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Meet Our Vice President – Dent Wilkens

Meet Our Vice President – Dent Wilkens

February 26, 2026
Vice President, Dent Wilkens

Dent forged the belief that strong partners are an essential component of success through his two decades of experience in the sports business world. As a native of Rochester, he is passionate about supporting enterprises and organizations that anchor our local community. Dent strives to build and support a team that relentlessly delivers innovative solutions and exceptional service to our clients, ensuring IT Insights is a trusted partner for the growth of the businesses we serve.

We sat down with Dent and asked him a few questions we thought our clients and partners would like to know:

Q: What shaped your journey to this point?

A: I’ve had the opportunity to work for and alongside organizations that have had ambitious visions for growth and were never satisfied with the status quo. I am fortunate to have learned from exceptional teammates and leaders who have shaped the way I think about problem-solving, and to a deeper extent, what is possible. I relish the “big wins” – things that we accomplish as a team through hard work and collaboration – hopefully with some fun mixed in along the way.

Q: Where do you focus your energy these days? What gets you excited to dive in?

A: Understanding the unique strengths of team members and maximizing those for impact on our clients and business. Additionally, the learning process of transitioning my experience into a different field of business is energizing and something I’m really enjoying.

Q: What’s the trickiest business or technology challenge you’ve had to navigate as a leader?

A: When I was working for US Squash, we created a $40M national center in the heart of Philadelphia. The project required complex coordination between business units of our organization, numerous vendors, and external partners, with much of the project having to be coordinated through the heart of the pandemic. After years of work, it was incredibly gratifying to stand alongside our team and stakeholders to celebrate the creation of an amazing space that will be the heart of the sport in the U.S. for generations to come.

Q: How do you keep your finger on the pulse as the business industry shifts?

A: It’s important for me to identify experienced individuals and experts in their respective content areas to guide me to the best sources of information and ways to stay current. Sometimes the best method is to simply sit down and listen to what they are excited about in their field and what trends they are seeing. Finding people smarter than yourself and getting them talking is always a great strategy!

Q: What technology trend or tool are you interested in right now? What should leaders be paying attention to?

A: The integration of AI tools is happening so quickly that by the time you believe you’ve learned it, the technology is already in a completely different place. We need to be nimble to keep pace and not get stuck in old processes or ways of doing things, while at the same time not just chasing the next shiny object. It’s important to take a step back to understand your core business challenges and what tools are best positioned to solve them.

Q: What’s the one piece of tech you rely on daily to stay productive and connected?

A: My phone, which unfortunately contains much of the information that I wish my brain was capable of carrying.

Q: What is a skill that you are currently working on developing?

A: By nature, I’m somewhat risk-averse and hesitate to lean into substantive changes. I’ve been fortunate to work with some visionary leaders of businesses and institutions who have shown me that amazing things are possible with the right strategy, people, and willingness to work towards change. I’m grateful for the mentorship of these individuals – and the time they’ve invested in my development – and credit them with my becoming more at home with driving evolution and leaning (sometimes uncomfortably!) into new things.

Q: What’s your best advice for businesses navigating their upward transformation?

A: Don’t be afraid of ambitious goals. That said, it’s essential to ensure that you have alignment of leadership, staff, and important stakeholders about strategy and tactics. Without it, teams can end up working hard and with the best intentions, yet still fail to make meaningful progress.

Q: If you hadn’t gone this route, what career path would have captured your attention?

A: I greatly enjoyed the sports world and its ability to bring together people and communities – I’m grateful to have had the opportunity to work in that space. My secret dream, however, is to be a chef or to run a restaurant – though that’s unlikely to happen since I’d probably eat all the profits, not to mention the time it would take away from my family. I have a ton of respect for everyone in that industry and the work it entails.

Q: How do you recharge outside of work? What keeps you balanced?

A: I’m lucky to have two amazing daughters who keep my wife and me busy – there is nothing better than spending time with them and seeing the people they are becoming. I love playing squash or tennis when I have the chance, and I enjoy being a mediocre golfer for the ~2 times I play per year. We also have two very loveable but poorly behaved dogs.

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Categories:IT Insights Life, Team|Tags:Employee Recognition, IT Team
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