President Cleary's career began as an Enlisted Avionics Technician and in November 2023 he concluded a tour as the inaugural Principal Cyber Advisor (PCA) of the Department of the Navy, a Senior Executive Service (SES) role equivalent in rank to a three-star general/flag officer. In the MCPA, he has served as the inaugural National Capital Region (NCR) Chapter President and on the Board of Directors.

First Commander of US Cyber Command (USCYBERCOM) and former Director of the National Security Agency (NSA)

Former Director of the Central Intelligence Agency (CIA) and National Security Agency (NSA)

Former Commander of US Army Cyber Command (ARCYBER)

Former Deputy Commander of US European Command (EUCOM)

Former Deputy Director of National Intelligence (DNI) and Sergeant at Arms of the US Senate

Inaugural/former Commander of US Army Cyber Command (ARCYBER)

Former G2 (Director of Intelligence) of the US Army and Commander of the Intelligence and Security Command (INSCOM)

Former Commander of 24th Air Force (Air Forces Cyber) and USCYBERCOM J5

Former Commander of the Cyber National Mission Force and 10th Fleet. He serves as the inaugural Chairman of the MCPA Board of Advisors.

Commander of the 4th Marine Aircraft Wing, and Former Deputy Commanding General of Marine Corps Forces Cyberspace Command and Deputy Commander of Joint Task Force-ARES

Former J2 (Director of Intelligence) at the Joint Staff (JS) and PACOM

Former Chief of Staff and J5 at USCYBERCOM

Former Principal Director for Cyber Policy at the Office of the Secretary of Defense, Acting Deputy Assistant Secretary of Defense (DASD) for Cyber Policy, and Director of Current Operations at USCYBERCOM

Associate Dean of Joint Warfighting at the National Defense University's College of Information and Cyberspace (NDU CIC) and former inaugural Director of the Army’s Artificial Intelligence (AI) Task Force

Former Director of Operations at USCYBERCOM and inaugural COmmander of the CNMF, and current Senior Advisor at USCYBERCOM

Former Director of Cyber, Electronic Warfare, and Information Operations for the US Army, and Deputy Commanding General of US Army Cyber Command (ARCYBER)

Deputy Commander of the Cyber National Mission Force (CNMF)

Former Chancellor of the National Defense University (NDU) College of Information and Cyberspace (CIC), and Deputy Chief Information Officer (CIO) of the Department of Defense (DoD)

Former J2 (Director of Intelligence) at EUCOM and Director of the NSA National Security Operations Center

Former Chief of Staff of USCYBERCOM

Former Commander of CECOM and CENTCOM J6

Former Deputy Commander of US Fleet Cyber Command / US 10th Fleet

Former Director of Cyber Operations and Chief Information Security Officer (CISO) of the US Air Force

Former Cyber Command J7 and US Coast Guard First District Commander (D1)

Executive Director of the US Cyberspace Solarium Commission, former Policy Director of the Senate Armed Services Committee, and J3 (Director of Operations) of PACOM

Former J3 (Director of Operations) at EUCOM

Former Deputy Commander of 2nd Fleet and Joint Staff J7 Reserve Deputy Director

Former Senior Military Advisor for Cyber Policy to the Under Secretary of Defense for Policy

Former US Navy N2N6 and J2 (Intelligence Officer) of US Pacific Command (PACOM)

Former CIO and Advisor to multiple organizations

Former Commander of the Space and Naval Warfare Systems Command (SPAWAR)

Former Chief Information Officer (CIO) of the US Air Force

Chief of Staff and former J5 of US Cyber Command

Special Assistant to the Director of the Army National Guard for US Army Cyber Matters and Chief of Cyber Operations and the Cybersecurity and Infrastructure Security Agency (CISA)

Former Deputy Assistant Secretary of Defense (DASD) for Cyber Policy and Commander of 24th Air Force / Air Forces Cyber / Joint Force Headquarters-Cyber 

Former Assistant to the Director of the Defense Information Systems Agency (DISA) and Chief Information Security Officer (CISO) of the Army

