Brad McIlwain

Brad has spent his career leading teams, solving complex problems, and figuring out how to make technology work better for the people who depend on it. His background includes organizational technology strategy, IT operations, and building practical solutions across many industries and organizations since 2007. Before joining prpl pineapple, he helped establish and grow a portfolio of technology and service businesses through Solertiae, serving as President before that work became part of prpl pineapple. That experience shaped how he approaches just about everything: understand the problem, challenge assumptions, and don’t overcomplicate something that should be simple.

Today, Brad leads Managed Services at prpl pineapple, where he’s focused on rethinking what technology support can and should look like. He cares about building teams and systems that anticipate problems instead of just reacting to them, and about using technology to create real value rather than adding another layer of complexity. He’s particularly interested in AI and automation, not just for efficiency, but for their potential to create more space for human creativity, connection, and meaningful work. He moves between big-picture strategy and the details of execution because both matter, and a good idea isn’t worth much if you can’t make it work.

Outside of work, Brad lives in East Tennessee with his wife and two kids. They have a small farm, host an Airbnb, and enjoy spending time outdoors. He’s also a classically trained trumpet player, with a little piano thrown in during his early years. That musical foundation has shaped how he thinks about the balance between structure and creativity, and how to bring the two together to make something work.