The Winmill Group, LLC

Jason Winmill, MBA

Jason Winmill has over 15 years of management and strategy consulting experience. His specialty is consulting to large corporate groups on their most important management issues. Jason has advised senior executives (including general counsels and chief executives) across a range of industries including healthcare, government, pharmaceuticals, retail, consumer products, financial services/insurance and utilities.

Jason has led consulting engagements for major corporate legal groups focusing on  pre- and post-merger integration support, development of advanced management systems and tools (such as budgeting processes and Early Case Assessments), legal organizational design and restructuring and law department benchmarking. 

Jason’s work has been featured in publications such as the Wall Street Journal, Corporate Counsel Magazine, the ACC Docket, The American Lawyer, Inside Litigation, Purchasing Magazine and Inside Supply Management. Jason has held positions at Bain & Co—a leading strategy consulting firm and at Goodmeasure Consulting, a leading organizational change consulting firm headed by Harvard Business School faculty, a former editor of the Harvard Business Review and leader of the Harvard Business School’s general management faculty.

Jason is an honors graduate of Harvard College.  He received an MBA from the Harvard Business School, where he was elected to lead the school’s Forum on Business Ethics.


The following Principals assemble and oversee each team utilized by the Winmill Group.

Ryan Winmill, JD

Ryan has worked extensively on security planning and preparedness projects and is a leading expert in the field. From 2003 to 2004, Ryan served as the Homeland Security Specialist for the Commonwealth of Massachusetts Executive Office of Public Safety (EOPS). In that capacity, Ryan was responsible for the Boston Urban Area Security Initiative Budget of $21 million. Ryan also served with the U.S. Department of Homeland Security, where he managed exercise activities in 15 states, from 2005 to 2007.  In 2007, Ryan entered the private sector as a consultant. His planning and exercise resume includes projects with the following federal and state entities: U.S. Department of Homeland Security, FEMA, Massachusetts Emergency Management Agency, Massachusetts Department of Public Health, District of Columbia Homeland Security and Emergency Management Agency, Department of Defense, U.S. Coast Guard, Center for Disease Control and Prevention, the Federal Bureau of Investigation, the Louisiana Governor’s Office of Homeland Security and Emergency Preparedness, and the U.S. Secret Service, among others. 

Ryan has received FEMA certifications in National Incident Management System (NIMS), Incident Command System (ICS), and Exercise Management. While with the Massachusetts Executive Office of Public Safety, Ryan authored the 2004 Massachusetts Exercise Strategy, and while with the U.S. Department of Homeland Security, Ryan authored the 2006 Louisiana Hurricanes Katrina After Action Report, contributed to the Hurricane Katrina White House After Action Report, and most recently authored the first Louisiana Terrorism Incident Plan.

Ryan is the founder and President of the Winmill Group  and  is also a licensed attorney in Massachusetts.

Carlo Boccia

Carlo Boccia is an acknowledged and widely respected international and domestic security expert. He retired from the federal government after 33 years of distinguished military, intelligence and law enforcement service, during which time he was posted to six domestic and three foreign offices. His credits include two U.S. Attorney General’s Awards, several foreign government citations, and the prestigious Presidential Rank Citation for outstanding achievement.

Carlo served as the Director of Emergency Management for the City of Boston and the Director of Homeland Security for the Metro-Boston Region from April 2004 through March 2007. He oversaw the initiation and supervision of a comprehensive emergency management plan for the entire region including an evacuation, port security planning and a region wide inter-operable communications plan, both of which are recognized benchmarks used by the U.S. Department of Homeland Security. Carlo chaired the Region’s nine city-specific crisis management planning committees and served as an executive board member of the “Big City” emergency management association consisting of New York, Washington, D.C., Los Angeles, Chicago, Miami, San Francisco and Boston.  Carlo is a national-level expert in hazard mitigation planning based on his emergency planning and response experience, and frequently advises clients, including universities, on such matters.

Carlo ended his federal career in 1997 as the Special Agent in Charge of the New York Division of the U.S. Drug Enforcement Agency (DEA). Carlo’s duties included the development and management of the premier money laundering and financial/narco-terrorism program in the agency.  His DEA service included assignment as the Special Agent in Charge of the New England Division (1991 - 1994) and as an attaché to Paris, France (1987 - 1991). Carlo is a graduate of the Citadel.