Assistant Adjutant General - Air and Commander of the Delaware Air National Guard, and former Chief of Cyber Operations at US Special Operations Command (USSOCOM)

Former Army Chief of Cyber and Commandant of the Army Cyber School

Mobilization Assistant to the Assistant Secretary of the Air Force for Manpower and Reserve Affairs

Vice President of the State Guard Association of the United States (SGAUS) and current Commanding General of the Maryland Defense Force (Title 32)

Former Assistant Deputy Chief of Staff for Cyber Effects Operations at the Air Force Headquarters (AF A2/6)

National Guard Advisor to the 16th Air Force (Air Force Cyber) Commander and former Cyber National Mission Force (CNMF) Deputy Commander

Deputy J5 of USCYBERCOM and former Commander of the 175th Cyberspace Operations Group (COG)

Director of Cyberspace and Information Dominance at Air Combat Command

Board Chairman of the Air and Space Force Association, Commissioner of the CyberPatriot Program, and former Chief Information Officer (CIO) of the Pacific Air Forces

Former Senior Director for Strategic Planning on the National Security Council

Inaugural/former Chief Information Security Officer (CISO) of the United States

Former Strategic Initiatives Chief at USCYBERCOM

Inaugural Senior Technical Advisor of Joint Force Headquarters - Department of Defense Information Network (JTF-DODIN) and Lead Warrant for Developing Field Manual (FM) 3-12 Cyberspace and Electromagnetic Warfare

Former Senior Enlisted Leader (SEL) of USCYBERCOM and NSA

Former SEL of USCYBERCOM and NSA

Former SEL of US Space Command (USSPACECOM), USCYBERCOM, and NSA

Former Associate Director of Intelligence at USCYBERCOM

Former President of The Institute of World Politics (IWP), Deputy Under Secretary of Defense for Policy, and Assistant Secretary of Defense for Strategy, Plans, and Capabilities

Former Assistant Director of the DHS Cybersecurity and Infrastructure Security Agency (CISA), former Director of the National Cybersecurity and Communications Integration Center (NCCIC), and former Deputy Commander of US Coast Guard Cyber Command

Former Deputy Director of the NSA for Compliance and former Commandant of the National Cryptologic School (now University)

Head of US Defense Strategy at Amazon Web Services, former Chief of Staff to the DoD CIO, and lead for the 2018 DoD Cyber Strategy and Cyber Posture Review

Deputy Assistant National Cyber Director in the White House and former Principal Director for Cyber in the Office of the Under Secretary of Defense (USD) for Research and Engineering (R&E)

Former Director for Cybersecurity Policy at the National Security Council and Chief Technology Officer for the DoD CIO

Former Deputy Assistant Secretary of Defense (DASD) for Cyber Policy and Chancellor (Acting) of the National Defense University (NDU) College of Information and Cyberspace (CIC)

Deputy National Cyber Director

Founder of Blacks In Cybersecurity

Founder of Raíces Cyber

Founder of the Information Professionals Association

Former President of the Association for Computing Machinery (ACM) and Director of the Cebrowski Institute at the Naval Postgraduate School

Chief Federal Security Officer at Microsoft

Co-founder of Tenable and Gula Tech Foundation

Former Cyber Strategist at the Officer of the National Cyber Director and founding Director of the Cyber Statecraft Initiative at the Atlantic Council

Founder and CEO, Dragos, Inc.

Founder of TheIntelligenceCommunity.com (TIC), Foreign Area Officer Association (FAOA) Board Member, and Editor in Chief of the peer reviewed journal "International Affairs"

Research Professor at the Naval Postgraduate School

President of Capitol Technology University

CEO of the Technology Advancement Center (TAC)

Executive Director of the Carolina Cyber Network

Director of the Center for Cyber Security Studies at the US Naval Academy and former Deputy Assistant National Cyber Director in the White House

Former Director of the Defense Intelligence Agency (DIA), Deputy Commander of US Cyber Command (USCYBERCOM), and Commander of Marine Corps Forces Cyber Command (MARFORCYBER). MCPA Advisor 2000-2023.

Former Director of Current Operations at USCYBERCOM