For 30 years, Cary has worked with Senior Executives and Boards on challenging and complex strategic issues. In addition to his expertise in strategy workshop design and facilitation, Cary leads SOG’s efforts focusing on large-scale transformation and strategy programs. These include strategy formulation and execution, executive and organizational alignment, and performance measurement. Cary's work has spanned the financial services, healthcare, retail, manufacturing, business services, software, energy, education, consumer products and transportation industries in North America and Europe.​​

Cary’s book Simple Sabotage: A Modern Field Manual for Detecting & Rooting Out Everyday Behaviors That Undermine Your Workplace, (co-authored with Bob Frisch and Rob Galford) was published by HarperCollins and became a best seller in the management category. His work has been published in Fast Company, The Daily Beast and Workforce. Harvard Business Review has published 15 of Cary’s articles, including “Leadership Summits That Work” (Harvard Business Review, co-authored with Bob Frisch).  Several of his articles are featured in HBR Guides to Making Every Meeting Matter, to Making Better Decisions, to Remote Work, to Collaborative Teams, and to Managing Flexible Work, as well as HBR’s Special Issue: How to Make Decisions Amid Chaos. ​

Prior to joining the Strategic Offsites Group, Cary led the Finance practice at the Palladium Group, where he worked closely with David Norton and Robert Kaplan (co-creators of the Balanced Scorecard) to pioneer Palladium’s “Planning for Results” offering. Previously, Cary co-founded Painted Word, a strategy and technology consulting firm, where he established and managed the firm’s Strategy and Financial Services practices. Inc. magazine twice named Painted Word to the Inc. 500 as one of the fastest-growing privately held companies. Cary led the process to sell Painted Word to Monitor Clipper Partners, a private equity firm, and the subsequent merger with the Balanced Scorecard Collaborative to form the Palladium Group.​

Before founding Painted Word, Cary worked for Kearney, a global management consulting firm. He began his career in investment banking at Prudential-Bache Capital Funding, where he was an Associate in the Financial Institutions Group. ​​

Cary earned a BA with Highest Distinction from the University of Virginia and holds a MBA from Harvard Business School. Cary recently served on the Board of Trustees for the International School of Boston and currently serves on the Board of Trustees for ECRI, a non-profit organization dedicated to improving the safety, quality, and cost-effectiveness of care across all healthcare settings.