About TaxRails

The last week of quarterly filings, I was in the hospital—with a PICC line in my arm—and I was the only one who knew how to complete the tax filings for our clients. The system we were using was so complex and opaque that no one else could reliably take over. I was trying to troubleshoot from a hospital bed. It didn't go well. Deadlines slipped. Stress escalated. Everyone—our team, our clients—felt the consequences.

That experience forced a painful realization: even with a smart, capable team, filing accurately was reliant on me. The learning curve of our filing software was simply too steep and too manual for a normal person to step in on short notice and take over.

If you've ever been responsible for filing U.S. employment taxes at scale, you already know this feeling. You know what it's like to see strange variance, You know what it's like to try and work out mid-year opening balances. You've patched together workflows, and worked weekends because you were the only one on your team that had any hope of working it out.

That's who we're building for.

TaxRails is the infrastructure layer I wish we'd had. It's not a bot, a form filler, or an API wrapper over legacy software. It's a programmable foundation for compliance—designed for teams that are responsible for taxes.

We're building for the edge cases. For the long tail of jurisdictions. For the people who want to help their companies do something ambitious without tripping over payroll tax.

We can't make the U.S. tax system simpler. But we can make it understandable, testable, and reliable—so that the person responsible for tax filings isn't the single point of failure. You should be able to take a sick day, go on parental leave, or step back without fearing the whole system will break.

In short: we want you to sleep well at night, knowing your tax obligations are in a good state.

If that’s the kind of peace of mind you’re looking for, I’d love to hear from you.