Michael Oleary
I Turn Governance into Outcomes | Connecting Strategy, Architecture & Funding in Complex Federal EnterprisesPrincipal Customer Success Executive-Federal
- Role
- Principal Customer Success Executive at ServiceNow
- Location
- Fredericksburg, VA, US
- LinkedIn followers
- 500 followers
About Michael Oleary
Most organizations don’t have a strategy problem—they have an execution gap.Governance exists. Architecture exists. Portfolio processes exist.But they rarely connect in a way that drives real outcomes.That’s where I operate.I work with federal and enterprise organizations to align governance, architecture, and portfolio decisions so they actually influence funding, delivery, and mission impact.My focus areas include:• Translating strategy into executable portfolio decisions• Connecting enterprise architecture to real-world delivery• Establishing governance that drives—not delays—outcomes• Integrating technical and economic decision-making (“techonomics”)I’ve spent my career working in complex, high-stakes environments where ambiguity is the norm and decisions have real consequences.If you’re trying to close the gap between strategy and execution—or seeing friction between governance and delivery—I’m always interested in comparing notes.My background in Electronic Warfare, installation management, and transformation gives me an end-to-end understanding of how technology enables strategic advantage. But my real focus is on translating complexity into action—advising leaders, shaping initiatives, and building systems that actually work under pressure.As a graduate of National Defense University, with an MA in Strategic Security Studies focused on Counterterrorism, I bring both strategic insight and operational experience. Today, I’m particularly interested in how AI and data-driven decision frameworks are reshaping defense and government IT landscapes.I regularly advise on transformation initiatives, speak on the challenges of secure tech adoption, and mentor emerging leaders in the field. If you’re building the next wave of mission-ready digital infrastructure—we should talk.
Experience
Principal Customer Success Executive
Nov 2025 — Present · Vienna, VA, US
Education
Institute for Veterans and Military Families - IVMF
Project Management
Drexel University
BS, Electrical Engineering
1990 — 1994
U.S. Naval War College
Masters of Arts, National Security and Strategic Studies
2003 — 2004
National Defense University
Master of Arts (MA) in Strategic Security Studies, Counter Terrorism
2014 — 2015
Texas McCombs School of Business
Postgraduate Program Certification via Great Learning, Cloud Computing
Skills
- Military Aviation
- Interagency Coordination
- Counterinsurgency
- Force Protection
- U.s. Department of Defense
- Top Secret
- Intelligence Analysis
- Security Clearance
- Electronic Warfare
- Flight Safety
- Aviation Operations
- Afghanistan
- Reconnaissance
- Homeland Security
- Radar
- Military Liaison
- Air Force
- Aircraft Carrier Flight Operations
- Operational Planning
- Counterterrorism
- Defense
- Flights
- Systems Engineering
- Government
- Military Operations
- Information Assurance
- Command
- Tactics
- Strategic Studies
- Weapons Handling
- Military
- Aviation
- Dod
- National Security
- Situational Leadership
- Navy
- Special Operations
- Aviation Safety
- Nato
- Strategic Vision
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