Kingsley has been at the forefront of technology innovation in the legal practice. He has 30 years of experience in the practice of law, software design and development, strategy and management. In 2012, Kingsley was recognized by the ABA as a Legal Rebel. In 2013, he was honored as one of the Fastcase 50; an Innovator by Law Technology News; and a national Law Journal Trailblazer and Pioneer.

Kingsley developed some of the first document assembly systems. He taught himself the C computer language and automated his tax practice. Later, Kingsley was one of the leading innovators in developing the theory and practice of knowledge management. He wrote the Knowledge Management Workbook.

Next, Kingsley pioneered the new discipline called contract analysis. He is a founder of KMStandards and has developed software capable of automatically analyzing legal agreements and creating contract standards. Using this software, Kingsley has developed the free web resource ContractStandards.com providing model contracts, checklists, and clauses, together with other contract resources. Kingsley is also a founder of Akorda.com a startup applying AI to contract review.

Kingsley holds law degrees from Oxford University (First Class Honours) and Harvard Law School.