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War Room to Board RoomAuthor: MaShon Wilson
This short episode overviews all the topics we plan to cover: transitions, careers, and leadership. Some topics include: Preparing to Transition (18-24 months out), Finances, VA/Medical, Positioning yourself, Career, Networking, and Management/Leadership Challenges. Hosted on Acast. See acast.com/privacy for more information. Language: en Genres: Business, Careers, Management Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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S. 4 Ep. 2 - Ross Dickman - Aviator/TAC Officer to Non-Profit Executive
Episode 2
Tuesday, 18 November, 2025
Ross Dickman is Chief Executive Officer of Hire Heroes USA, the nation's leading employment support nonprofit serving transitioning service members, veterans, and military spouses. A West Point graduate and Army veteran, Ross exemplifies successful military-to-civilian transition while helping thousands of veterans achieve the same.Military LeadershipRoss graduated from the United States Military Academy at West Point with a BS in Comparative Politics (2000-2004). His Army career included commanding an Apache Longbow helicopter company of 35 soldiers and 8 aircraft worth over $500 million. Selected ahead of 10 peers, he also commanded a Headquarters Company of 115 soldiers with $12+ million in equipment.His operational roles included serving as Operations Manager for the 1st Air Cavalry Brigade (3,500 soldiers, 120 aircraft), Platoon Leader managing 16 soldiers and 4 aircraft valued at $200+ million, and Logistics Manager for a battalion of 420 soldiers. His final military assignment was Executive Assistant to the Commanding General at the U.S. Army Combat Readiness and Safety Center, coordinating operations and strategic communications for senior leadership.Advanced EducationRoss earned his MA in Organizational Psychology from Teachers College at Columbia University (2012-2013) through the Eisenhower Leader Development Program, a selective partnership between Columbia and West Point. He later completed his Executive MBA from the Terry College of Business at the University of Georgia (2018-2020), combining organizational psychology insights with strategic business expertise.Hire Heroes USA JourneyRoss joined Hire Heroes USA in March 2016 as Director of the Independence Project, managing a $13 million, five-year research program examining veteran interactions with the VA disability system. He led program design, data analysis, and a six-person team while managing relationships with major partners and funders.His leadership drove rapid advancement: Interim CEO (February 2020), Chief Operating Officer (October 2020-April 2024), and Chief Executive Officer (March 2024-present). Under his leadership, Hire Heroes USA maintains its position as America's most impactful veterans employment organization.Leadership PhilosophyRoss operates at the intersection of operational efficiency and strategic vision, believing in collaborative problem-solving, relationship building, and evidence-informed processes. He views employment as the primary vehicle for quality of life and community inclusion after military service, driving his commitment to full lifecycle career interventions that impact veterans, families, communities, and the nation.Selected as a Stand-To Veteran Leadership Program Scholar at the George W. Bush Presidential Center (2021), Ross continues developing veteran leaders committed to service beyond uniform.Impact & VisionRoss's journey from commanding combat aircraft to leading the nation's premier veterans employment organization demonstrates adaptive leadership and mission-driven excellence. His combination of military discipline, organizational psychology expertise, and business strategy enables Hire Heroes USA to provide personalized, no-cost employment services that transform thousands of lives annually—ensuring successful reintegration and meaningful civilian careers for America's veterans. Hosted on Acast. See acast.com/privacy for more information.
