
Kyle Sylvester: Lifting others up lifts you higher
First National Financial LP
Sep 4, 2025
mins
Kyle Sylvester has grown a successful IT career by relying on a lesson he learned from his grandfather and father – build up the people around you to build your own career.
Take us back to the beginning of your career at First National.
KS: I started in September 2015 as a Help Desk Support Specialist. My job before First National was doing break/fix work at Geek Squad. My wife was pregnant, and I wanted something more steady and stable. I progressed quickly, moving into the role of Senior Help Desk Support Specialist. In 2019, I became Supervisor, followed by Manager in 2020 and then Director and Team Lead in 2023.
What was your first year like?
KS: It was really exciting and nerve wracking at the same time. We were a small team of eight when I joined. Everyone was so friendly and welcoming. My team worked with me to show me the ropes and get me on board. Their trust gave me the confidence to spread my wings. There was so much to learn, and I was trying to absorb everything. Every department has a different system or distinct methodology. I had to learn how everything worked so I could support it. I came with an IT background, but I had to understand how users were interacting with IT in every department.
What was your “I’m in” moment?
KS: When I joined First National, the company was using an older operating system and was trying to transition to virtual machines. I proposed a full operating system upgrade. I had to work with developers, QA and infrastructure teams. But I also had to engage one-on-one with individual users in each department to learn about what they do, how they work and document their feedback as they were testing. It was a massive undertaking. That project solidified my position and contributed to my personal brand. I became known and developed strong relationships across the company.
Describe some milestones in your career.
KS: I’ve been shaped through the various roles I’ve had. Getting to work with so many amazing and talented technicians has left a huge impression on me. I’ve always worked closely with my team. Even if I was championing the project, we were successful as a team.
What stamp have you put on the business?
KS: I’ve always heard about a perception that IT technicians can be unapproachable. I wanted to change that at First National. Technical problems are stressful – for us in IT and even more so for people who aren’t technical. I made it my mission to foster an environment where everyone knew that if they had a problem, they could come to IT, and we would work with you. IT has a friendly face at First National, and our team members are known by name. We have strong relationships across the company.
What are you most proud of in your career?
KS: My team, its growth and success. I wouldn’t be where I am without them. We were a team of eight when I started and we have more than tripled since then. We’ve built a strong culture of collaboration, resilience and continuous improvement. No matter what gets thrown at us, we find a way to get it done together. Every day, we are working to become better and build something stronger and more efficient for First National. When I joined First National, there was an openness to innovate and an opportunity to improve existing systems. I took that on with the upgrade of operating systems and helped bring First National forward in the technology space.
Any favourite memories?
KS: There have been so many times throughout the years when we had to work late to get something resolved such as a large computer deployment or software release. When you’re working that hard with that kind of urgency, you get to know your team in a completely different light and establish unbreakable bonds.
Which one of First National’s values resonates with you most and why?
KS: We earn trust. Trust is one of the foundations of everything I do in IT. For example, when we are asking people for honest and candid feedback, we have to build trust, so they share openly. As a manager, I’m in there with my team. If we are going to struggle, we struggle together. I let them know that I’m human too, I see their struggles, I can empathize and always stress working together to find a solution. I wouldn’t be in the position I’m in today if it wasn’t for the trust I’ve built.
Why are our events such as Black History Month, International Women’s Day and Pride so important and such meaningful ways to celebrate diversity?
KS: It’s important to recognize and celebrate our differences, diversities, successes and struggles. I’m West Indian. Most people don’t know that from seeing me. But I’m able to share my story and learn from others’ stories as well. The more we can learn and take away from each other, the more able we are to create a better future for ourselves and everyone around us.
What advice would you share with people growing their careers at First National?
KS: I’ve never seen my career as something I grew for myself. My grandfather built his own business, and my father took it over from him. They never gave me instructions. I saw how they treated others, helped others and gave people chances when others didn’t. They embraced people who wanted to learn and supported those who asked for help. If you want to help your own career, build up the people around you. If you lift people up, they will lift you higher.
Any final thoughts?
KS: I’ve grown tremendously in 10 years and watched those around me grow as well. The IT department has grown exponentially. As has the company itself. I’m in awe when I stop to think about it. There is so much more I want to do. And there is so much more than can and will be done. Keep your eye out for all the amazing things my team and I are cooking up and will bring to the table.
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