Why Your Talent Strategy Will Determine If You Survive The Next Five Years

Here’s a hard truth most CEOs don’t want to admit: Your talent strategy will either make your company unbeatable—or irrelevant.

After building multiple companies and leading teams of tens of thousands of people over the past 25 years, I can tell you the biggest mistake leaders make is believing talent strategy can be copied. They read a book, hire an HR consultant and assume there’s a universal playbook for managing people. There isn’t.

At Simpro Group, we see this every day. The success of our customers—commercial and residential trade businesses—depends entirely on how well they can attract, train, retain and empower skilled people.

Your talent strategy must be as unique as your business model. Anything less will kill your competitive edge. Here are six .principles for building a talent strategy that actually works.

1. Build from Reality, Not Best Practices

Every company’s talent DNA starts with one thing: the business you’re actually in.

When I led Kaseya, our customers were small and midsized business owners. Their livelihoods were personal, and if their business had a good month, their families felt it. If it had a bad one, they felt that too. That reality shaped everything about how we built our teams. We needed people who could build relationships for years, not quarters; employees who treated every customer’s success as if their own paycheck depended on it.

The same can be said about the trades, and we all feel the impact. If technicians can’t get to a service in time, the world goes without electricity, plumbing or cool air—the basic comforts we all rely on. And if those businesses don’t get paid on time, their families suffer, their businesses suffer and ultimately, so does modern society.

That lesson shaped the culture at Kaseya and remains the driving force at Simpro Group. While most software companies tolerate 25 percent turnover, that model would have destroyed us at Kaseya. At Simpro, that lesson continues. Our success depends on building teams who deeply and authentically understand the trades—electricians, plumbers, HVAC technicians and service professionals who keep the world running.

For other companies—say, retail or high-velocity sales—constant turnover might actually work. The point isn’t that our model was right. The point is that it’s unique to us and serves our customers.

2. The CEO Is Now the Chief People Officer

Let me be clear: If you’re the CEO, you can’t outsource talent strategy to HR.

If human capital is your biggest asset (and it is), then leading that capital is your job. Delegating that responsibility is the equivalent of saying, “Finance can handle profitability; I’m too busy.”

In the 1990s, most companies treated IT as a cost center. CIOs weren’t at the table. Fast-forward 20 years: Technology is the business, and the CIO is as critical as the CFO.

The same transformation is happening with companies’ people strategy. The CHRO is becoming the new CIO—a strategic driver of competitiveness. And if your CHRO isn’t designing an AI-ready workforce, your company’s clock is ticking.

AI is rewriting every job description on earth. If your teams aren’t “AI-first” in how they work, they’re already behind. CEOs who don’t lead that transformation personally will find themselves running companies that can’t compete.

3. Build Your Own Talent Pipeline—Don’t Rent It

When I started building tech companies in Miami in the early 2000s, everyone said, “You’ll never find the talent.” They were half right: There weren’t many ready-made engineers or product people.

So, we built them.

At Kaseya, we partnered with Florida International University and Miami-Dade College, two institutions filled with hungry, hard-working, first-generation Americans who wanted a shot. These students didn’t come from privilege; they came with something better: grit.

We invested in them, trained them and taught them the business. And guess what? They became some of the best people we ever hired.

If you want loyalty, don’t buy it—build it. “Grow your own” is a competitive strategy.

4. Prepare for AI’s Thousand-Fold Shockwave

Every knowledge job in the world is being rebuilt right now by AI.

This is not another “efficiency tool.” It’s not email or spreadsheets. This is a thousand-fold leap in capability.

I saw this movie before. In 1992, during my first internship at Lockheed Martin, there was one personal computer for the entire finance department. I ran Lotus 1-2-3 reports for 10 people. Four years later, everyone had a computer, and if you didn’t know Excel (which had replaced Lotus), you were unemployable.

AI is that transformation on steroids.

Sales reps will soon manage armies of AI copilots. Developers will orchestrate AI-driven build pipelines. Marketing teams will generate and deploy entire campaigns in minutes. We are already witnessing this at Simpro Group. Our engineering teams are developing a platform that streamlines our customers’ workflows, transforming complexity into profit.

If you aren’t training your people for this right now, you’re handing your competitors your market share on a silver platter.

5. Stop Pretending You Can Keep Everyone

Retention matters, but let’s be real—you can’t keep everyone, and you shouldn’t try.

There’s a “salary cap” in business, just like in sports. You can’t keep every superstar forever. The smart companies build deep benches. They know who’s next up.

Succession planning is a survival tactic. Whether you have 20 people or 2,000, someone will eventually leave, get sick or burn out. Hope is not a plan. You need playbooks for every key role—temporary coverage, recruiting pipelines, onboarding processes.

6. Make Talent Strategy a Daily Habit

The most common excuse I hear from CEOs is: “We don’t have time for talent strategy.”

That’s like saying you don’t have 20 minutes a day to exercise. Everyone has the time; they just don’t prioritize it.

Spend 20 minutes a day thinking about your people. Who’s performing? Who’s at risk? Who’s your next leader? Who needs coaching? If you do that consistently, you’ll build an unstoppable culture.

Talent strategy isn’t a quarterly initiative. It’s daily leadership. The companies that will dominate the AI-first era won’t necessarily have the best products or the biggest budgets. They’ll have the best people—aligned, trained and ready to run through walls because they believe in what they’re building and who they’re building it with.

AI will create a thousand new advantages. But none of them matter if you don’t have the talent to use them.