Raynor was born in Brantford, Ontario, attended Appleby College in Oakville, Ontario, and holds an undergraduate degree in Philosophy from Harvard College (1990) in Cambridge, MA, where he graduated Magna cum Laude.

During the course of his undergraduate career he was a Detur Prize winner (first year academic excellence) and a John Harvard Scholar (continued academic excellence). His honors thesis examined the metaphysics of personal identity. He has an MBA (1994) from the Richard Ivey School of Business in London, Ontario where he was awarded the Nelson M. Davis Memorial Scholarship. He earned his Doctorate in Business Administration (DBA) from the Harvard Business School (2000), where he was a Dively Award winner for research excellence.

Raynor’s first book, co-authored with Clayton M. Christensen, The Innovator's Solution, was a bestseller [1] [2] published in 2003. The primary focus of the book was on creating and sustaining successful growth. Raynor’s second book, The Strategy Paradox (ISBN 978-0-385-51622-8), was published by Currency/Doubleday in February 2007.[3][4]