Rylan Oakland’s Jackson story began with one goal: get his foot in the door. He originally applied for an Administrative Assistant position, willing to take whatever opportunity came his way. While that role wasn’t quite the right fit, Jackson found one that was. Since then, Rylan has grown through the organization as a Project Engineer, Project Manager, Division Manager, and now Vice President of Operations.
Today, Rylan oversees project operations across the company, helping teams deliver exceptional work while supporting the people behind every project. Known for his steady leadership and calm approach, he believes successful projects are built through preparation, accountability, and strong relationships.
Outside of work, Rylan enjoys spending time with his wife and four kids, hauling the camper-and-boat combo to his favorite lake, and making the most of Montana summers. If you’re planning to share a meal with him, don’t wait, he’ll probably be finished before you’ve taken your third bite.
