Gayle Rourk

I attribute my success to pure grit. I've worked really hard, and whenever I didn't know something, I just saw it as something I had to learn. When we were having issues with our automations, I just learned Python - and this was before we had Claude or other tools to make it faster. I just learned whatever the gap was to get me to the next step, no matter what it took. I've also been incredibly fortunate to have mentorship from Victor, the CEO and business owner of the roofing company where I started. He didn't have to mentor the way that he did, and I don't think I'd be here without that. He always trusted me - not a certificate or a degree, just me. When I started moving to the IT side, it wasn't 'oh, you don't qualify.' It was 'I know you can do it. Here's the things that you're gonna have to learn,' and then he would give me the opportunity. That was really cool. He helped me develop the professional, corporate, and MBA-type skills that I didn't have from traditional education, and I benefited tremendously from being close to how the business operated.

The best advice I’ve ever received is simple: just do it. Don’t let anyone stop you.

My dad added one important caveat: don’t do anything permanently stupid.

When I say “just do it,” I don’t mean act without thinking. I mean take the time to understand the possible consequences and decide whether you’re willing to live with the outcome. If you are, then don’t let fear, doubt, or other people’s opinions hold you back.

When I applied for my first roofing sales job, I didn’t tell anyone beforehand because I knew most people would tell me not to do it. Rather than argue, I applied anyway and told them after the fact.

Sometimes you’ll read someone’s resume and think they took the coolest, most confident path imaginable. The truth is, many of them simply took a chance and backed themselves.

So gas yourself up. Be your own biggest cheerleader. Take the shot. The worst someone can say is no, and a no rarely hurts as much as wondering what would have happened if you’d tried.

My advice to young women is simple: stop waiting until you feel completely ready.

If you think you can do it, go for it. Believe in yourself before anyone else does. Too many women spend their time second-guessing, overthinking, and talking themselves out of opportunities they’re fully capable of handling.

One of the most important lessons I’ve learned is that confidence often comes after action, not before it.

I got my first roofing sales job by applying on a whim, buying donuts, and showing up in person. Most people would have told me that was crazy. Maybe it was. But I was the one who had to live with the outcome, and I was willing to accept whatever happened. That’s the key: if you’re comfortable with the potential consequences, don’t let other people’s fear make decisions for you.

The truth is, many successful people didn’t have every qualification or every answer when they started. They simply believed they could figure it out and took the chance.

So be your own biggest cheerleader. Take the leap. Bet on yourself. The opportunities that change your life rarely come after you’ve eliminated every doubt—they come because you were willing to move forward despite it.

One of the biggest challenges in my field right now is navigating the AI boom and the uncertainty it’s creating across software and SaaS. Staying ahead of the market is no longer enough—you have to be thinking twenty steps ahead, not just one. The pace of change is accelerating, and companies that aren’t constantly evolving risk becoming irrelevant very quickly.

Another challenge is credibility. Much of my work involves advising business owners, private equity leaders, and executives—many of whom are men leading large trade organizations. As a woman in those conversations, there are times when credibility isn’t automatically granted, and you have to earn it repeatedly. Overcoming that can be challenging, but I’ve found that confidence, expertise, and a willingness to challenge assumptions go a long way. Sometimes the most effective thing you can do is say what everyone else is thinking but isn’t willing to say. It may not be in any leadership training manual, but it creates authentic conversations and, ultimately, respect.

On the opportunity side, I’ve never been more excited about the future. The advancement of technology means we’re reaching a point where almost anything is possible. The flexibility of modern software allows us to support customers at scale while still tailoring solutions to their unique business needs. For the trades in particular, the potential impact is enormous.

My team, Solutions Architecture, sits at the intersection of nearly every part of the business. We partner with product teams, support development and testing, solve complex customer challenges, enable internal teams, lead customer training, and influence strategic direction. We have visibility across the organization and the ability to drive meaningful change.

What excites me most is that there really isn’t a ceiling right now. The technology is evolving, the industry is evolving, and the opportunities to create value are expanding every day. It’s a field where curiosity, creativity, and execution are rewarded, and that’s what makes it such an exciting place to be.

The values that matter most to me, both professionally and personally, are fairness, integrity, and accountability.

Fairness is probably the biggest one. I believe in fair exchange: if people are working hard, creating value, and going above and beyond, there should be recognition, opportunity, or reward that reflects that effort. Everyone involved should benefit from success, not just a select few.

Integrity is equally important. I’ve always believed that what’s right is right, even when it’s inconvenient. That mindset influences how I lead, how I make decisions, and how I advocate for others. If I see someone consistently operating beyond what their title, compensation, or role requires, I’m going to speak up. I care deeply about making sure people are treated fairly and that contributions are acknowledged.

That perspective has shaped my leadership style. I never set out to be a manager, but I view leadership as being willing to steer the ship while remaining open to input from the crew. My job isn’t to have all the answers—it’s to create an environment where people feel comfortable sharing them. The best ideas can come from anywhere, and I believe teams perform at their highest level when people genuinely feel heard and valued.

More than anything, I want people to know their voice matters. Not in a performative way, and not because a survey says it should, but because engaged, respected people do their best work. When organizations fail to recognize effort or listen to their teams, they lose great talent. I never want to lead that way.

At the end of the day, I try to treat people the way I would want to be treated—with fairness, respect, and honesty. I’ve found that’s not only the right thing to do, it’s also what drives the strongest teams and the best outcomes.