Jonathan Osler

Corporate Counsel

About

Jon Osler is a corporate attorney and regulatory strategist who serves as counsel to Highland Digital. With over a decade of experience, Jon specializes in structuring real estate and capital transactions in tightly regulated environments. His background includes contributions to spectrum auction policy at the FCC and advising on large-scale data center property acquisitions across Northern Virginia. He combines legal precision with a deep understanding of land use, tax policy, and zoning frameworks—key to navigating the complex regulatory landscape of digital infrastructure. Jon holds a JD from William & Mary and a BA from the University of Virginia. Jon enjoys golfing, boating, and working on his rusty old Jeep CJ5.