Lessons I’ve Learned From Recruiting for 15+ Years

After more than 15 years of hiring for investment teams, portfolio companies, and advisory roles, I’ve realized that most companies approach recruiting the wrong way. They treat it as a one-time event, overvalue resumes, and underestimate the role of systems and culture. Here are three lessons I wish I had learned earlier.

1. Recruiting Should Be Continuous, Not Occasional

Most companies wait until there’s an urgent need to start hiring. The problem? That puts them in a time crunch, forcing them to settle for whoever is available instead of who is best for the role.

The best hiring processes never really stop. They:

  • Keep a steady pipeline so roles can be staffed quickly when needed.
  • Stay open to high-value candidates—if someone exceptional comes along, make room.
  • Encourage unsolicited inbound applications so the best people come to you before you even need them.

For senior hires, this often means long-term relationship building. But for mid-level and junior roles, it’s about speed, process, and always having talent in the pipeline. If you only recruit when you have to, you’re already behind.

2. Hire for Attributes and Fit, Not Just Experience

Early on, I put too much weight on experience—assuming that if someone had done the job before, they’d do it well again. But I’ve seen firsthand that experience alone doesn’t predict success.

At our firm, fit means more than just aligning with our values—it means being wired a certain way. The people who thrive with us:

  • Are highly attuned to business—they don’t just do their job; they understand how their work drives results.
  • Take extreme ownership—no excuses, no passing the buck.
  • Keep things quick and simple—they cut through noise, prioritize, and execute.
  • Apply a continuous test/learn approach—always iterating, improving, and adapting.
  • Knock down barriers, especially in communication—they don’t let silos or bureaucracy slow things down.

This mindset creates a culture of fast learning and adaptation, where the best ideas win and execution is relentless. Hiring someone with the perfect resume but the wrong approach? That’s a guaranteed misfire.

3. Systems and Culture Matter More Than Any Individual Hire

Hiring great people is only half the battle. If your systems and culture aren’t built to support them, even A-players will struggle—or leave.

What a great system and culture is not:

  • It’s not about endless perks or “cool” office spaces.
  • It’s not a free-for-all where people do whatever they want.
  • It’s not a rigid bureaucracy where process kills speed.
  • It’s not a place where underperformers can hide.

What the best companies do have:

  • Clear performance expectations—everyone knows what winning looks like.
  • Fast feedback loops—problems get surfaced and solved in real-time.
  • Strong incentives—rewards align with long-term impact, not just short-term output.
  • A high bar for talent—low performers don’t stick around, and high performers keep getting better.

At NextBold Capital firm, we’ve seen that when the right systems are in place, great hires thrive—and mis-hires quickly self-select out. A great culture doesn’t just attract top talent; it ensures they stay, grow, and elevate the entire organization.

Final Thought

If I could go back and give my younger self advice on hiring, it would be this: Don’t just hire when you have a vacancy. Don’t rely on resumes. And don’t expect great people to thrive in a broken system. Build a culture where A-players want to stay, and as Bill Walsh’s biography goes “the score will take care of itself”.