Fred Voccola
Walk down any street in your town and look at the people keeping daily life running. Electricians, plumbers, air conditioning technicians, and facility crews keep our lights on, our water flowing, and our buildings safe. Yet behind the scenes, many of the small and midsize companies employing these workers are fighting just to survive. On a recent episode of Leaders in Tech, host David Mansilla sat down with Fred Voccola to discuss how artificial intelligence is changing that reality.
Fred Voccola is a technology entrepreneur, philanthropist and board director. Based in Miami, he serves as the Chairman and CEO of Simpro Group (www.simpro.ai). He is the Co-Founder, Vice Chairman, and former CEO of Kaseya. He also sits on the board of Florida International University and serves as chairman of the Cooper Voccola Family Foundation, a nonprofit supporting animal, veteran, and child welfare causes. Voccola is an internationally recognized authority on AI, cybersecurity, hyper-growth business at scale, business/company transformation, crisis management and organizational culture. Find him on X/Twitter each day: @RealFredVoccola.
Throughout his career, Fred has watched how new waves of technology reshape business economics. Today, he believes AI and digital workforces are transforming business economics by enabling small and midsize companies to overcome severe resource constraints, optimize complex operations, and achieve enterprise-level profitability.
The Hidden Struggle Behind Essential Businesses
Most people do not realize how hard it is to run a commercial trade business. Across the globe, roughly twelve million field service companies send skilled workers out to customer locations every single day. Over ninety-nine percent of them are small or midsize businesses with fewer than fifty employees. When storms hit or emergencies strike, these teams act as society's second responders right after police, fire, and medical crews.
Despite how much our modern way of life depends on them, most of these companies survive on razor-thin profit margins of around five percent. Why is it so tough? Getting the right technician with the right tools and the right parts to the right address on time is a massive puzzle. A fifty-person maintenance crew faces daily supply chain and scheduling challenges that rival those of massive aircraft manufacturers. The difference is that a small business cannot afford a giant corporate planning department. When one technician arrives at a job site with the wrong tool or sits stuck in poorly routed traffic, the fuel waste and lost hours wipe out the entire day's profit. Add a global shortage of millions of skilled trade workers, and small business owners end up trapped in constant stress.
From a College Dorm Startup to Building Tech Giants
Fred Voccola understands how technology solves big problems because he has spent over three decades building companies through every major digital shift. Growing up in New Jersey and attending the University of Miami on scholarships, he learned early from his father that technology has the power to disrupt old industries. During his junior year of college in the 1990s, he started a data warehousing software company that helped businesses pull information out of massive mainframe computers so they could finally understand their customers.
That first win launched a career of riding major technology waves. When the internet arrived, Fred helped build Identify Software, creating the world's first application performance monitoring product to fix slow web apps. During the 2008 financial crisis, he co-founded a financial technology platform that helped businesses secure working capital loans using their unpaid invoices. Later, at Kaseya, he saw that local doctors' offices, law firms, and contractors needed enterprise-grade cybersecurity and IT support they could not afford on their own. By building a single, affordable platform for managed service providers, he helped scale Kaseya into a billion-dollar global leader. When public language models emerged, Fred realized AI would be the biggest disruption humanity has ever seen, inspiring him to take the helm at Simpro Group and transform it into an AI-first operating platform.
How a Digital Workforce Levels the Playing Field
For decades, huge corporations held an unfair advantage because they could afford armies of analysts, schedulers, and accountants. Digitalization and AI agents are erasing that gap. At Simpro Group, Fred and his team built an AI operating platform that gives small and midsize contractors a complete digital workforce. Instead of forcing stressed owners to stay up late managing paperwork, intelligent software handles scheduling, material purchasing, billing, and customer follow-ups automatically.
Consider what happens when a fifty-person company finishes its work on time, yet customers pay their bills months late. The business looks profitable on paper, but it runs out of cash because it cannot afford ninety thousand dollars a year for a full-time collections specialist. By deploying an AI collections agent that costs only a few thousand dollars a year, that same small business can collect payments faster and more politely than a human team, cutting unpaid invoice delays by ninety percent. Across the board, replacing manual back-office bottlenecks with digital workers reduces missed appointments and lifts small business profit margins from five percent up to twenty or twenty-five percent.
Leadership Built on Grit, Freedom, and Lifting Others Up
Ask Fred why he continues to work long hours after achieving tremendous financial success, and his answer has nothing to do with money. To him, business is about the joy of the daily grind alongside a loyal team he has worked with for twenty years, treating coworkers and friends like one extended family. More importantly, he is driven by the moment a small business owner hugs him and shares that better profit margins finally allow them to pay for their children's college or retire with dignity.
Fred's leadership style is rooted in personal accountability, free market opportunity, and resilience. He believes that true upward mobility happens when people have the freedom to choose their path, take risks, and earn the rewards of their hard work. Nothing worthwhile comes without sacrifice, and entitlement only holds people back. When life knocks an entrepreneur down, there is rarely a safety net waiting to rescue them. Real leaders pair deep empathy for others with stubborn perseverance, refusing to quit until they find a way to make their vision work.
Preparing Your Business for the AI Reckoning
Looking ahead, Fred sees a massive transformation coming fast. While billions of dollars are pouring into artificial intelligence, he warns that ninety-nine percent of trendy AI startups will eventually fail. The true winners will not be flashy apps, but systems of record that hold real, proprietary business data. Just like a human employee needs company knowledge to do a job well, a digital worker relies on accurate operational data to make smart decisions.
By the end of 2028, Fred predicts the world will employ more digital workers than physical workers, and companies that fail to become AI-first face a harsh reckoning by 2029. This shift does not mean human workers become useless. Instead, the most valuable employees of tomorrow will be people who know how to guide, prompt, and manage a team of digital workers to achieve clear outcomes. Whether you are a student preparing for your first career or a business owner fighting to grow, embracing AI today gives you the power to turn limited resources into extraordinary results.
Author: Jovilyn Abella
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“You’re going to see, you know, the software companies and the enterprises and and and mid-size companies they support that are not AI first. There will be a reckoning between now and 2029. A lot of these companies are going to die, but the winners are going to just explode because the value that they’re providing is just astronomical.”
