and two manual reconciliations.
Instead of building software to mirror that chaos, Comulate simplified it.
“We’d map out their entire process—it looked like a 30-box flowchart,” Jordan says. “Then we’d say: ‘You can actually do this in three steps with AI.’”
This wasn’t automation. It was reimagination.
Think of it like the shift from desktop to mobile. The apps that won weren’t the ones that shrunk websites onto phones. They were the ones—like Instagram—that asked: “What’s uniquely possible on a mobile device?”
Similarly, Comulate asked: “What’s uniquely possible with AI in insurance?”
The answer? Eliminate redundant steps, collapse data silos, and rebuild workflows from first principles.
Why Insurance? The Hidden Goldmine for AI
Insurance might seem like an odd choice for a tech startup. It’s slow-moving, heavily regulated, and notoriously resistant to change.
But that’s exactly why it’s ripe for disruption.
According to McKinsey, over $300 billion is spent annually on manual, repetitive tasks in insurance back offices. Much of this work—data entry, reconciliation, compliance checks—is rule-based and document-heavy, making it ideal for AI.
Yet, until recently, few startups dared enter the space. Why?
- High barriers to entry: Domain expertise is scarce.
- Long sales cycles: Enterprises move slowly.
- Perceived “boringness”: Not as flashy as AI chatbots or crypto.
But as Jordan points out:
“The biggest opportunities aren’t where everyone is looking. They’re where no one wants to look.”
Now, the tide is turning. In the latest Y Combinator batch, 70% of startups are building AI agents for vertical industries—insurance, construction, logistics, healthcare.
Comulate was ahead of the curve. They didn’t chase trends; they followed pain.
The Power of Being “Product-First” in a Sales-Driven Industry
One of Comulate’s secret weapons? Their product-first mindset.
In traditional enterprise software, sales teams often drive the roadmap. Features are built to close deals, not solve core problems.
But Jordan and Michael came from product-led cultures (Asana, Brex). They believed that if you truly understand the user, the product sells itself.
Their early development process was intensely collaborative:
- Weekly calls with pilot customers
- Real-time feedback on prototypes
- Co-designing workflows with end-users
This approach built deep domain expertise—something rare among tech outsiders.
And it paid off. That same company that once said, “We don’t need your services”?
They’re now one of Comulate’s largest customers.
Lessons from a Startup Story That Almost Didn’t Happen
So what can other founders learn from Comulate’s journey?
1. Ignore the “Obvious” Problems
Solving your own problems works—until everyone’s solving the same ones. Look beyond your bubble.
2. Seek Out “Unsexy” Industries
The less glamorous the sector, the less competition you’ll face—and the greater the impact you can make.
3. Validation > Assumption
Don’t assume you know the problem. Talk to real users. Map their workflows. Find the hidden friction.
4. Simplify, Don’t Just Automate
AI’s real power isn’t in speeding up broken processes—it’s in eliminating them entirely.
5. Persistence Beats Permission
That first “no” isn’t the end. It’s data. Keep digging. The truth is often one layer deeper.
The Future: AI as the New Operating System for Legacy Industries
Comulate’s vision extends far beyond insurance.
They see AI not as a feature, but as a new foundation for enterprise software—one that can finally digitize industries stuck in the pre-internet era.
“There are hundreds of billions of dollars spent every year on manual work,” Jordan says. “AI has opened that up into a massive opportunity. And we’re right at the forefront.”
With eight-figure ARR and growing enterprise demand, Comulate is proving that the next wave of tech innovation won’t come from social apps or crypto—but from reimagining the invisible machinery of the real economy.
Final Thoughts: The Startup Story That’s Just Beginning
Three years ago, two outsiders with no insurance experience pitched an idea most thought was crazy.
Today, they’re transforming how one of the world’s oldest industries operates—using AI not to patch the past, but to build a simpler, smarter future.
Their startup story is a reminder that the best ideas often come from asking the right questions in the wrong places.
And sometimes, the biggest “no” is just the prelude to your biggest “yes.”
Ready to rethink what’s possible in your industry?
The next breakthrough might not be in Silicon Valley—it might be in the back office of a 100-year-old company waiting for someone to finally understand them.
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