I co-founded CoverWallet. We built it into one of the first successful insurtech exits. Aon acquired us. Wall Street Journal wrote about it. Hank Greenberg invested. From the outside, it looked like a success story.
Inside, I was drowning.
I was the one person responsible for the actual books: billing, reconciliation, and every counterparty payment flowing through the company. Everyone else on the executive team was focused on topline growth. I carried the financial truth alone.
My last eighteen months at CoverWallet were the hardest of my career.
And when I left, I made a decision.
No one should ever have to go through what I went through.
What CoverWallet Taught Me About Insurance's Broken Back Office
Our average premium at CoverWallet was $1,200. Our average number of counterparties per policy was four: us, the insured, a wholesaler, and a premium finance company.
Think about the complexity of having only $120 of commission to solve the operational load of keeping that policy alive.
We started as a retail agency. Then we launched CoverWallet for Agents, which was essentially a wholesale business. Then we started writing MGA program business. Every new role brought a completely different set of receivables, payables, and terms of trade with our counterparties.
We never invested in the technology for it. I just kept hiring temp workers, training them myself, and building a massive network of spreadsheets. By carrier. By platform. By line of business. Run every month.
We got through it. But it cost us.
Every time there was a customer review complaining we took too long with their refund, that was me. Every time Liberty Mutual called about unaccounted return premium, that was me. Every time an agent in our wholesale network said we never paid their commission, that was me.
"What is going on? This is just basic matching and math, right? Just get it done."
That is what people said to me. As if I didn't know. As if I wasn't working nights to hold together a reconciliation process that was never designed for this level of complexity.
I have two degrees from MIT. Everyone on my team was smart. It wasn't about intelligence.
The tools simply did not exist.
When those systems are fragile, growth doesn't solve the problem. It makes it worse.
What I Found Inside the World's Largest Brokerage
After Aon acquired CoverWallet, I thought: finally. Let me see how the big companies solve this.
They don't.
They just add people. My team of six became a team of fifty within one year. Same spreadsheets. More bodies.
We had money now. We could buy the right solution. But every vendor was a point solution. Billing here. Payments there. Reconciliation somewhere else. Cracks between all of them.
And then I realized something that changed everything.
Every product manager runs the analysis and says: 80% of transactions are fine. This isn't going on the roadmap.
They forget the second part of the 80/20 rule.
The 20% of transactions that aren't fine? That's where 80% of the work is. That's where relationships sour. That's where Liberty Mutual calls you about $2.5 million and your CEO gets dragged into a conversation that should have been automated.
It doesn't matter that 80% of your transactions with a carrier went smoothly. When you're managing millions of dollars at the relationship level, the 20% is all anyone sees.
Every vendor I looked at, from Applied to Vertafore to Guidewire, was solving the easy 80%. The painful 20% was left to spreadsheets, email chains, and people.
Once I understood that, I couldn't unsee it.
The Invisible Layer Holding the Industry Together
Over time, my perspective shifted again.
I started thinking about the people across the insurance industry who sit closest to this complexity.
Billing teams. Reconciliation analysts. Finance operators.
These are the people responsible for ensuring that billions of dollars moving through the system actually reconcile.
They operate in the background.
When everything works, no one notices. When something breaks, they are expected to fix it immediately.
This layer of work is essential. And largely invisible.
It carries an enormous cognitive burden.
And yet the tools supporting it often amount to spreadsheets, legacy billing systems, and institutional memory.
That's not a sustainable operating model for one of the largest financial industries in the world.
Building the Infrastructure the Industry Actually Needs
Functional Finance is our attempt to fix this.
We are building financial infrastructure specifically designed for the complexity of modern insurance distribution.
Infrastructure that understands how insurance money moves.
Infrastructure that makes reconciliation deterministic instead of manual.
Infrastructure that replaces fragile operational processes with systems that can scale.
Because the reality is simple:
Insurance doesn't just need better workflows. It needs better financial infrastructure.
A Final Thought
If I reduce the motivation behind Functional Finance to one sentence, it would be this:
I experienced firsthand how essential, and how undervalued, financial orchestration is in insurance, and I refused to continue operating in a system where that work was treated as secondary.
So we're building the system that should have existed all along.
Ready to see what we've built?
The infrastructure Rashmi describes is real, running, and available for operators who are done reconstructing what happened.