Jonathan Osler

Corporate Counsel

About

Jon Osler is Corporate Counsel, where he advises on vendor contracts, property acquisition agreements, land use, tax, and zoning.  Jon blends legal compliance and business strategy to help support Highland Digital’s project developments.

Earlier in his career, Jon worked as corporate counsel at Intelsat within the general counsel’s office, overseeing contract and regulatory compliance matters. He later entered private practice, founding Osler, PLLC, and served as CEO of a blockchain-based digital trust startup. Jon also contributed to initiatives with the Federal Communications Commission involving the use of financial derivative instruments in federal spectrum auctions, strengthening his understanding of the intersection between complex financial structures, government-led market mechanisms, and infrastructure planning.

Jon holds degrees from the University of Virginia and the College of William & Mary School of Law.