After two decades spent living between airports and time zones, I’ve had plenty of time to reflect on what leadership really means.

Looking back, one thing strikes me: leadership has changed.

In tech — and especially in SaaS — the pace has accelerated dramatically.Speed is no longer optional.Status quo and compromise? They have no place anymore.Teams want to win. And they want to win now.

It was in this environment that I learned two of my most important leadership lessons.

💥 1. Forget the clichés about hiring

The best talent doesn’t always come from where you expect.

Some of the strongest salespeople I ever hired came not from business schools or big tech companies, but from the army or even professional football.

What mattered wasn’t the résumé. It was the mindset:

• Intelligence

• Perseverance

• Adaptability

• Integrity

• And that extra spark of drive that sets someone apart

These qualities became my compass for hiring decisions, reinforced by the timeless advice of John McMahon.

💥 2. Make decisions. Fast.

The worst mistake a manager can make is waiting.

Waiting to act on a team member who isn’t performing.Waiting to adjust pricing that clearly doesn’t fit the market.

Every time I waited, I paid the price.

One of the toughest but most impactful calls I ever made was changing SaaS pricing to make the product stickier. Painful in the moment — but game-changing in the long run.

Looking Back

With hindsight, there are decisions I would make again without hesitation.Building diverse teams with unconventional backgrounds is at the top of that list. That richness of experience was always a massive performance driver.

But there are also things I would approach differently. For example: training managers on the product. Too often, managers are “just” managers. But in SaaS, they need to understand the engine — every gear, every lever — to truly help their teams grow.

Final Thought

20 years of flights, takeoffs, and landings.And with them, countless leadership lessons learned at high altitude.

Some timeless. Some hard-earned.All of them invaluable.