For years, tax season has followed a familiar script. Your financial advisor tells you one thing. Your CPA tells you another. Somewhere between the two, you become the messenger, forwarding PDFs, digging through email attachments, and hoping nobody missed an important detail.
Miami startup Taxfyle thinks that process no longer makes sense.
When Refresh Miami last spoke with Taxfyle co-founder and CEO Richard Lavina three years ago, the company was focused on connecting taxpayers with licensed CPAs through its marketplace. Since then, artificial intelligence has reshaped the business.
Rather than competing with consumer tax software, Taxfyle now powers tax services for financial advisors, wealth managers, and large financial platforms.
“How do we position our 7,200 CPAs on the platform with our clients to get through this work more accurately, faster, and cheaper?” Lavina told Refresh Miami. “That became the thesis.”
The shift reflects broader changes across the accounting industry. As AI spread through professional services, many firms consolidated through private equity rollups, adopted new software, reduced headcount, and increased prices.
Taxfyle took a different path. “Our goal for the past 36 months has been to increase supply,” Lavina said.
Instead of hiring thousands of accountants directly, the company taps into licensed CPAs who now work in corporate finance, nonprofits, or other industries but still have spare capacity during tax season. AI handles much of the repetitive document processing before a CPA reviews a return, allowing accountants to work faster while maintaining quality.
The company’s focus has also moved further up the financial stack. Rather than selling directly to consumers, Taxfyle increasingly works with registered investment advisors and wealth managers that want tax services to become part of a broader financial relationship.
“How can you offer financial wellness if you don’t offer taxes?” Lavina said.
Advisors can work alongside Taxfyle’s CPAs inside a shared platform where tax documents, returns, and financial information live in one place. Clients still speak with a real CPA when needed, while advisors gain a clearer view of their clients’ overall financial picture.
That strategy has attracted major partners. Taxfyle now powers tax services inside Robinhood’s Concierge offering for higher-net-worth customers, has expanded its relationship with Empower, one of the world’s largest retirement plan providers, and counts Northwestern Mutual among its investors.
“When you get vetted by someone like that, that’s nice product validation,” Lavina said.
The company has also launched a new product called Plan, which helps advisors and clients identify tax-saving opportunities before the end of the year instead of waiting until tax season.
“The purpose of Plan is simply to set up a talking point between you and your advisor,” Lavina said. “Then you can pass it over to a CPA that can do something about it.”
Inside the company, AI has reshaped operations as well. Taxfyle now employs around 50 people, all based in Miami, after moving away from overseas outsourcing. Lavina said the goal isn’t simply to reduce headcount but to give employees broader ownership over projects while AI removes repetitive work.
Despite building Taxfyle in Miami for more than a decade, Lavina said raising venture capital remains easier in the Bay Area.
“The rounds are still bigger. The multiples are still bigger in San Francisco,” he said. “It’s hard to crack that code without moving out there.” Still, Taxfyle remains committed to South Florida, with its HQ in the heart of Coconut Grove.
READ MORE IN REFRESH MIAMI:
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