Long before Kyle Plonsky worked at WellSky, he was working on WellSky’s tickets.

At a hosting company in St. Louis, Kyle spent his days on the other side of the queue, handling networking requests from a healthcare technology company he had never set foot inside. He learned the topology, which requests were routine and which ones meant somebody was having a rough afternoon. When the chance came to join WellSky, the company he had been quietly supporting from a distance, it felt less like a career change and more like walking through a door he had already been knocking on.

The path to networking started at home. Kyle's dad is a network engineer, and growing up around someone who could explain why the internet worked, left an impression that never faded. A year into his own career at WellSky, he is now a Team Optiks teammate and is building the kind of work his dad would recognize, with a few modern twists.

The clearest example is Kyle's work on a major infrastructure modernization effort. Over the past year, he has helped migrate hundreds of VPN tunnels from legacy data centers to newer environments, supporting the organization's broader technology transformation. Multiplied across hundreds of connections, the work requires patience, consistency, and a careful eye for detail.

Kyle looked at the current process, saw an opportunity, and built a tool.

His automation streamlines much of the work behind provisioning VPN connections, helping teams move more quickly and consistently through the process. Tasks that once required a series of manual steps now flow through an automated workflow, allowing engineers to focus more on oversight and validation than repetitive execution. The result is a more consistent experience, with deployments and documentation handled in a standardized way that makes ongoing support easier for the entire team.  

This runs through everything Kyle is excited about right now. He is deep in Terraform, expanding into cloud platform work, and has become an enthusiastic user of GitHub and Claude as a thinking partner when designing something new.  

If you ask him what makes Team Optiks work, he does not lead with the technology. Kyle talks about his colleagues who answer questions without making you feel small for asking and who make the team enjoyable to be part of on ordinary Tuesdays, not just during the wins.

Outside of work, Kyle’s two boxers – Madi and Arty – bring the specific brand of chaos that boxers are known for. There is a home automation habit that will surprise absolutely no one, because of course the guy who automated VPN deployment also automated his living room. Hiking, camping, and kayaking fill the weekends, with a Pacific Northwest road trip on the horizon. Then there is the ongoing negotiation between a fitness goal and a Chick-fil-A habit. He is not going to pretend he is winning that one.

Kyle was recognized recently for his work and admitted to feeling a bit of impostor syndrome about it. One year in, he has gone from managing WellSky tickets from across a vendor boundary to building tools that improve the process behind them. For someone who still feels like he's finding his footing, it's been quite a year.

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