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 received is to just do it and not let anyone stop you - but with one important caveat from my dad: nothing permanently stupid. When I say just go for it, I mean make sure you're okay with the consequences or the outcomes. As long as you reason through that and you're willing to deal with the fallout, don't let anything or anyone stop you. I didn't tell people I was applying for the roofing job because I knew they would say no, and to avoid that argument, I just didn't tell anybody until after I did it. Sometimes you read somebody's resume and they made it sound like the coolest way you could have done that thing ever - so gas yourself up, be your biggest cheerleader, and just do it, because the worst somebody can say is no.

Just do it. Don't listen to anybody. If you think you can do it, do it. Gas yourself up, be your biggest cheerleader, and just go for it, because the worst somebody can say is no. I think young women in particular second-guess a lot and overthink a lot - so just do it. I got the job by buying donuts and showing up after I applied on a whim. Nobody would have advised me to do that, they would have been like 'that's crazy.' But I did it because I'm the one that has to deal with the consequences, and if I'm okay with the consequences, I'm gonna do it, because I'm the only one that has to deal with the fallout. So my advice is to just go. The amount of people that got jobs that maybe didn't know everything but knew they could figure it out - they went for it. Sometimes you read somebody's resume and they made it sound like the coolest way you could have done that thing ever. So present yourself that way, believe in yourself, and take the leap.

The biggest challenge right now is the AI bubble we're in, with software and SaaS being looked at as something that may be going away. Staying ahead isn't enough anymore it's 20 steps ahead now, not just one step. Another major challenge is credibility. I'm often speaking to business owners, PE owners, and executives all executive men who run roofing companies and trade businesses. I think sometimes there's a level of credibility that's just lost being a woman, and having to overcome that over and over again is challenging. But with my personality, I've always had the audacity and haven't been fired from it yet. Like, I'll say 'well, if you wanted to do it that way, you can. That's not math, but you do you.' Doing that is never something they train you on, but it shocks people enough to start a different conversation, where they almost have respect that you had the balls to say what you said. On the opportunities side, the advancement of this software means we can almost do anything now. We can be a really powerful tool for the trades and expand into any market, supporting customers on both a standardization level and a customized level. The flexibility in the software has really improved, so the opportunities to do anything with it are endless. My team in particular, the solutions architects, we're almost like support for every other department - we work with product, we bug bash, we problem solve, we help with building, we enable teams, we do customer enablement trainings, we travel. Within my field specifically, there's no ceiling at the moment, which is exciting.

Fairness is super important to me the value of fair exchange. I'm gonna work really hard, and my team has to work really hard, but there's gotta be a benefit for everybody involved. Justice is really important to me too, like doing the right thing. What's right is right. This makes me fight for my team really hard, because if they're working beyond what their pay or title should require, I'm the first one to call that out. I never saw myself as a manager, but someone has to drive the ship, and I just look at it like I'm willing to drive and willing to take directions. If someone has an opinion about where they think would be better to go, let's go, because I think it's important to motivate a team and drive success by making sure their voice matters - and I mean it, not just like a survey monkey. If they're working really hard and it's not valued, you'll lose good people really fast. I don't want to be treated that way, so maybe it's projecting, but it benefits everybody, so there's no harm in it.