Founder

Jim Reiland has over 20 years' experience in the legal industry.  Jim has been a partner at several major international law firms, and he previously served as Chief Legal and Administrative Officer for a large privately held company. 

Jim began his career as a commercial litigator and trial lawyer at a New York City-based firm, later moving to Chicago.  With both an eye for detail and an innate sense of the big picture, Jim quickly established a track record of helping businesses successfully navigate sensitive, complex disputes.  But he was particularly drawn to the opportunities his work presented to improve collaboration between business leaders and their lawyers.  Over time, Jim increasingly began serving as de facto general counsel to his smaller clients, advising on risk management, best practices, and various corporate and operational matters.

Jim transitioned in-house in 2016 and became his company's first general counsel.  While managing a team of in-house lawyers and legal ops professionals, Jim oversaw outside counsel and spearheaded countless internal projects, working closely with leaders in finance, HR, and operations.  Later, as a key member of his company's executive team, Jim leveraged his experience to optimize legal operations, creating synergies between business and legal functions. 

Jim founded Grindstone Advisory in 2023 to help legal teams become more valuable to their businesses, while helping businesses appreciate legal teams as more than just cost centers.